Category: Dioxole

On April 1, 2011, Brock, E. Anne; Davies, Stephen G.; Lee, James A.; Roberts, Paul M.; Thomson, James E. published an article.Computed Properties of 38838-06-1 The title of the article was Asymmetric Synthesis of Polyhydroxylated Pyrrolizidines via Transannular Iodoamination with Concomitant N-Debenzylation. And the article contained the following:

The doubly diastereoselective “matched” conjugate addition of lithium (R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amide to tert-Bu (4S,5R,E)-4,5-O-isopropylidene-2,7-dienoate (derived from D-ribose in 3 steps) and in situ enolate oxidation with (-)-camphorsulfonyloxaziridine was followed by ring-closing metathesis with Grubbs I to give a hexahydroazocine scaffold. Subsequent treatment with I2 resulted in transannular iodoamination accompanied by loss of the α-methyl-p-methoxybenzyl group to give the corresponding pyrrolizidine scaffold as a single diastereoisomer upon direct crystallization from the crude reaction mixture Further functional group manipulations enabled the preparation of (-)-7a-epi-hyacinthacine A1 (I). The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Computed Properties of 38838-06-1

The Article related to enantioselective synthesis polyhydroxylated pyrrolizidine iodoamination debenzylation, hyacinthacine a1 enantioselective synthesis, Alkaloids: Alkaloids Containing One Nitrogen Atom At A Bridgehead and other aspects.Computed Properties of 38838-06-1

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

On June 12, 2014, Rancati, Fabio; Linney, Ian published a patent.Application of 124038-36-4 The title of the patent was Preparation of compounds having muscarinic receptor antagonist and β2 adrenergic receptor agonist activity. And the patent contained the following:

The present invention relates to the preparation of heterocyclic containing quinuclidine ester compounds acting both as muscarinic receptor antagonists and β2 adrenergic receptor agonists. For example, compound I was prepared in several steps via the coupling of alc. II with acid III. The experimental process involved the reaction of Methyl 3-(1,3-dioxolan-2-yl)benzoate(cas: 124038-36-4).Application of 124038-36-4

The Article related to quinuclidine ester preparation muscarinic receptor antagonist, adrenergic receptor agonist quinuclidine ester, Alkaloids: Alkaloids Containing One Nitrogen Atom At A Bridgehead and other aspects.Application of 124038-36-4

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

On June 12, 2014, Rancati, Fabio; Linney, Ian; Knight, Chris; Schmidt, Wolfgang published a patent.Synthetic Route of 124038-36-4 The title of the patent was Preparation of compounds having muscarinic receptor antagonist and beta2 adrenergic receptor agonist activity. And the patent contained the following:

