Tag: M.W:100-200

Safety of 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about NMR and uv spectral studies of some 1-aryl-substituted 3-methyl-2-phospholene oxides. Author is Kerek, F.; Ostrogovich, G..

The NMR and uv spectra of 7 1-aryl-3-methyl-2-phospholene oxides (I, R = H, Me, NMe2, etc.) are discussed. The value of 25 cps for the coupling constants of the P atom with vinylic protons indicates a Δ2,3 position of the phospholene ring double bond. The linear correlation of the bathochromic shift values with substituent constants (σ°) shows a low conjugative interaction between the benzene ring and the phosphoryl group.

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

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《2- and 5-Fluoronicotinic acids》. Authors are Beaty, R. D.; Musgrave, W. K. R..The article about the compound:Methyl 5-fluoro-3-pyridinecarboxylatecas:455-70-9,SMILESS:COC(=O)C1=CC(F)=CN=C1).Name: Methyl 5-fluoro-3-pyridinecarboxylate. Through the article, more information about this compound (cas:455-70-9) is conveyed.

5-Aminonicotinic acid (I) (3 g.) in 20 cc. 40% HBF4 at -5° treated with 2.5 g. NaNO2, the mixture kept 1 h., heated 30 min. at 50°, neutralized with Na2CO3, and the resulting salt refluxed 2-3 h. with 3% MeOH-H2SO4, gives 0.3 g. Me 5-fluoronicotinate, m. 48°. The 2-isomer of I (2 g.) in 10 cc. 40% HBF4, diazotized with 1 g. NaNO2 in 10 cc. H2O at 0 to -5°, and the solution kept 1 h. at 0°, heated 1 h. at 50-60°, and basified to pH 5 with NaOH, gives 33% 2-fluoronicotinic acid, m. 164-5°; the Me ester m. 74-5° and the amide m. 124°. 3-Fluoropicolinic acid could not be prepared by this method.

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

Related Products of 707-61-9. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Phospho sugars; novel preparation and their glycosyl compounds. Author is Ikai, Koichi; Iida, Akihito; Yamashita, Mitsuji.

Treatment of 1-phenyl-2-, and -3-phospholene 1-oxides with NBS affords 4-bromo-1-phenyl-2-phospholene 1-oxide (I). Substitution of the bromide with acetate, followed by stereoselective oxidation with osmium tetroxide and peracetylation with acetic anhydride/pyridine affords phospho sugar derivatives II of tetrafuranose. Furthermore, glycosyl compounds III (R = iodo, OAc, SCN, N3) of phospho sugars were prepared from 3-methyl-1-phenyl-2-phospholene 1-oxide by bromination and nucleophilic substitution reactions.

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

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Bromomethyl-1,3-dioxolane(SMILESS: BrCC1OCCO1,cas:4360-63-8) is researched.Category: chiral-oxygen-ligands. The article 《Modular Synthesis of Bicyclic and Tricyclic (Aza-) Arenes from Nucleophilic (Aza-)Arenes with Electrophilic Side Arms via [4+2] Annulation Reactions》 in relation to this compound, is published in Advanced Synthesis & Catalysis. Let’s take a look at the latest research on this compound (cas:4360-63-8).

An efficient strategy for the synthesis of bicyclic aza-arenes I [R1 = Me, Ph, 2-thienyl, etc.; R2 = Me, OEt, OBn, etc.; Ar = OMe, Cl, Ph, etc.] and tricyclic aza-arenes, e.g., II from a nucleophilic aza-arene with an electrophilic side arm was developed. The aza-arene precursor had both nucleophilic and electrophilic sites, which were fixed at a 1,4-distance. The bicyclic and tricyclic (aza-)arene products I and II were constructed via [4+2] annulation by using scandium(III) triflate as a catalyst and enolizable ketones or aldehydes as the counterpart reagents. A variety of six-membered carbocycles and heterocycles, such as indolizines, indoles, naphthalenes, carbazoles and pyrido[1,2-α]indoles, were successfully synthesized. Some one-pot sequential reactions were also developed, in which the 1,4-donor-acceptor precursors can be synthesized via oxidation of alcs. or a proper condensation reaction.

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

HPLC of Formula: 707-61-9. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis. Author is Marsden, Stephen P.; McGonagle, Alison E.; McKeever-Abbas, Ben.

The first examples of heterocycle synthesis by iminophosphorane formation/intramol. aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. E.g., in presence of phospholene oxide I, reaction of isocyanate 2-OCNC6H4C6H4CO2Me-2, formed from acyl azide 2-N3COC6H4C6H4CO2Me-2 by Curtius rearrangement, gave 71% phenanthridine II. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ IR spectroscopy.

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

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 4360-63-8, is researched, Molecular C4H7BrO2, about Modular Synthesis of Bicyclic and Tricyclic (Aza-) Arenes from Nucleophilic (Aza-)Arenes with Electrophilic Side Arms via [4+2] Annulation Reactions, the main research direction is bicyclic aza arene preparation; tricyclic aza arene preparation; enolizable carbonyl compound aza arene annulation scandium triflate catalyst.Name: 2-Bromomethyl-1,3-dioxolane.

