bicyclo<2.2.1>heptanyl 3-hydroxybutanoate | 134080-54-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: bicyclo<2.2.1>heptanyl 3-hydroxybutanoate
• 英文别名: [(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl] (3S)-3-hydroxybutanoate
• CAS: 134080-54-9
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: PAMAPFIWFHNWFS-AXTSPUMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-1-phenylethyl-(S)-3-hydroxybutanoate 在 dichloro(1,5-cyclooctadiene)ruthenium(II) 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 作用下， 以 异丙醇 为溶剂， 25.0~30.0 ℃ 、20.26 MPa 条件下， 反应 58.0h， 以98%的产率得到bicyclo<2.2.1>heptanyl 3-hydroxybutanoate
  参考文献：
  名称：

  Yeast-mediated resolution of .beta.-keto esters of prochiral alcohols

  摘要：

  Several racemic alcohols were converted to their beta-keto esters with diketene, and the resulting compounds were subjected to kinetic resolution by means of bakers' yeast. The unreacted keto esters were separated from the reduced hydroxy esters by chromatography, and the products were analyzed for levels of enantiomeric excess. Chiral shift reagents, Mosher esters, and optical rotation of the enantiomers of the alcohols were the criteria used to determine the optical integrity of the resolved alcohols after hydrolysis of the esters. Absolute stereochemistry was determined for the resolution products of all the substrates. Some rationale is advanced to account for the observed levels of enantiomeric excess and for the apparent diastereospecificity of the enzymatic resolution. The utility of this process as means of resolution of prochiral alcohols as well as an application of such resolution to the preparation of both enantiomers of a pyrrolizidine alkaloid synthon are indicated.

  DOI：

  10.1021/jo00011a031

文献信息

• Yeast-mediated resolution of .beta.-keto esters of prochiral alcohols
  作者：Tomas Hudlicky、Toshiya Tsunoda、Kumar G. Gadamasetti、Jerry A. Murry、Gary E. Keck

  DOI：10.1021/jo00011a031

  日期：1991.5

  Several racemic alcohols were converted to their beta-keto esters with diketene, and the resulting compounds were subjected to kinetic resolution by means of bakers' yeast. The unreacted keto esters were separated from the reduced hydroxy esters by chromatography, and the products were analyzed for levels of enantiomeric excess. Chiral shift reagents, Mosher esters, and optical rotation of the enantiomers of the alcohols were the criteria used to determine the optical integrity of the resolved alcohols after hydrolysis of the esters. Absolute stereochemistry was determined for the resolution products of all the substrates. Some rationale is advanced to account for the observed levels of enantiomeric excess and for the apparent diastereospecificity of the enzymatic resolution. The utility of this process as means of resolution of prochiral alcohols as well as an application of such resolution to the preparation of both enantiomers of a pyrrolizidine alkaloid synthon are indicated.