dihydrocinnamic acid 1-(1-oxy-pyridin-4-yl)ethyl ester | 866418-08-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dihydrocinnamic acid 1-(1-oxy-pyridin-4-yl)ethyl ester
• 英文别名: 1-(1-oxidopyridin-1-ium-4-yl)ethyl 3-phenylpropanoate
• CAS: 866418-08-8
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: FUXDMJFAWAHZOK-UHFFFAOYSA-N

物化性质

• 沸点：
  455.8±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.24
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  dihydrocinnamic acid 1-(1-oxy-pyridin-4-yl)ethyl ester 在 BES buffer 、 subtilisin E 、 calcium chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (S)-dihydrocinnamic acid 1-(1-oxy-pyridin-4-yl)ethyl ester 、 (R)-dihydrocinnamic acid 1-(1-oxy-pyridin-4-yl)ethyl ester 、 (1S)-1-(1-氧代-4-吡啶基)乙醇 、 (R)-1-(1-oxy-pyridin-4-yl)ethanol
  参考文献：
  名称：

  How Substrate Solvation Contributes to the Enantioselectivity of Subtilisin toward Secondary Alcohols

  摘要：

  The current rule to predict the enantiopreference of subtilisin toward secondary alcohols is based on the size of the substituents at the stereocenter and implies that the active site contains two differently sized pockets for these substituents. Several experiments are inconsistent with the current rule. First, the X-ray structures of subtilisin show there is only one pocket (the S1' pocket) approximately the size of a phenyl group to bind secondary alcohols. Second, the rule often predicts the incorrect enantiomer for reactions in water. To resolve these contradictions, we refine the current rule to show that subtilisin binds only one substituent of a secondary alcohol and leaves the other in solvent. To test this refined empirical rule, we show that the enantioselectivity of a series of secondary alcohols in water varied linearly with the difference in hydrophobicity (log P/P0) of the substituents. This hydrophobicity difference accounts for the solvation of one substituent in water.

  DOI：

  10.1021/ja0528937
• 作为产物：
  描述：

  dihydrocinnamic acid 1-pyridin-4-yl-ethyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到dihydrocinnamic acid 1-(1-oxy-pyridin-4-yl)ethyl ester
  参考文献：
  名称：

  How Substrate Solvation Contributes to the Enantioselectivity of Subtilisin toward Secondary Alcohols

  摘要：

  The current rule to predict the enantiopreference of subtilisin toward secondary alcohols is based on the size of the substituents at the stereocenter and implies that the active site contains two differently sized pockets for these substituents. Several experiments are inconsistent with the current rule. First, the X-ray structures of subtilisin show there is only one pocket (the S1' pocket) approximately the size of a phenyl group to bind secondary alcohols. Second, the rule often predicts the incorrect enantiomer for reactions in water. To resolve these contradictions, we refine the current rule to show that subtilisin binds only one substituent of a secondary alcohol and leaves the other in solvent. To test this refined empirical rule, we show that the enantioselectivity of a series of secondary alcohols in water varied linearly with the difference in hydrophobicity (log P/P0) of the substituents. This hydrophobicity difference accounts for the solvation of one substituent in water.

  DOI：

  10.1021/ja0528937