An efficient strategy for the synthesis of bicyclic aza-arenes I [R1 = Me, Ph, 2-thienyl, etc.; R2 = Me, OEt, OBn, etc.; Ar = OMe, Cl, Ph, etc.] and tricyclic aza-arenes, e.g., II from a nucleophilic aza-arene with an electrophilic side arm was developed. The aza-arene precursor had both nucleophilic and electrophilic sites, which were fixed at a 1,4-distance. The bicyclic and tricyclic (aza-)arene products I and II were constructed via [4+2] annulation by using scandium(III) triflate as a catalyst and enolizable ketones or aldehydes as the counterpart reagents. A variety of six-membered carbocycles and heterocycles, such as indolizines, indoles, naphthalenes, carbazoles and pyrido[1,2-α]indoles, were successfully synthesized. Some one-pot sequential reactions were also developed, in which the 1,4-donor-acceptor precursors can be synthesized via oxidation of alcs. or a proper condensation reaction.

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

Quality Control of 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Synthesis of some 1-aryl-2,3-dibromophospholanes as novel anti-cancer agents. Author is Yamada, Manabu; Asai, Kazuhide; Yamashita, Junko; Suyama, Takuya; Niimi, Taishi; Maddali, Kasthuraiah; Fujie, Michio; Nakamura, Satoki; Kimura, Motohiko; Tanaka, Yasutaka; Toda, Mitsuo; Yamashita, Mitsuji.

Novel phosphorus heterocyclic compounds, 3-methyl-1-(3-bromophenyl as well as some 3-substituted phenyl)-2-phospholene 1-oxides, were synthesized from 1-phenyl-2-phospholene 1-oxide via 3-methyl-1-(3-nitrophenyl)-2-phospholene 1-oxide. 1-(4-Bromophenyl)-2-phospholene was prepared by Grignard coupling reaction of 1-chloro-3-methyl-2-phospholene 1-oxide with 4-bromophenylmagnesium bromide. 2,3-Dibromo-3-methyl-1-arylphospholane 1-oxides were prepared by the addition reaction of bromine to the C=C double bond of 2-phospholenes. The substituent effect of the Ph group of the 1-aryl-phospholanes on the observed anti-proliferative effect against U937 leukemia cell lines evaluated by MTT in vitro methods showed that 2,3-dibromo-3-methyl-1-(4-bromophenyl)phospholane was the most active among 1-arylphospholanes. These novel dibromophosphorus heterocyclic derivatives exhibit much higher anticancer activity than Gleevec (mol. targeting chemotherapeutic agent) against U937 cells.

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

Zhou, Zhenhua published the article 《A chiral shift reagent for measurement of optical purities of chiral phosphine oxides》. Keywords: phosphine oxide optical purity determination; NMR phosphine oxide optical purity determination; phenylmethylphospholene optical purity determination; phospholene methylphenyl optical purity determination; nitrobenzoylphenylethylamine chiral shift reagent NMR.They researched the compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide( cas:707-61-9 ).HPLC of Formula: 707-61-9. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:707-61-9) here.

(R)-(-)-N-(3,5-Dinitrobenzyl)-α-phenylethylamine (I) is an excellent chiral shift reagent for measurement of optical purities of chiral phosphine oxides. The method of preparation and application of reagent I are discussed in detail. 1-Phenyl-3-methyl-2-phospholene(II) is oxidized to 1-phenyl-3-methyl-2-phospholene 1-oxide (III) which is then reacted with tert-BuOOH with complete retention of optical activity. When phosphine oxide is mixed with reagent(I), optical purity of phosphine oxide can be measured according to 1H NMR spectra; the optical purity of II can be determined

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

Nallagonda, Rajender; Karimov, Rashad R. published the article 《Copper-Catalyzed Regio- and Diastereoselective Additions of Boron-Stabilized Carbanions to Heteroarenium Salts: Synthesis of Azaheterocycles Containing Contiguous Stereocenters》. Keywords: nonaromatic nitrogen heterocycle preparation diastereoselective addition boron carbanion heteroarenium.They researched the compound: Methyl 5-fluoro-3-pyridinecarboxylate( cas:455-70-9 ).Product Details of 455-70-9. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:455-70-9) here.

Nucleophilic addition of diborylalkyl reagents to N-alkyl or N-acylpyridinium and related heteroarenium salts has been developed as a key step for the synthesis of nonaromatic nitrogen heterocycles that contain contiguous stereogenic centers. Derivatization of the dihydropyridine products for the synthesis of tetrahydropyridines and piperidines have also been described.

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

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 4360-63-8, is researched, SMILESS is BrCC1OCCO1, Molecular C4H7BrO2Journal, Article, Research Support, Non-U.S. Gov’t, Organic Letters called Synthesis of Cyclic Amidines by Iridium-Catalyzed Deoxygenative Reduction of Lactams and Tandem Reaction with Sulfonyl Azides, Author is He, Youliang; Wang, Xiaoming, the main research direction is cyclic amidine diastereoselective preparation; iridium catalyst reductive deoxygenation lactam amidation sulfonyl azide.Computed Properties of C4H7BrO2.

An efficient and convenient synthesis of various cyclic amidines has been achieved via iridium-catalyzed deoxygenative reduction of lactams with a silane followed by a one-pot cycloaddition reaction with sulfonyl azides. Using the novel tandem procedure, a large array of cyclic amidines bearing various sized rings were synthesized in good yields from readily available lactams. This methodol. has been successfully utilized in the late stage diversification of complex architectures bearing a lactam moiety.

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