2605-67-6 Usage
Description
Methyl (triphenylphosphoranylidene)acetate, also known as (Methoxycarbonylmethylene)triphenylphosphorane, is a white to off-white powder that serves as a versatile reagent in organic chemistry. It is primarily used in olefination reactions and is known for its role as a Wittig reagent, facilitating the two-carbon homologation of aldehydes to α,β-unsaturated esters.
Uses
Used in Olefination Reactions:
Methyl (triphenylphosphoranylidene)acetate is used as a reagent for olefination reactions, specifically in the Wittig reaction with aldehydes to give substituted methyl acrylates. This reaction is crucial for the synthesis of various organic compounds, including α,β-unsaturated esters.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl (triphenylphosphoranylidene)acetate is used as a key intermediate in the synthesis of various drugs and drug candidates. Its ability to form α,β-unsaturated esters makes it a valuable tool in the development of new pharmaceutical compounds.
Used in Organic Synthesis:
Methyl (triphenylphosphoranylidene)acetate is used as a reagent in the efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine. This application highlights its versatility in organic synthesis and its potential in creating complex molecular structures.
Used in the Preparation of (Triphenylphosphoranylidene)-Ketene:
Methyl (triphenylphosphoranylidene)acetate is also used in the preparation of (triphenylphosphoranylidene)-ketene, which is an important intermediate in the synthesis of various organic compounds.
Used in Academic Research:
In academic research, Methyl (triphenylphosphoranylidene)acetate is utilized in the Wittig reaction to produce methyl (2E)-3-(2-nitrophenyl) acrylate with a triphenylphosphine oxide side product. This reaction takes place in a silica gel matrix to ensure even product dispersion for chromatography, making it a valuable tool for teaching and research purposes in organic chemistry.
Purification Methods
Crystallise it by dissolving in it AcOH and adding pet ether (b 40-50o) to give colourless plates. UV max (A 1mm ): 222nm (865) and 268nm (116) [Isler et al. Helv Chim Acta 40 1242 1957]. [Beilstein 16 IV 977.]
Check Digit Verification of cas no
The CAS Registry Mumber 2605-67-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,0 and 5 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2605-67:
(6*2)+(5*6)+(4*0)+(3*5)+(2*6)+(1*7)=76
76 % 10 = 6
So 2605-67-6 is a valid CAS Registry Number.
InChI:InChI=1/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3
2605-67-6Relevant articles and documents
Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates
Liu, Teng,He, Chixian,Wang, Fan,Shen, Xiang,Li, Yongqin,Lang, Man,Li, Guijun,Huang, Chao,Cheng, Feixiang
, p. 518 - 526 (2020/10/12)
A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E -selectivity.
Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.
supporting information, p. 9413 - 9418 (2021/12/09)
β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.
TREATMENT OF DISORDERS ASSOCIATED WITH OXIDATIVE STRESS AND COMPOUNDS FOR SAME
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Page/Page column 51-52, (2021/09/17)
The present invention relates to the treatment of disorders associated with oxidative stress including neuropathic pain and small synthetically derived compounds for treating such disorders.