The present invention relates to compounds I [wherein: Q is a group of formula Q1, Q2 and Q3; Z is H or OH; Y is selected from A1B(CH2)n1A2CD(CH2)mE and A1CBC’D(CH2)pE, which are divalent groups; wherein A1 and A2 are independently absent or are selected from the group consisting of C1-6-alkylene, C3-8-cycloalkylene and C3-8-heterocycloalkylene optionally substituted by one or more substituents selected from the group consisting of C1-6-alkyl, aryl-(C1-6-alkyl) and heteroaryl-(C1-6-alkyl);]. [B is absent or is selected from the group consisting of C3-8-cycloalkylene, C3-8-heterocycloalkylene, arylene and heteroarylene, optionally substituted by one or more groups selected from halogens, CN, linear or branched C1-6-alkyl, linear or branched C1-6-haloalkyl, C1-6-alkoxy, aryl, aryl-(C1-6-alkyl), NR7R8 and heteroaryl;C and C’ are absent or are independently selected from the group consisting of oxygen, C(:O), OC(:O) and -C(OO)- or one of the following:]. [NR7C(:O), O(CH2)nO2C, N((CH2)nCO2R7)SO2, NR7(CH2)nO2C, CO2(CH2)nNR7C(:O), N(COR7)(CH2)nO2C, O2CCR7R8NHC(:O), NR7CONR7′(CH2)nO2C, C(:O)NR7(CH2)nO2C, (CH2)O2C, SO2NR7(CH2)nO2C, C12, N(SO2R7)(CH2)nO2C, C14; wherein R7, R7′ and R8 are independently H or selected from the group consisting of linear or branched C1-6-alkyl, C3-8-cycloalkyl, (C3-8-cycloalkyl)-(C1-6-alkyl), (C3-8-heterocycloalkyl)-(C1-6-alkyl), aryl and aryl-(C1-6-alkyl), optionally substituted by one or more substituents selected from the group consisting of C1-6-alkyl, C1-6-haloalkyl, halogen atoms, C1-6-alkoxy and C1-6-alkoxy;]. [D is absent or is selected from the group consisting of C1-6-alkylene, arylene, heteroarylene and C3-8-heterocycloalkylene, optionally substituted by one or more C1-6-alkyl groups; n, n’, m and p are independently O or an integer from 1 to 3; E is absent or is selected from O and OC(:O); G is arylene optionally substituted by one or more substituents selected from the group consisting of halogen atoms, OH, oxo (:O), SH, NO2, CN and NH2;]. [R1 and R2 are independently H or selected from the group consisting of C1-6-alkyl and aryl, optionally substituted by one or more halogen atoms; M is NR3; R3 is H or C1-6-alkyl; R4 is a group of formula J1] acting both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists. Thus, 8-hydroxyquinolin-2-one derivative II was prepared from 3-hydroxybenzophenone via reductive amination with formamide; hydrolysis with HCl in MeOH; N-alkoxycarbonylation with di(tert-butyl) dicarbonate in CH2Cl2 containing EtN(CHMe2)2 followed by treatment with K2CO3 in MeOH; chromatog. resolution with CHIRALPAK® AD; etherification with 4-BrCH2C6H4CO2Me in MeCN containing K2CO3; hydrolysis with HCl in dioxane/MeOH; alkoxycarbonylation with (R)-quinuclidin-3-yl chloroformate (III) in pyridine;. Saponification with aqueous LiOH in THF; amidation with 3-(1,3-dioxolan-2-yl)propyl piperidine-4-carboxylate hydrochloride (IV·HCl) in DMF containing EtN(CHMe2)2 and HATU; deacetalation with aqueous HCl in THF; and reductive amination with of (R)-5-(2-amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one hydrochloride (V·HCl) in MeOH containing NaBH(OAc)3 and AcOH. The present invention also relates to processes for their preparation, to compositions comprising them, to therapeutic uses and combinations with other pharmaceutical active ingredients. The receptor activity of I was determined [the Ki values (calculated from IC50 values by the Cheng and Prusoff equation) of most of the compounds of the examples are less than 10 nM in the M3 Receptor and in the β2 adrenoceptor radioligand binding assays]. The experimental process involved the reaction of Methyl 3-(1,3-dioxolan-2-yl)benzoate(cas: 124038-36-4).Synthetic Route of 124038-36-4

The Article related to muscarinic receptor antagonist, beta2 adrenergic receptor agonist, Alkaloids: Alkaloids Containing One Nitrogen Atom At A Bridgehead and other aspects.Synthetic Route of 124038-36-4

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

On December 12, 2003, Verhelst, Steven H. L.; Martinez, Baltasar Paez; Timmer, Mattie S. M.; Lodder, Gerrit; Van der Marel, Gijsbert A.; Overkleeft, Herman S.; Van Boom, Jacques H. published an article.Synthetic Route of 38838-06-1 The title of the article was A Short Route toward Chiral, Polyhydroxylated Indolizidines and Quinolizidines. And the article contained the following:

In this paper, a rapid route toward functionalized bicyclic alkaloids is presented. In only three steps, an easily accessible carbohydrate derivative was converted into iodomethyl indolizidine I, which can equilibrate to the corresponding iodoquinolizidine II. We provide strong evidence that this equilibration proceeds via an aziridinium ion intermediate. Furthermore, nucleophilic substitution of the iodomethyl indolizidine as well as the aziridinium intermediate gives access to highly functionalized indolizidine and quinolizidine alkaloids. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Synthetic Route of 38838-06-1

The Article related to chiral polyhydroxylated indolizidine quinolizidine preparation, Alkaloids: Alkaloids Containing One Nitrogen Atom At A Bridgehead and other aspects.Synthetic Route of 38838-06-1

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

On December 31, 2016, Ajay, Sama; Arora, Inderpreet; Saidhareddy, Puli; Shaw, Arun K. published an article.COA of Formula: C9H15IO4 The title of the article was Diversity-Oriented Synthesis of cis-3,4-Dihydroxylated Piperidine and Its Higher Saturated and Unsaturated Homologues from D-Ribose and Their Glycosidase-Inhibition Study. And the article contained the following:

The synthesis of six-, seven-, and eight-membered cis-dihydroxy azacycles has been accomplished from D-ribose using Vasella reductive amination as a key step and utilization of hydroboration-oxidation, Mitsunobu reaction, and ring-closing metathesis (RCM) reactions in a facile manner. These homologous dihydroxylated heterocyclic scaffolds were subjected to the glycosidase inhibition assays. However, only a moderate inhibitory activity for three out of five compounds was observed against α-glucosidases with a high degree of selectivity. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).COA of Formula: C9H15IO4

