(3S,5S)-6-benzyl-8,8-dimethyl-9-(naphthalen-1-ylmethyl)-7,10-dioxo-2,6,9-triazaspiro[4,5]decane-3-carboxylic acid trifluoroacetic acid | 1374959-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3S,5S)-6-benzyl-8,8-dimethyl-9-(naphthalen-1-ylmethyl)-7,10-dioxo-2,6,9-triazaspiro[4,5]decane-3-carboxylic acid trifluoroacetic acid
• 英文别名: (3S,5S)-6-benzyl-8,8-dimethyl-9-(naphthalen-1-ylmethyl)-7,10-dioxo-2,6,9-triazaspiro[4.5]decane-3-carboxylic acid;2,2,2-trifluoroacetic acid
• CAS: 1374959-12-2
• 化学式: C₂HF₃O₂*C₂₈H₂₉N₃O₄
• 分子量: 585.58
• InChiKey: GBYNOAPAZRIOPR-DVASCVOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 氢溴酸 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.67h， 生成 (3S,5S)-6-benzyl-8,8-dimethyl-9-(naphthalen-1-ylmethyl)-7,10-dioxo-2,6,9-triazaspiro[4,5]decane-3-carboxylic acid trifluoroacetic acid
  参考文献：
  名称：

  Hydrophobic Substituent Effects on Proline Catalysis of Aldol Reactions in Water

  摘要：

  Derivatives of 4-hydroxyproline with a series of hydrophobic groups in well-defined orientations have been tested as catalysts for the aldol reactions. All of the modified proline catalysts carry out the intermolecular aldol reaction in water and provide high diastereoselectivity and enantioselectivity. Modified prolines with aromatic groups syn to the carboxylic acid are better catalysts than those with small hydrophobic groups (1a is 43.5 times faster than 1f). Quantum mechanical calculations provide transition structures, TS-1a(water) and TS-1f(water), that support the hypothesis that a stabilizing hydrophobic interaction occurs with 1a.

  DOI：

  10.1021/jo300569c

文献信息

• Hydrophobic Substituent Effects on Proline Catalysis of Aldol Reactions in Water
  作者：Qingquan Zhao、Yu-hong Lam、Mahboubeh Kheirabadi、Chongsong Xu、K. N. Houk、Christian E. Schafmeister

  DOI：10.1021/jo300569c

  日期：2012.5.18

  Derivatives of 4-hydroxyproline with a series of hydrophobic groups in well-defined orientations have been tested as catalysts for the aldol reactions. All of the modified proline catalysts carry out the intermolecular aldol reaction in water and provide high diastereoselectivity and enantioselectivity. Modified prolines with aromatic groups syn to the carboxylic acid are better catalysts than those with small hydrophobic groups (1a is 43.5 times faster than 1f). Quantum mechanical calculations provide transition structures, TS-1a(water) and TS-1f(water), that support the hypothesis that a stabilizing hydrophobic interaction occurs with 1a.