110212-61-8

Basic information

• Product Name: (Isopropyloxycarbonylmethylene)triphenylphosphorane
• Synonyms: (Isopropyloxycarbonylmethylene)triphenylphosphorane
• CAS NO: 110212-61-8
• Molecular Formula: C₂₃H₂₃O₂P
• Molecular Weight: 362.401281
• Mol File: 110212-61-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Isopropyloxycarbonylmethylene)triphenylphosphorane(CAS DataBase Reference)
• NIST Chemistry Reference: (Isopropyloxycarbonylmethylene)triphenylphosphorane(110212-61-8)
• EPA Substance Registry System: (Isopropyloxycarbonylmethylene)triphenylphosphorane(110212-61-8)

Safety Data

• Hazardous Substances Data: 110212-61-8(Hazardous Substances Data)

Usage

Description

(Isopropyloxycarbonylmethylene)triphenylphosphorane, with the chemical formula (CH3)2CHOCOCH(CO2C6H5)3, is a phosphorane derivative utilized as a reagent in organic synthesis. (Isopropyloxycarbonylmethylene)triphenylphosphorane is a strong base and is renowned for its high reactivity and selectivity in converting aldehydes and ketones into alkenes through the formation of stable ylides.

Uses

Used in Pharmaceutical Industry:
(Isopropyloxycarbonylmethylene)triphenylphosphorane is used as a reagent for the synthesis of various organic compounds, playing a crucial role in the development of new pharmaceuticals. Its ability to efficiently convert aldehydes and ketones into alkenes makes it a valuable tool in the creation of complex molecular structures, which are often found in many drugs.
Used in Agrochemical Industry:
In the agrochemical industry, (Isopropyloxycarbonylmethylene)triphenylphosphorane is employed as a reagent for the synthesis of organic compounds used in the development of pesticides, herbicides, and other agricultural chemicals. Its high reactivity and selectivity are essential in creating specific molecules that can target and control pests and weeds effectively.
Used in Organic Synthesis:
(Isopropyloxycarbonylmethylene)triphenylphosphorane is used as a reagent in the formation of Wittig reagents, which are essential in organic synthesis for creating a wide range of carbon-carbon double bond-containing compounds. This application is vital in the production of various chemicals, materials, and pharmaceuticals that require specific structural features.

Upstream product

• 159377-42-1 (isopropyloxycarbonylmethyl)triphenylphosphonium bromide 
• 952609-88-0 [(isopropoxycarbonyl)(phenylcarbamoyl)methylene]triphenylphosphorane 
• 29921-57-1 isopropyl 2-bromoacetate 
• 603-35-0 triphenylphosphine 
• 105-48-6 isopropyl chloroacetate 

Downstream Products

• 100-42-5 styrene 
• 7283-70-7 diisopropyl fumarate 
• 10099-70-4 diisopropyl maleate 
• 3878-45-3 triphenylphosphine sulfide 
• 952609-88-0 [(isopropoxycarbonyl)(phenylcarbamoyl)methylene]triphenylphosphorane 
• 1147279-72-8 ethyl isopropyl 2-(triphenylphosphoranylidene)malonate 
• 1147279-69-3 methyl isopropyl 2-(triphenylphosphoranylidene)malonate 
• 1219135-95-1 (Z)-isopropyl 3-((2R,3R,4S,5R)-3-benzyloxy-4-hydroxy-5-(nitromethyl)tetrahydrofuran-2-yl)acrylate 
• 1315576-40-9 (5S,9R)-isopropyl 1,3-dibenzyl-9-(4-(benzyloxy)butyl)-2,4-dioxo-1,3-diazaspiro[4.4]non-7-ene-7-carboxylate 
• 1315576-41-0 (5S,9R)-isopropyl 1,3-dibenzyl-9-(3-methoxy-3-oxopropyl)-2,4-dioxo-1,3-diazaspiro[4.4]non-7-ene-7-carboxylate 
• 1315576-42-1 (5S,9R)-isopropyl 1,3-dibenzyl-9-(4-(1,3-dioxoisoindolin-2-yl)butyl)-2,4-dioxo-1,3-diazaspiro[4.4]non-7-ene-7-carboxylate 
• 1315575-92-8 (5R,9S)-isopropyl 1,3-dibenzyl-9-(4-(benzyloxy)butyl)-2,4-dioxo-1,3-diazaspiro[4.4]non-7-ene-7-carboxylate 
• 1315575-93-9 (5R,9S)-isopropyl 1,3-dibenzyl-9-(3-methoxy-3-oxopropyl)-2,4-dioxo-1,3-diazaspiro[4.4]non-7-ene-7-carboxylate 
• 1315575-94-0 (5R,9S)-isopropyl 1,3-dibenzyl-9-(4-(1,3-dioxoisoindolin-2-yl)butyl)-2,4-dioxo-1,3-diazaspiro[4.4]non-7-ene-7-carboxylate 

Relevant articles and documents

Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones

An efficient enantioselective [3+2] cycloaddition of isomünchnones with methyleneindolinones that are generated by anin situintramolecular addition of the carbonyl group to rhodium carbenes is realized with a chiralN,N′-dioxide/Zn(ii) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values.

Heavier Carbonyl Olefination: The Sila-Wittig Reaction

The Wittig reaction is one of the most versatile tools in the repertoire of organic chemists. Thus, a broad variety of carbonyl compounds can be converted to tailor-made alkenes with phosphorus ylides under mild conditions. However, no comparable reaction has been reported for silanones, the silicon congeners of ketones. Here, we demonstrate for the first time the successful application of the Wittig olefination to iminosilylsilanone 1. The selective formation of a series of silenes (R2Sia? CR2) via the sila-Wittig reaction revealed an unprecedented approach to otherwise elusive compounds. In addition, the highly reactive and zwitterionic nature of 1 was also susceptible to nucleophilic attacks and cycloaddition reactions by and with the phosphorus ylides. Our results therefore make another important contribution to discovering the differences and similarities between carbon and silicon.

Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons

A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.