119244-19-8

Basic information

• Product Name: 4-Pentenoic acid, 2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2R)-
• CAS NO: 119244-19-8
• Molecular Formula: C22H25NO2
• Molecular Weight: 335.446
• Mol File: 119244-19-8.mol
• Article Data: 82

Chemical Properties

• CAS DataBase Reference: 4-Pentenoic acid, 2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentenoic acid, 2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2R)-(119244-19-8)
• EPA Substance Registry System: 4-Pentenoic acid, 2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2R)-(119244-19-8)

Safety Data

• Hazardous Substances Data: 119244-19-8(Hazardous Substances Data)

Upstream product

• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 70122-89-3 tert-butyl allyl carbonate 
• 591-87-7 Allyl acetate 
• 27532-96-3 glycine tert-butyl ester hydrochloride 
• 1013-88-3 Benzophenone imine 
• 556-56-9 allyl iodid 
• 106-95-6 allyl bromide 

Downstream Products

• 163210-82-0 (S)-2-allylglycine tert-butyl ester 
• 611182-70-8 TIPSO-D-Hpla(TIPS)-D-Leu-L-Choi(TIPS)-L-Arg(δ,ω'-di-Cbz)-OMe 
• 611182-71-9 TIPSO-D-Hpla(TIPS)-D-Leu-L-Choi(TIPS)-L-Argol(δ,ω'-di-Cbz) 
• 611182-68-4 Boc-L-Choi(TIPS)-L-Arg(δ,ω'-di-Cbz)-OMe 
• 611182-69-5 C₄₁H₆₁N₅O₈Si 
• 611182-67-3 C₃₇H₄₉N₅O₁₀ 
• 139033-70-8 L-Arg(δ,ω'-di-Cbz)-OMe 
• 89985-87-5 methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate 
• 95198-94-0 C₁₁H₂₀NO₄CN₃H₂(C₈H₇O₂)2 
• 139033-70-8 C₂₃H₂₈N₄O₆ 
• 701914-23-0 C₂₃H₂₈N₄O₆ 
• 150652-96-3 (R)-2-(tert-butoxycarbonyl)amino-4-pentenoic acid methyl ester 
• 50299-15-5 methyl (S)-allylglycinate 

Relevant articles and documents

Cyclopeptoids as phase-transfer catalysts for the enantioselective synthesis of α-amino acids

The first application of cyclopeptoids in asymmetric phasetransfer catalysis was examined. A small library of nine alternating N-substituted-glycine and proline hexacyclopeptoids was tested in the enantioselective alkylation of N-(diphenyl-methylene)glyci

A New Active Catalyst Species for Enantioselective Alkylation by Phase-Transfer Catalysis

This paper briefly reviews the use of Schiff base substrates in amino acid synthesis.Recent studies lead to the proposal of a new active catalyst species (12) for the asymmetric PTC alkylation of active methylene compounds (2).Mechanistic implications are

Heterogeneous simplified Maruoka phase-transfer catalyst tethered on poly(styrene-co-acrylamide) microsphere: Structure-activity relationship in enantioselective Α-alkylation

The covalent immobilization of valuable simplified Maruoka catalyst onto poly(styrene-co-acrylamide)microsphere at different locations was developed for the first time through the copolymerization of Maruoka catalyst-functionalized styrene with styrene an

The asymmetric alkylation reaction of glycine derivatives catalyzed by the novel chiral phase transfer catalysts

Herein a new series of chiral phase transfer catalysts derived from the cinchona alkaloids were synthesized and applied in the asymmetric alkylation of glycine derivatives with high yields and moderate to excellent ee values (39.5-99.7%).

A new class of acetophenone-based cinchona alkaloids as phase-transfer catalysts: Application to the enantioselective synthesis of α-amino acids

A new class of acetophenone-based cinchona alkaloid-de-rived quaternary ammonium salts were prepared and evaluated as phase-transfer catalysts in the enantioselective alkylation of glycine imine ester. +R 3N-CH2COAr and el

Synthesis and application of dimeric Cinchona alkaloid phase-transfer catalysts: α,α′-bis[O(9)-allylcinchonidinium]-o, m, or p-xylene dibromide

A dimeric Cinchona alkaloid ammonium salt, α,α′-bis[O(9)-allylcinchonidinium]-m-xylene dibromide 4, has been developed as a new efficient phase-transfer catalyst; the catalytic enantioselective alkylation of N-(diphenylmethylene)glycine tert-butyl ester u

Contrast performance in catalytic ability - New cinchona phase transfer catalysts for asymmetric synthesis of α-amino acids

Two new cinchona phase transfer catalysts are prepared from dihydrocinchonidine using 13-picenylmethyl bromide and 1-pyrenylmethyl bromide, respectively. A total contrast in catalytic efficiency is observed during the asymmetric alkylation of glycinate es

Studies on the enantioselective synthesis of α-amino acids via asymmetric phase-transfer catalysis

In this paper, we describe investigations into the use of cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts for the asymmetric alkylation of a benzophenone-derived glycine-imine. Utility of this process is demonstrated by the enantioselective synthesis of a range of α-amino acid esters.

Dramatic rate enhancement of asymmetric phase-transfer-catalyzed alkylations

The intervention of crown ethers or achiral quaternary ammonium salts as achiral phase-transfer catalysts (PTCs, see scheme) in a chiral PTC system leads to dramatic rate enhancements in the asymmetric alkylation of glycine derivatives.

