methyl (S)-2-cyano-2-methyl-3-phenylpropanoate | 27771-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (S)-2-cyano-2-methyl-3-phenylpropanoate
• 英文别名: (+)-Methyl-2-cyan-2-methyl-3-phenylpropionat；methyl (2S)-2-cyano-2-methyl-3-phenylpropanoate
• CAS: 27771-06-8
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: CTHXWTHXNBGTQO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-cyano-2-methyl-3-phenylpropanoate 在 镍 氨 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (S)-α-benzyl-α-methyl-β-alanine methyl ester
  参考文献：
  名称：

  Efficient enantioconvergent synthesis of (S)-α-benzyl-α-methyl-β-alanine from (R)- and (S)-2-cyano-2-methyl-3-phenylpropanoic acid

  摘要：

  An efficient synthesis of (S)-alpha-benzyl-alpha-methyl-beta-alanine in 59% overall yield from benzaldehyde and methyl cyanoacetate has been developed. Enantioconvergent approaches to the synthesis of the target alpha,alpha-disubstituted beta-amino acid from both enantiomers of previously resolved 2-eyano-2-methyl-3-phenylpropanoic acid constitute the key steps in the proposed methodology. The use of inexpensive and readily available reagents and the simplicity of the experimental procedures make the present protocol synthetically attractive and of great potential for scale up. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00443-9
• 作为产物：
  描述：

  (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (S)-2-cyano-2-methyl-3-phenylpropanoate 在 N-甲基吗啉 、 氢氧化钾 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 methyl (S)-2-cyano-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  First asymmetric synthesis of an acyclic β,β-dialkylated-γ-aminobutyric acid

  摘要：

  Enantiomerically pure (R)-gamma-amino-beta-benzyl-beta-methylbutyric acid, an acyclic beta,beta-dialkyl GABA derivative, is efficiently synthesised from (1S,2R,4R)-10-dicyclohexylsulfamoylisobomyl 2-cyanopropanoate by a sequence based on benzylation, Arndt-Eistert homologation and nitrile reduction. Benzylation of (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using potassium carbonate under not strictly anhydrous conditions occurs diastereoselectively to afford (1S,2R,4R)-10-dicyclohexylsulfamoylisobomyl (S)-2-cyano-2methyl-3-phenylpropanoate, the key chiral intermediate from which the desired gamma-amino acid is obtained in five steps in 65% overall yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.021

文献信息

• Catalytic asymmetric alkylation of α-cyanocarboxylates and acetoacetates using a phase-transfer catalyst
  作者：Kazuhiro Nagata、Daisuke Sano、Yu Shimizu、Michiko Miyazaki、Takuya Kanemitsu、Takashi Itoh

  DOI：10.1016/j.tetasy.2009.10.018

  日期：2009.11

  The catalytic asymmetric alkylation of alpha-cyanocarboxylates and acetoacetates with an alkyl halide was performed under phase-transfer conditions to afford compounds which have a chiral quaternary carbon with up to 97% and 94% ee, respectively. As applications of this method, chiral 2-oxindole derivatives and a beta-lactam derivative were synthesized. (C) 2009 Elsevier Ltd. All rights reserved.
• Terashima,S. et al., Chemical and pharmaceutical bulletin, 1969, vol. 17, p. 2533 - 2539
  作者：Terashima,S. et al.

  DOI：——

  日期：——