The Article related to cis dihydroxy azacycle preparation glycosidase inhibitor, ribose reductive amination hydroboration oxidation mitsunobu ring closing metathesis, Heterocyclic Compounds (One Hetero Atom): Higher-Membered Rings and other aspects.COA of Formula: C9H15IO4

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

On February 3, 2005, Fryszman, Olga M.; Lang, Hengyuan; Lan, Jiong; Chang, Edcon; Fang, Yunfeng published a patent.Application In Synthesis of Methyl 3-(1,3-dioxolan-2-yl)benzoate The title of the patent was Preparation of 5-membered heterocycles, in particular pyrazoles and imidazoles, as p38 kinase inhibitors. And the patent contained the following:

Title compounds I of [wherein R1 = H, acyl, P(:O)(OH)2; R2 = H, halo, (un)substituted alkyl, alkylthio, alkylsulfinyl, etc.; G = hetero/aryl, aralkyl, cycloalkyl, etc.; B = hetero/aryl; A = 5-membered ring containing one or two heteroatoms in the ring; D = CONH2 and derivatives, (un)substituted heteroaryl; R5 = H, halo, halo/thio/alkyl, OH and derivatives, alkyl/amino, etc.; R6 = H, halo, alkyl, alkoxy; and their pharmaceutically acceptable derivatives] were prepared as p38 kinase, including p38α and p38β kinase, inhibitors. Thus, reacting 3-hydrazino-N-methoxy-4-methylbenzamide with NaNO2 in the presence of SnCl2, and cyclization of the hydrazine with 2-(3-iodobenzoyl)-3-phenylaminoacrylonitrile gave II. Selected I displayed IC50 values <1 μM in a p38α kinase inhibition assay. I are useful for the treatment, prevention, or amelioration of one or more symptoms of p38 kinase mediated diseases and disorders, e.g. inflammatory disease, autoimmune disease, etc. The experimental process involved the reaction of Methyl 3-(1,3-dioxolan-2-yl)benzoate(cas: 124038-36-4).Application In Synthesis of Methyl 3-(1,3-dioxolan-2-yl)benzoate

The Article related to imidazole preparation p38 kinase inhibitor inflammation immunomodulator, antiinflammatory agent pyrazole preparation p38 kinase inhibition autoimmune disease, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Application In Synthesis of Methyl 3-(1,3-dioxolan-2-yl)benzoate

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Rychnovsky, Scott D.; Powers, Jay P. published an article in 2001, the title of the article was Zinc/copper couple.SDS of cas: 38838-06-1 And the article contains the following content:

Properties and applications of zinc/copper couple, an activated form of zinc metal reagent that can be used for cyclopropanation and conjugate addition of alkyl iodides to enones are reviewed. Also used for preparation of dichloroketene and 2-oxyallyl cations for cycloaddition reactions. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).SDS of cas: 38838-06-1

The Article related to review zinc copper couple preparation property reactivity, Organometallic and Organometalloidal Compounds: Reviews and other aspects.SDS of cas: 38838-06-1

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

On December 1, 1995, Paquette, Leo A.; Bailey, Simon published an article.Related Products of 38838-06-1 The title of the article was Evaluation of D-Ribose as an Enantiopure Building Block for Construction of the C-Ring of Taxol and Its Congeners. And the article contained the following:

The enantiomerically pure (4S,5R)-4-[(Z)-2-iodovinyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane is shown to be readily available from D-ribose via a sequence involving zinc-promoted reductive unmasking of an aldehyde and homologation with (iodomethylene)triphenylphosphorane. The vinyl anion produced by halogen-metal exchange adds from the endo direction to an enantiopure ketone prepared from D-camphor. The resulting carbinol undergoes anionic oxy-Cope rearrangement and C-methylation with complete stereocontrol to set the appropriate C-3 stereochem. of taxol. Dihydroxylation of this intermediate brings about facile transannular hemiketalization. DIBAL-H reduction of this intermediate does not affect the hemiketal, but does reduce the acetonide regiospecifically. An unusual transannular hydride shift occurs during subsequent heating with dibutyltin oxide, as confirmed by x-ray crystallog. When transannular hemiketalization is skirted, hydroboration-oxidation of the side chain leads to an acetaldehyde which is notably prone to β-elimination. Treatment with potassium carbonate in methanol does eventuate in ring closure to give I via an aldol addition reaction, but only after methanol has been added in Michael fashion to the α,β-unsaturated aldehyde. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Related Products of 38838-06-1

