N-[(2S)-2-(benzylamino)-4-oxo-4-phenylbutanoyl]-L-leucine | 1269627-60-2

• 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-[(2S)-2-(benzylamino)-4-oxo-4-phenylbutanoyl]-L-leucine
• 英文别名: (2S)-2-[[(2S)-2-(benzylamino)-4-oxo-4-phenylbutanoyl]amino]-4-methylpentanoic acid
• CAS: 1269627-60-2
• 化学式: C₂₃H₂₈N₂O₄
• 分子量: 396.486
• InChiKey: GEZVAJNNEPTXKE-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(2S)-2-(benzylamino)-4-oxo-4-phenylbutanoyl]-L-leucine 在 盐酸 、 硫酸 、 palladium on carbon 、 水 、 氢溴酸 、 氢气 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 20.0~50.0 ℃ 、111.47 kPa 条件下， 反应 287.0h， 生成 N-[(2R)-2-amino-4-(4-methoxyphenyl)butanoyl]-L-leucine
  参考文献：
  名称：

  Crystallisation-induced asymmetric transformation (CIAT) for the synthesis of dipeptides containing homophenylalanine

  摘要：

  A novel synthesis of highly enantioenriched dipeptides containing homophenylalanine is described. The process involves a crystallisation-induced asymmetric transformation (CIAT) in a Michael addition followed by exhaustive reduction. A unique example of a formally stereodivergent CIAT in conjugate addition of an achiral N-nucleophile to enantiomerically pure Michael acceptor has been discovered. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.015
• 作为产物：
  描述：

  反式-3-苯甲酰丙烯酸 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 97.0h， 生成 N-[(2S)-2-(benzylamino)-4-oxo-4-phenylbutanoyl]-L-leucine
  参考文献：
  名称：

  Crystallisation-induced asymmetric transformation (CIAT) for the synthesis of dipeptides containing homophenylalanine

  摘要：

  A novel synthesis of highly enantioenriched dipeptides containing homophenylalanine is described. The process involves a crystallisation-induced asymmetric transformation (CIAT) in a Michael addition followed by exhaustive reduction. A unique example of a formally stereodivergent CIAT in conjugate addition of an achiral N-nucleophile to enantiomerically pure Michael acceptor has been discovered. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.015

文献信息

• Crystallisation-induced asymmetric transformation (CIAT) for the synthesis of dipeptides containing homophenylalanine
  作者：Pavol Jakubec、Dušan Berkeš

  DOI：10.1016/j.tetasy.2010.11.015

  日期：2010.12

  A novel synthesis of highly enantioenriched dipeptides containing homophenylalanine is described. The process involves a crystallisation-induced asymmetric transformation (CIAT) in a Michael addition followed by exhaustive reduction. A unique example of a formally stereodivergent CIAT in conjugate addition of an achiral N-nucleophile to enantiomerically pure Michael acceptor has been discovered. (C) 2010 Elsevier Ltd. All rights reserved.