Powerful chiral phase-transfer catalysts for the asymmetric synthesis of α-alkyl- and α,α-dialkyl-α-amino acids

The catalytic performance of the chiral phase-transfer catalyst 1 (0.1-0.01 mol%) in the asymmetric alkylation of protected glycine and alanine derivatives exceeds that of existing catalysts. The reaction is used in the enantioselective synthesis of struc

An unusual electronic effect of an aromatic-F in phase-transfer catalysts derived from cinchona-alkaloid.

[structure: see text] Various N-benzylcinchonidinium salts were prepared to study electronic factors in the catalytic enantioselective phase-transfer alkylation of glycine anion equivalent. An ortho-fluoro substituent on the benzyl group in the quaternary

Effects of aromatic substituents on binaphthyl-based chiral spiro-type ammonium salts in asymmetric phase-transfer reactions

Spiro-type phase-transfer catalysts prepared from two equivalents of a single binaphthyl subunit were designed and applied to the asymmetric alkylation and direct aldol reactions of a glycine derivative. The effects of the substitution pattern of the bina

The counterion effect in the phase-transfer catalyzed asymmetric synthesis of α-amino acids promoted by anthryl-derived dimeric Cinchona ammonium salts

Dimeric ammonium salts derived from cinchonidine or cinchonine and a bridging (anthracen-9,10-yl)dimethyl moiety bearing different counter-anions are used as chiral phase-transfer catalysts in the asymmetric alkylation reaction of a benzophenone-imine ter

Synthesis of new dimeric-PEG-supported cinchona ammonium salts as chiral phase transfer catalysts for the alkylation of Schiff bases with water as the solvent

The water-soluble PEG-supported cinchona ammonium salts were successfully synthesized and used as chiral phase transfer catalysts for the asymmetric alkylation of tert-butyl benzophenone Schiff base derivatives with high chemical yields (up to 98%) and en

Evidence of the electronic factor for the highly enantioselective catalytic efficiency of Cinchona-derived phase-transfer catalysts

(Chemical Equation Presented) The Cinchona alkaloid-derived quaternary ammonium salts containing 2′-N-oxypyridine and 2′-cyanobenzene moieties were prepared and evaluated as phase-transfer catalysts in the enantioselective alkylation of glycine imine este

Highly efficient polymer supported phase-transfer catalysts containing hydrogen bond inducing functional groups

Merrifield resin supported cinchona ammonium salts bearing 2′-fluorobenzene, 2′-cyanobenzene and 2′-N-oxypyridine groups were prepared and applied to the phase-transfer catalytic alkylation of N-(diphenylmethylene)glycine tert-butyl ester for the enantios

Facile one-pot fabrication of a silica gel-supported chiral phase-transfer catalyst - N-(2-cyanobenzyl)-O(9)-allyl-cinchonidinium salt

A novel type of silica gel-supported cinchona alkaloid-based quaternary ammonium salt was prepared by available one-pot synthesis for the first time through the free radical addition of the sulfhydryl group of 3-mercaptopropyltrimethoxysilane to an exocyc

Symmetrical 4,4′,6,6′-tetraarylbinaphthyl-substituted ammonium bromide as a new, chiral phase-transfer catalyst

Binaphthyl-modified spiro-type symmetrical phase-transfer catalysts possessing 4,4′,6,6′-tetraaryl substituents are shown to exhibit high asymmetric induction in asymmetric alkylation of benzophenone imine glycine tert-butyl ester under ordinary phase-tra

An efficient homogeneous catalytic enantioselective synthesis of α- amino acid derivatives

The catalytic enantioselective alkylation of the benzophenone imine of glycine t-butyl ester is realized by an efficient homogeneous reaction with alkyl halides, the neutral, non-ionic phosphazene base (BEMP or BTPP), and chiral quaternary ammonium salts

Synergistic Cu/Pd Catalysis for Enantioselective Allylation of Ketimine Esters: The Direct Synthesis of α-Substituted α-Amino Acids and 2H-Pyrrols

An efficient synergistic Cu/Pd catalyzed enantioselective α-allylation of acyclic ketimine esters has been reported, which provides an entry to nonproteinogenic α-allyl α-amino acids in high yield, exclusive regioselectivity, and excellent enantioselectivity. Moreover, the more challenging cyclic ketimine ester could also be employed as a nucleophile for the construction of 3,4-dihydro-2H-pyrrole derivatives bearing a quaternary stereogenic center using the same catalytic system. (Figure presented.).

Counter-rotatable dual cinchona quinuclidinium salts and their phase transfer catalysis in enantioselective alkylation of glycine imines

Dual cinchona quinuclidinium salts with a diphenyl ether linker were synthesized and used as powerful asymmetric phase transfer catalysts in the α-alkylation of imines of glycine and alanine ester with 0.01-0.1 mol% loading (17 examples, 92-99% ee). Skewed conformers of dual quinuclidiniums at TS were proposed to rationalize their high efficiencyviaDFT calculations.

Improved access to chiral tetranaphthoazepinium-based organocatalysts using aqueous ammonia as nitrogen source

The class of 3,30-diaryl substituted tetranaphthobisazepinium bromides has found wide application as highly efficient C2-symmetrical phase-transfer catalysts (PTCs, Maruoka type catalysts). Unfortunately, the synthesis requires a lar