N-methoxycarbonyl N-methyl L-phenylalanine benzyl ester | 552314-30-4

• 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: N-methoxycarbonyl N-methyl L-phenylalanine benzyl ester
• 英文别名: N-(Methoxycarbonyl)-N-methyl-L-phenylalanine phenylmethyl ester；benzyl (2S)-2-[methoxycarbonyl(methyl)amino]-3-phenylpropanoate
• CAS: 552314-30-4
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: APZXKEZOHLWRBG-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 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：

  醋酸叔丁酯 、 N-methoxycarbonyl N-methyl L-phenylalanine benzyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 生成 (S)-4-(Methoxycarbonyl-methyl-amino)-3-oxo-5-phenyl-pentanoic acid tert-butyl ester 、 3-Hydroxy-3-[(S)-1-(methoxycarbonyl-methyl-amino)-2-phenyl-ethyl]-pentanedioic acid di-tert-butyl ester
  参考文献：
  名称：

  An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives

  摘要：

  Cross-ester condensation between N-protected amino acid ester and the lithium enolate prepared from alkyl acetate gave the corresponding beta-ketoester in high yield without the formation of the tertiary alcohol that is commonly seen as by-product. This interesting reaction is applicable to the amino acid derivatives with suitable N-protecting groups, which can help to stabilize the reaction intermediates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00464-7

文献信息

• An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives
  作者：Yutaka Honda、Satoshi Katayama、Mitsuhiko Kojima、Takayuki Suzuki、Kunisuke Izawa

  DOI：10.1016/s0040-4039(03)00464-7

  日期：2003.4

  Cross-ester condensation between N-protected amino acid ester and the lithium enolate prepared from alkyl acetate gave the corresponding beta-ketoester in high yield without the formation of the tertiary alcohol that is commonly seen as by-product. This interesting reaction is applicable to the amino acid derivatives with suitable N-protecting groups, which can help to stabilize the reaction intermediates. (C) 2003 Elsevier Science Ltd. All rights reserved.