(3R,5S)-methyl 3,5-dimethylheptanoate | 1011263-22-1

• 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: (3R,5S)-methyl 3,5-dimethylheptanoate
• 英文别名: methyl (3R,5S)-3,5-dimethylheptanoate
• CAS: 1011263-22-1
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: VIWHAEJWACQGQR-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (3R,5S)-methyl 3,5-dimethylheptanoate 、 甲氧羰基亚甲基三苯基正膦 在 二异丁基氢化铝 、 盐酸 作用下， 以 甲醇 、 正己烷 、 正庚烷 、 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 8.0h， 以59%的产率得到(5R,7S,E)-methyl 5,7-dimethylnon-2-enoate
  参考文献：
  名称：

  A Highly Catalytic Asymmetric Conjugate Addition:  Synthesis of the C14−C20 Fragment of Antibiotic TMC-151A, Siphonarienal and Siphonarienone

  摘要：

  A highly selective and general method for the synthesis of enantiopure deoxypropionates via the iterative application of CuI-ToI-BINAP-catalyzed asymmetric conjugate addition is described. This method gives access to all possible stereoisomers since both syn- and anti-deoxypropionates were obtained in high diastereoselectivities. The usefulness of the method is further exemplified by the preparation of two marine organisms, siphonarienal and siphonarienone, from commercially available trans-2-hexenoate.

  DOI：

  10.1021/ol702715q
• 作为产物：
  描述：

  (S,E)-methyl 5-methylhept-2-enoate 、 甲基溴化镁 在 copper(l) iodide 、 (R)-2,2'-bis[bis(3-methylphenyl)phosphino]-1,1'-binaphthyl 、 氯化铵 作用下， 以 乙醚 、 二氯甲烷 、 甲基叔丁基醚 、 甲醇 、 水 为溶剂， 以63%的产率得到(3R,5S)-methyl 3,5-dimethylheptanoate
  参考文献：
  名称：

  A Highly Catalytic Asymmetric Conjugate Addition:  Synthesis of the C14−C20 Fragment of Antibiotic TMC-151A, Siphonarienal and Siphonarienone

  摘要：

  A highly selective and general method for the synthesis of enantiopure deoxypropionates via the iterative application of CuI-ToI-BINAP-catalyzed asymmetric conjugate addition is described. This method gives access to all possible stereoisomers since both syn- and anti-deoxypropionates were obtained in high diastereoselectivities. The usefulness of the method is further exemplified by the preparation of two marine organisms, siphonarienal and siphonarienone, from commercially available trans-2-hexenoate.

  DOI：

  10.1021/ol702715q