(-)-(R)-3-Benzyl-2-oxetanone | 462118-48-5

• 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: (-)-(R)-3-Benzyl-2-oxetanone
• 英文别名: (3R)-3-benzyloxetan-2-one
• CAS: 462118-48-5
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: ISVWQTQCIQCLOZ-SECBINFHSA-N

物化性质

• 沸点：
  283.3±9.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(R)-3-Benzyl-2-oxetanone 在 Tris buffer 、 α-chymotrypsin 作用下， 以 二甲基亚砜 为溶剂， 生成 (R)-2-苄基-3-羟基丙酸
  参考文献：
  名称：

  Cleavage of β-lactone ring by serine protease. Mechanistic implications

  摘要：

  Both enantiomers of 3-benzyl-2-oxctanone (1) were found to be slowly hydrolyzed substrates of a-chymotrypsin having k(cat) values of 0.134 +/- 0.008 and 0.105 +/- 0.004min(-1) for (R)-1 and (S)-1, respectively, revealing that alpha-CT is virtually unable to differentiate the enantiomers in the hydrolysis of 1. The initial step to form the acyl-enzyme intermediate by the attack of Ser-195 hydroxyl on the beta-lactone ring at the 2-position in the hydrolysis reaction may not be enzymatically driven, but the relief of high ring strain energy of beta-lactone may constitute a major driving force. The deacylation step is also attenuated, which is possibly due to the hydrogen bond that would be formed between the imidazole nitrogen of His-57 and the hydroxyl group generated during the acylation in the case of (R)-1, but in the alpha-CT catalyzed hydrolysis of (S)-1 the imidazole nitrogen may form a hydrogen bond with the ester carbonyl oxygen. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00108-6
• 作为产物：
  描述：

  2-benzyl-3-hydroxypropyl acetate 在 甲醇 、 sodium hydroxide 、 jones' reagent 、 phosphate buffer 、 水 、 potassium carbonate 、 乙酰氯 、 α-chymotrypsin 作用下， 以 丙酮 为溶剂， 反应 44.0h， 生成 (-)-(R)-3-Benzyl-2-oxetanone
  参考文献：
  名称：

  Cleavage of β-lactone ring by serine protease. Mechanistic implications

  摘要：

  Both enantiomers of 3-benzyl-2-oxctanone (1) were found to be slowly hydrolyzed substrates of a-chymotrypsin having k(cat) values of 0.134 +/- 0.008 and 0.105 +/- 0.004min(-1) for (R)-1 and (S)-1, respectively, revealing that alpha-CT is virtually unable to differentiate the enantiomers in the hydrolysis of 1. The initial step to form the acyl-enzyme intermediate by the attack of Ser-195 hydroxyl on the beta-lactone ring at the 2-position in the hydrolysis reaction may not be enzymatically driven, but the relief of high ring strain energy of beta-lactone may constitute a major driving force. The deacylation step is also attenuated, which is possibly due to the hydrogen bond that would be formed between the imidazole nitrogen of His-57 and the hydroxyl group generated during the acylation in the case of (R)-1, but in the alpha-CT catalyzed hydrolysis of (S)-1 the imidazole nitrogen may form a hydrogen bond with the ester carbonyl oxygen. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00108-6