(2Z)-(+)-methyl 2-methyl-3-[(S)-α-methylbenzylamino]-2-butenoate | 428454-82-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2Z)-(+)-methyl 2-methyl-3-[(S)-α-methylbenzylamino]-2-butenoate
• 英文别名: methyl (Z)-2-methyl-3-[[(1S)-1-phenylethyl]amino]but-2-enoate
• CAS: 428454-82-4
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: CQGFFOLNIFZJTI-WEHUKYGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z)-(+)-methyl 2-methyl-3-[(S)-α-methylbenzylamino]-2-butenoate 在 溶剂黄146 、 对苯二酚 作用下， 以 四氢呋喃 为溶剂， 反应 74.0h， 生成 (S,S)-2-acetyl-4-acetylamino-2-methyl-pentanedioic acid dimethyl ester
  参考文献：
  名称：

  Asymmetric Michael reaction between a chiral α,β-dimethyl-β-enamino ester and α-substituted acrylates

  摘要：

  An asymmetric Michael reaction between a chiral alpha,beta-dimethyl-beta-enamino ester derived from (S)-1-phenylethylamine and alpha-substituted acrylates is reported. Methyl acetamidoacrylate and methyl acetoxyacrylate furnished the expected Michael adduct with good ee's and de's. By contrast, an annulation process of the intermediary imine took place when using methyl methacrylates. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.028
• 作为产物：
  描述：

  2-甲基-3-氧代丁酸甲酯 、 (S)-(-)- α-甲基苄胺 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以90.6%的产率得到(2Z)-(+)-methyl 2-methyl-3-[(S)-α-methylbenzylamino]-2-butenoate
  参考文献：
  名称：

  Maiti; Ghoshal; Mukhopadhyay, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1072 - 1080

  摘要：

  DOI：

文献信息

• Maiti; Ghoshal; Mukhopadhyay, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1072 - 1080
  作者：Maiti、Ghoshal、Mukhopadhyay、Achari、Banerjee

  DOI：——

  日期：——
• The asymmetric Michael-type alkylation of chiral β-enamino esters: critical role of a benzyl ester group in the racemization of adducts
  作者：Mathieu Pizzonero、Frédéric Hendra、Sandrine Delarue-Cochin、Marie-Elise Tran Huu-Dau、Françoise Dumas、Christian Cavé、Mohammed Nour、Jean d’Angelo

  DOI：10.1016/j.tetasy.2005.10.034

  日期：2005.11

  In contrast with keto diester (R)-10a bearing a methyl ester group at the quaternary carbon center, the benzyl ester analogue (R)-10a partially racemized during workup, thereby revealing that the nature of the ester group at the quaternary carbon center has a critical role in the rate of racemization of such Michael adducts. (c) 2005 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of glutamate derivatives
  作者：Rokhayatou Seck、Abdoulaye Gassama、Mohammed Nour、Luc Demange、Christian Cavé

  DOI：10.24820/ark.5550190.p009.974

  日期：——
• 10.3998/ark.5550190.0018.400
  作者：Seck, Rokhayatou、Gassama, Abdoulaye、Nour, Mohammed、Demange, Luc、Cavé, Christian

  DOI：10.3998/ark.5550190.0018.400

  日期：——
• Asymmetric Michael reaction between a chiral α,β-dimethyl-β-enamino ester and α-substituted acrylates
  作者：Frédéric Hendra、Mohammed Nour、Isabelle Baglin、Georges Morgant、Christian Cavé

  DOI：10.1016/j.tetasy.2004.01.028

  日期：2004.3

  An asymmetric Michael reaction between a chiral alpha,beta-dimethyl-beta-enamino ester derived from (S)-1-phenylethylamine and alpha-substituted acrylates is reported. Methyl acetamidoacrylate and methyl acetoxyacrylate furnished the expected Michael adduct with good ee's and de's. By contrast, an annulation process of the intermediary imine took place when using methyl methacrylates. (C) 2004 Elsevier Ltd. All rights reserved.