benzyl (R)-2-allyl-3-phenylpropanoate | 133871-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (R)-2-allyl-3-phenylpropanoate
• CAS: 133871-25-7
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: CZCMHNRKNAGKDM-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  benzyl (R)-2-allyl-3-phenylpropanoate 在 palladium on activated charcoal 氢气 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 2.42h， 生成 potassium (S)-2-benzyl-3-formylpropanoate
  参考文献：
  名称：

  Stereochemistry in enzyme inhibition: synthesis and evaluation of enantiomerically pure 2-benzyl-3-formylpropanoic acids as inhibitors of carboxypeptidase A

  摘要：

  Both enantiomers of 2-benzyl-3-formylpropanoic acid were synthesized in five steps starting with hydrocinnamic acid and each enantiomer assayed for inhibitory activity against carboxypeptidase A to find that the (R)-form is 674-fold more potent than its enantiomer. The finding that the (R)-form which belongs to the L-series is mostly responsible for the inhibitory activity accords with the explanation that the present inhibitor is a transition state analog inhibitor because, as such, its stereochemistry should belong to the same series as that of the substrate, i.e., the L-series. The gem-diol form of the inhibitor generated in situ mimics the transition state in the catalytic process.

  DOI：

  10.1016/s0957-4166(99)00421-8
• 作为产物：
  描述：

  2-benzyl-pent-4-enoyl chloride 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 benzyl (R)-2-allyl-3-phenylpropanoate
  参考文献：
  名称：

  Stereochemistry in enzyme inhibition: synthesis and evaluation of enantiomerically pure 2-benzyl-3-formylpropanoic acids as inhibitors of carboxypeptidase A

  摘要：

  Both enantiomers of 2-benzyl-3-formylpropanoic acid were synthesized in five steps starting with hydrocinnamic acid and each enantiomer assayed for inhibitory activity against carboxypeptidase A to find that the (R)-form is 674-fold more potent than its enantiomer. The finding that the (R)-form which belongs to the L-series is mostly responsible for the inhibitory activity accords with the explanation that the present inhibitor is a transition state analog inhibitor because, as such, its stereochemistry should belong to the same series as that of the substrate, i.e., the L-series. The gem-diol form of the inhibitor generated in situ mimics the transition state in the catalytic process.

  DOI：

  10.1016/s0957-4166(99)00421-8