Category: 707-61-9

Product Details 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 A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via PIII/PV=O Redox Cycling. Author is Nykaza, Trevor V.; Harrison, Tyler S.; Ghosh, Avipsa; Putnik, Rachel A.; Radosevich, Alexander T..

A small-ring phosphacycle, 1,2,2,3,4,4-hexamethylphosphetane, is found to catalyze deoxygenative N-N bond-forming Cadogan heterocyclization of o-nitrobenzaldimines, o-nitroazobenzenes, and related substrates in the presence of hydrosilane terminal reductant [e.g., I → II (83%) in presence of phosphine oxide III.[O] and PhSiH3]. The reaction provides a chemoselective catalytic synthesis of 2H-indazoles, 2H-benzotriazoles, and related fused heterocyclic systems with good functional group compatibility. On the basis of both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV=O cycling, where DFT modeling suggests a turnover-limiting (3+1) cheletropic addition between the phosphetane catalyst and nitroarene substrate. Strain/distortion anal. of the (3+1) transition structure highlights the controlling role of frontier orbital effects underpinning the catalytic performance of the phosphetane.

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

Synthetic Route of C11H13OP. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about A chiral shift reagent for measurement of optical purities of chiral phosphine oxides. Author is Zhou, Zhenhua.

(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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1,3-Benzodioxole – Wikipedia,
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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《An efficient approach towards the stereospecific synthesis of epoxides from phospholene oxides》. Authors are Yamashita, Mitsuji; Krishna Reddy, Valluru; Rao, Lakonda Nagaprasada; Haritha, Buchammagari; Maeda, Motoki; Suzuki, Keiji; Totsuka, Hirono; Takahashi, Masaki; Oshikawa, Tatsuo.The article about the compound:4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxidecas:707-61-9,SMILESS:CC1=CP(CC1)(C2=CC=CC=C2)=O).Recommanded Product: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide. Through the article, more information about this compound (cas:707-61-9) is conveyed.

A novel method has been developed for stereospecific conversion of 2-phospholene 1-oxides into their corresponding 2,3-epoxides in high yields using sodium peroxide as a reagent. 2,3-Dihydro-1-phenyl-1H-phosphole 1-oxide (I) was inert to oxidation with 3-chloroperbenzoic acid; oxidation of I with bromine or N-bromoacetamide gave 2-bromo-3-hydroxy-1-phenylphospholane oxide as diastereomeric mixture and subsequent treatment of the bromohydrin gave a mixture of (1R,2S,5S)-rel-2-phenyl-6-Oxa-2-phosphabicyclo[3.1.0]hexane 2-oxide (erythro, II) and (1R,2R,5S)-rel-2-phenyl-6-Oxa-2-phosphabicyclo[3.1.0]hexane 2-oxide (threo). Epoxidation of I using sodium peroxide [Na2(O2)] gave II as a single diastereomer in 76% yield. 2,3-Dihydro-4-methyl-1-phenyl-1H-phosphole 1-oxide and 2,3-dihydro-1-methoxy-4-methyl-1H-phosphole 1-oxide failed to react with sodium peroxide [Na2(O2)]. The compounds thus prepared are intermediates for AZT analogs of phospha sugars (no data).

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

Quality Control of 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Improved syntheses and characterization of the isomers of 3-methyl-1-phenylphospholene 1-oxide. Author is Moedritzer, Kurt; Miller, Raymond E..

Isomerically pure 3-methyl-1-phenyl-2-phospholene 1-oxide and 3-methyl-1-phenyl-3-phospholene 1-oxide were prepared and characterized by 1H (60 and 270 MHz), 31P and 13C NMR, IR, Laser Raman, and mass spectrometry. 1,4-Cycloaddition of isoprene and PhPCl2 after hydrolysis of the addition product, yielded a mixture of the above 2-isomer and small amounts of 3-isomer from which pure 2-isomer was separated by fractional crystallization The analog reaction with PhPBr2 gave isomerically pure 3-isomer. An improved and shortened work-up procedure for the phospholene oxides was used resulting in higher yields.

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1,3-Benzodioxole – Wikipedia,
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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Structure of diene-phosphonous dihalide addition products and of derived phospholenes and phospholene oxides》. Authors are Quin, Louis D.; Gratz, Joan P.; Barket, Thomas P..The article about the compound:4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxidecas:707-61-9,SMILESS:CC1=CP(CC1)(C2=CC=CC=C2)=O).Related Products of 707-61-9. Through the article, more information about this compound (cas:707-61-9) is conveyed.

