(S)-2-[(2-Chloro-acetyl)-(4-methoxy-phenyl)-amino]-3-phenyl-propionic acid methyl ester | 909713-23-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-[(2-Chloro-acetyl)-(4-methoxy-phenyl)-amino]-3-phenyl-propionic acid methyl ester
• 英文别名: methyl (2S)-2-(N-(2-chloroacetyl)-4-methoxyanilino)-3-phenylpropanoate
• CAS: 909713-23-1
• 化学式: C₁₉H₂₀ClNO₄
• 分子量: 361.825
• InChiKey: GIOHDFCJMLPYCP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-[(2-Chloro-acetyl)-(4-methoxy-phenyl)-amino]-3-phenyl-propionic acid methyl ester 在 (4R,5R)-2,2-二甲基-a,a,a',a'-四苯基-1,3-二氧戊环-4,5-二甲醇 、 (叔丁基亚氨基)三(吡咯烷)膦 作用下， 以 乙腈 为溶剂， 生成 (4R)-4-benzyl-4-methoxycarbonyl-1-(p-methoxy)phenyl-2-azetidinone 、 (4S)-4-benzyl-4-methoxycarbonyl-1-(p-methoxy)phenyl-2-azetidinone
  参考文献：
  名称：

  β-Lactams derived from phenylalanine and homologues: effects of the distance between the aromatic rings and the α-stereogenic reactive center on the memory of chirality

  摘要：

  The enantioselectivity in the base-promoted cyclization of N-chloroacetyl derivatives of Phe, Phg, and Hph is dependent on the side-chain length, with the best results for Phg analogues (up to 74% ee). In contrast, shortening of the N-substituent, from a (p-methoxy)benzyl group to a (p-methoxy)phenyl moiety, led to a decrease in selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.057
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 在 copper diacetate 、 TEA 、 methyloxirane 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-2-[(2-Chloro-acetyl)-(4-methoxy-phenyl)-amino]-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  β-Lactams derived from phenylalanine and homologues: effects of the distance between the aromatic rings and the α-stereogenic reactive center on the memory of chirality

  摘要：

  The enantioselectivity in the base-promoted cyclization of N-chloroacetyl derivatives of Phe, Phg, and Hph is dependent on the side-chain length, with the best results for Phg analogues (up to 74% ee). In contrast, shortening of the N-substituent, from a (p-methoxy)benzyl group to a (p-methoxy)phenyl moiety, led to a decrease in selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.057