methyl (2R)-2-[(4-methoxyphenyl)methylamino]-2-phenylacetate | 909713-15-1

• 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: methyl (2R)-2-[(4-methoxyphenyl)methylamino]-2-phenylacetate
• CAS: 909713-15-1
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: XKEIQSCGXGOULH-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-[(4-methoxyphenyl)methylamino]-2-phenylacetate 在 (叔丁基亚氨基)三(吡咯烷)膦 、 methyloxirane 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (4S)-1-(p-methoxy)benzyl-4-phenyl-4-methoxycabronyl-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：

  (R)-氨基苯乙酸甲酯 、 4-甲氧基苯甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 methyl (2R)-2-[(4-methoxyphenyl)methylamino]-2-phenylacetate
  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

文献信息

• 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
  作者：M. Angeles Bonache、Carlos Cativiela、M. Teresa García-López、Rosario González-Muñiz

  DOI：10.1016/j.tetlet.2006.06.057

  日期：2006.8

  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.