The cycloadducts of MePCl2 and butadiene, isoprene, 3,4-dimethylbutadiene, or piperylene give rise to 3-phospholene oxides on hydrolysis and 3-phospholenes (I) on reduction with Mg. The cycloadduct from butadiene also contained the 3-phospholene ring. The 3-phospholene oxides may be caused to rearrange to 2-phospholene oxides either thermally or by refluxing aqueous base. Acid treatment was effective only for rearranging the 3-Me derivative The 3,4-di-Me derivative resisted rearrangement conditions. PhPBr2 (synthesized by a new method from PhP(O)(OH)Cl and PBr3) also gave an adduct with isoprene shown by N.M.R. studies to contain the 3-phospholene ring, which was preserved in the oxide and phospholene. However, the isoprene-PhPCl2 adduct contained the 2-phospholene ring; the derived oxide and phospholene were also the 2-isomers. Independent syntheses of the isomeric 1-phenyl-3-methylphospholene oxides confirmed the assignments. The adduct from piperylene and PhPBr2 also gave on hydrolysis the 3-phospholene oxide, while that from PhPCl2 gave the 2-isomer. 26 references.

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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: 707-61-9, is researched, SMILESS is CC1=CP(CC1)(C2=CC=CC=C2)=O, Molecular C11H13OPJournal, Article, Journal of the American Chemical Society called A Phosphetane Catalyzes Deoxygenative Condensation of α-Keto Esters and Carboxylic Acids via PIII/PV=O Redox Cycling, Author is Zhao, Wei; Yan, Patrick K.; Radosevich, Alexander T., the main research direction is phosphetane catalyst preparation oxygenative condensation ketoester carboxylic acid.Application of 707-61-9.

A small-ring phosphacycle is found to catalyze the deoxygenative condensation of α-keto esters and carboxylic acids. The reaction provides a chemoselective catalytic synthesis of α-acyloxy ester products with good functional group compatibility. Based on both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV=O cycling. The importance of ring strain in the phosphacyclic catalyst is substantiated by an observed temperature-dependent product selectivity effect. The results point to an inherent distinction in design criteria for organophosphorus-based catalysts operating via PIII/PV=O redox cycling as opposed to Lewis base (nucleophilic) catalysis.

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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: 707-61-9, is researched, SMILESS is CC1=CP(CC1)(C2=CC=CC=C2)=O, Molecular C11H13OPJournal, Journal of Carbohydrate Chemistry called Novel synthesis and structures of amines and triazole-derived glycoside and nucleoside derivatives of phosphanyl sugar analogs, Author is Yamashita, Mitsuji; Suzuki, Kazumitsu; Kato, Yukihiro; Iida, Akihito; Ikai, Koichi; Reddy, Putta Mallikarjuna; Oshikawa, Tatsuo, the main research direction is triazole amino nucleoside phosphanyl analog preparation crystal structure; amino triazole glycoside phosphanyl analog preparation crystal structure.HPLC of Formula: 707-61-9.

3-Methyl-1-phenyl-2-phospholene and 1-phenyl-2-phospholene 1-oxides were converted into 2-bromo-3-hydroxy-3-methyl-1-phenylphospholane and 2-bromo-3-hydroxy-1-phenylphospholane 1-oxide (1-bromo-1,3,4-trideoxy-1,4-C-[(R, S)-phenylphosphinylidene]-glycero-tetrofuranose) by the action of bromine in aqueous medium. The bromo substituent of the phospholane was substituted by treatment with amines or an azide anion to afford novel glycoside derivatives of phosphanyl sugar analogs such as 2-amino-3-hydroxy-1-phenylphospholane (3,4-dideoxy-1,4-C-[(R, S)-phenylphosphinylidene]-glycero-tetrofuranosylamine) and 2-azido-3-hydroxy-3-methyl-1-phenylphospholane 1-oxides with retention of the configuration. The 1,3-dipolar cycloaddition of the 2-azido derivative of the phospholane with alkynes gave 3-hydroxy-3-methyl-1-phenyl-2-(triazol-1′-yl)phospholane 1-oxides as a novel triazole-derived nucleoside of phosphanyl sugar analogs. The structure of the glycoside and nucleoside derivatives of the phosphanyl sugar analogs prepared was determined from IR, NMR, and X-ray crystallog. anal.

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1,3-Benzodioxole – Wikipedia,
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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide( cas:707-61-9 ) is researched.Product Details of 707-61-9.O’Brien, Christopher J.; Nixon, Zachary S.; Holohan, Andrew J.; Kunkel, Stephen R.; Tellez, Jennifer L.; Doonan, Bryan J.; Coyle, Emma E.; Lavigne, Florie; Kang, Lauren J.; Przeworski, Katherine C. published the article 《Part I: The Development of the Catalytic Wittig Reaction》 about this compound( cas:707-61-9 ) in Chemistry – A European Journal. Keywords: Wittig reaction phosphole phospholane phosphate oxide preparation catalyst; Wittig reaction; alkenes; homogeneous catalysis; olefination; organocatalysis. Let’s learn more about this compound (cas:707-61-9).