The Article related to ribose enantiopure synthesis taxol ring, Terpenes and Terpenoids: Diterpenes (C20), Including Gibberellins, Retinoids, Quassinoids, and Tocopherols and other aspects.Related Products of 38838-06-1

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

On January 24, 2001, Alanine, Alexander; Buettelmann, Bernd; Heitz, Neidhart Marie-Paule; Jaeschke, Georg; Pinard, Emmanuel; Wyler, Rene published a patent.Application of 124038-36-4 The title of the patent was Triazole and imidazole derivatives, methods of preparation and use in treatment or prophylaxis of diseases caused by overactivation of respective NMDA receptor subtypes. And the patent contained the following:

The present invention relates to I wherein R1-R4 = H, CF3, OCF3, OCHF2, OCH2F, lower alkyl, lower alkoxy, halogen, hydroxy, Ph, benzyl, amino, nitro, pyrrol-1-yl, lower alkylsulfonyl, lower alkylthio, cyano or benzyloxy; or R2 and R3 may be together = O-(CH2)2-O-, -O-CH2-O-, -O-(CH2)2-, -(CH2)3- or CH:CH-CH:CH-; X = N:, imino with N possibly substituted, CH:; Y = -N:, :N-, imino with N possibly substituted, CH:; wherein one of X or Y has to be N; R5 = aminomethyl with N possibly substituted and to their pharmaceutically acceptable acid addition salts. The methods of preparation comprise cyclizing a carboxylic acid hydrazide with a benzenecarboximidamide hydrochloride or benzenecarboximidic acid ester to give a triazole; arylating a 4-iodo-2-phenylimidazole with a phenylboronic acid in the presence of Pd(PPh3)4 to give an imidazole; reducing II to the aminomethyl analog followed by di-N-alkylation using acyl chlorides and LiAlH4. These compounds may be used for the treatment or prophylaxis of diseases related to the N-methyl-D-aspartate (NMDA)-receptor-subtype selective blockers. Such diseases include acute forms of neurodegeneration caused, e.g., by stroke or brain trauma; chronic forms of neurodegeneration such as Alzheimer’s disease, Parkinson’s disease, Huntington’s disease or ALS (amyotrophic lateral sclerosis); neurodegeneration associated with bacterial or viral infections, and diseases such as schizophrenia, anxiety, depression and acute/chronic pain. The experimental process involved the reaction of Methyl 3-(1,3-dioxolan-2-yl)benzoate(cas: 124038-36-4).Application of 124038-36-4

The Article related to nmda receptor blocking triazole imidazole derivative preparation, glutamate receptor nmda binding blocking triazole imidazole derivative preparation, Heterocyclic Compounds (More Than One Hetero Atom): Other 5-Membered Rings, Two Or More Hetero Atoms and other aspects.Application of 124038-36-4

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

On February 5, 1992, Gilmore, Jeremy; Todd, Alec published a patent.Category: dioxole The title of the patent was Preparation of 5-[1-[(quinolylethenyl)benzyl]indol-7-yloxymethyl]tetrazoles and analogs as leukotriene antagonists. And the patent contained the following:

Title compounds [I; R = CR3R4C6H4YR5; R1 = H, halo, alkyl, alkoxy, etc.; R3, R4 = N, alkyl, (substituted) Ph, etc.; R5 = (substituted) heteroaryl; R6 = H, alkyl; 1 of R7, R8 = XR2 and the other = H; R2 = halo, cyano, CONH2, (protected) acid group, etc.; X = alkylene, oxyalkylene, etc.; Y = OCH2, CH2CH2, CH:CH, etc.] were prepared Thus, I (R1 = R6 = R8 = H) (II; R = H, R7 = OCH2CN) (preparation given) was condensed with quinolylethenylbenzyl chloride QCl and the product treated with Bu3SnN3 to give II (R = Q, R7 = 1H-tetrazol-5-ylmethoxy). I had pKb = 7-11 for dissociation of receptor inhibitor complexes in vitro. The experimental process involved the reaction of Methyl 3-(1,3-dioxolan-2-yl)benzoate(cas: 124038-36-4).Category: dioxole

The Article related to tetrazole quinolylethenylbenzylindolyloxymethyl preparation leukotriene antagonist, Heterocyclic Compounds (More Than One Hetero Atom): Other 5-Membered Rings, Two Or More Hetero Atoms and other aspects.Category: dioxole

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem