(+)-(3S,4R)-4-acetoxy-3-methylnonan-1-ol | 375825-66-4

• 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: (+)-(3S,4R)-4-acetoxy-3-methylnonan-1-ol
• 英文别名: [(3S,4R)-1-hydroxy-3-methylnonan-4-yl] acetate
• CAS: 375825-66-4
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: QFJZELZKFQTFDO-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(3S,4R)-4-acetoxy-3-methylnonan-1-ol 在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (+)-(4S,5R)-5-acetoxy-4-methylnonanonitrile
  参考文献：
  名称：

  Baker's yeast-mediated approach to (−)-cis- and (+)-trans-Aerangis lactones

  摘要：

  The first enantioselective synthesis of natural (-)-cis-Aerangis lactone (-)-1a and its (+)-trans-diastereoisomer (+)-lb is described. The key steps in the synthesis are: (i) the enantiospecific and 100% diastereoselective baker's yeast reduction of 1,4-keto acid 2, to afford enantiopure trans- cognac lactone (+)-10; (ii) the regioselective PPL-mediated hydrolysis of the primary acetate moiety of diacetate (+)-(3S,4R)-3, obtained from (+)-10. Chain elongation by one carbon atom via cyanide substitution, and inversion of the configuration of C(5) in nitrile derivative (+)-21a are also required to complete the synthetic route to (-)-1a. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00314-7
• 作为产物：
  描述：

  (+)-trans-cognac lactone 在 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 porcine pancreatic lipase 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 (+)-(3S,4R)-4-acetoxy-3-methylnonan-1-ol
  参考文献：
  名称：

  Baker's yeast-mediated approach to (−)-cis- and (+)-trans-Aerangis lactones

  摘要：

  The first enantioselective synthesis of natural (-)-cis-Aerangis lactone (-)-1a and its (+)-trans-diastereoisomer (+)-lb is described. The key steps in the synthesis are: (i) the enantiospecific and 100% diastereoselective baker's yeast reduction of 1,4-keto acid 2, to afford enantiopure trans- cognac lactone (+)-10; (ii) the regioselective PPL-mediated hydrolysis of the primary acetate moiety of diacetate (+)-(3S,4R)-3, obtained from (+)-10. Chain elongation by one carbon atom via cyanide substitution, and inversion of the configuration of C(5) in nitrile derivative (+)-21a are also required to complete the synthetic route to (-)-1a. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00314-7

文献信息

• Baker's yeast-mediated approach to (−)-cis- and (+)-trans-Aerangis lactones
  作者：Elisabetta Brenna、Claudia Dei Negri、Claudio Fuganti、Stefano Serra

  DOI：10.1016/s0957-4166(01)00314-7

  日期：2001.7

  The first enantioselective synthesis of natural (-)-cis-Aerangis lactone (-)-1a and its (+)-trans-diastereoisomer (+)-lb is described. The key steps in the synthesis are: (i) the enantiospecific and 100% diastereoselective baker's yeast reduction of 1,4-keto acid 2, to afford enantiopure trans- cognac lactone (+)-10; (ii) the regioselective PPL-mediated hydrolysis of the primary acetate moiety of diacetate (+)-(3S,4R)-3, obtained from (+)-10. Chain elongation by one carbon atom via cyanide substitution, and inversion of the configuration of C(5) in nitrile derivative (+)-21a are also required to complete the synthetic route to (-)-1a. (C) 2001 Elsevier Science Ltd. All rights reserved.