The authors have developed the first catalytic (in phosphane) Wittig reaction (CWR). The utilization of an organosilane was pivotal for success as it allowed for the chemoselective reduction of a phosphane oxide. Protocol optimization evaluated the phosphane oxide pre-catalyst structure, loading, organosilane, temperature, solvent, and base. These studies demonstrated that to maintain viable catalytic performance it was necessary to employ cyclic phosphane oxide pre-catalysts of type 1. Initial substrate studies utilized sodium carbonate as a base, and further experimentation identified N,N-diisopropylethylamine (DIPEA) as a soluble alternative. The use of DIPEA improved the ease of use, broadened the substrate scope and decreased the pre-catalyst loading. The optimized protocols were compatible with alkyl, aryl, and heterocyclic (furyl, indolyl, pyridyl, pyrrolyl, and thienyl) aldehydes to produce both disubstituted and trisubstituted olefins in moderate-to-high yields (60-96%) by using a pre-catalyst loading of 4-10 mol%. Kinetic E/Z selectivity was generally 66:34. Complete (E)-selectivity for disubstituted α,β-unsaturated products was achieved through a phosphane-mediated isomerization event. The CWR was applied to the synthesis of a known precursor to the anti-Alzheimer drug donepezil hydrochloride, on a multi-gram scale (12.2 g, 74% yield). In addition, the described CWR is the only transition-metal-free/heavy-metal-free catalytic olefination process, excluding proton-catalyzed elimination reactions. The synthesis of the target compounds was achieved (1R,3S)-rel-3-methyl-1-phenylphospholane 1-oxide, (1R,3R)-rel-3-methyl-1-phenylphospholane 1-oxide, 1-phenylphospholane 1-oxide as catalyst precursors. 2-Phenyl-1,3,2-dioxaphospholane 2-oxide, diethylphenylphosphine oxide, 5-phenyl-5H-benzo[b]phosphindole 5-oxide, (2R,2’R,5R,5’R)-1,1′-(1,2-ethanediyl)bis[2,5-bis(1-methylethyl)phospholane], 2-[2-[(2R,5R)-2,5-dimethyl-1-phospholanyl]phenyl]-1,3-dioxolane were also evaluated.

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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: 707-61-9, is researched, SMILESS is CC1=CP(CC1)(C2=CC=CC=C2)=O, Molecular C11H13OPJournal, Tetrahedron Letters called An efficient approach towards the stereospecific synthesis of epoxides from phospholene oxides, Author is Yamashita, Mitsuji; Krishna Reddy, Valluru; Rao, Lakonda Nagaprasada; Haritha, Buchammagari; Maeda, Motoki; Suzuki, Keiji; Totsuka, Hirono; Takahashi, Masaki; Oshikawa, Tatsuo, the main research direction is stereospecific synthesis epoxide phospholene oxide; stereoselective synthesis epoxide phospholene oxaphosphabicyclohexane oxide; epoxy phospholane oxide preparation stereoselective oxidation sodium peroxide phosphole; epoxyphosphole oxide preparation stereoselective oxidation sodium peroxide phosphole; AZT analog oxaphosphabicyclohexane oxide intermediate preparation oxidation; diastereoselective synthesis epoxide phospholene oxaphosphabicyclohexane oxide.Safety of 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide.

A novel method has been developed for stereospecific conversion of 2-phospholene 1-oxides into their corresponding 2,3-epoxides in high yields using sodium peroxide as a reagent. 2,3-Dihydro-1-phenyl-1H-phosphole 1-oxide (I) was inert to oxidation with 3-chloroperbenzoic acid; oxidation of I with bromine or N-bromoacetamide gave 2-bromo-3-hydroxy-1-phenylphospholane oxide as diastereomeric mixture and subsequent treatment of the bromohydrin gave a mixture of (1R,2S,5S)-rel-2-phenyl-6-Oxa-2-phosphabicyclo[3.1.0]hexane 2-oxide (erythro, II) and (1R,2R,5S)-rel-2-phenyl-6-Oxa-2-phosphabicyclo[3.1.0]hexane 2-oxide (threo). Epoxidation of I using sodium peroxide [Na2(O2)] gave II as a single diastereomer in 76% yield. 2,3-Dihydro-4-methyl-1-phenyl-1H-phosphole 1-oxide and 2,3-dihydro-1-methoxy-4-methyl-1H-phosphole 1-oxide failed to react with sodium peroxide [Na2(O2)]. The compounds thus prepared are intermediates for AZT analogs of phospha sugars (no data).

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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 Recycling the Waste: The Development of a Catalytic Wittig Reaction. Author is O’Brien, Christopher J.; Tellez, Jennifer L.; Nixon, Zachary S.; Kang, Lauren J.; Carter, Andra L.; Kunkel, Stephen R.; Przeworski, Katherine C.; Chass, Gregory A..

The first Wittig reaction catalytic in phosphine has been developed. A variety of heteroaryl, aryl, and alkyl aldehydes could be efficiently converted to the corresponding alkenes in moderate to high yield with the utilization of the phosphine oxide precatalyst I.

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