(3S,4S,5S)-3-chloro-4-hydroxy-5-methyl-1-heptene

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (3S,4S,5S)-3-chloro-4-hydroxy-5-methyl-1-heptene
• 英文别名: (3S,4S,5S)-3-chloro-5-methylhept-1-en-4-ol
• 化学式: C₈H₁₅ClO
• 分子量: 162.66
• InChiKey: FOCAQQVOHRICAI-FXQIFTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S)-3-chloro-4-hydroxy-5-methyl-1-heptene 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以98%的产率得到(3R,4S,5S)-3,4-epoxy-5-methyl-1-heptene
  参考文献：
  名称：

  Diastereoselective Chloroallylboration of α-Chiral Aldehydes

  摘要：

  Double asymmetric reaction of chiral (Z)-(gamma-chloroallyl)borane, 2, with alpha-chiral aldehydes (3-7) provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins (8-17) and vinyl epoxides(18-27). Both enantiomers of 2 exhibited excellent diatereoselectivity (greater than or equal to 90 de) for matched cases. The mismatched cases yielded moderate to good diastereoselectivity.

  DOI：

  10.1021/jo980977a
• 作为产物：
  描述：

  (S)-2-甲基丁醛 、 3-氯丙烯 在 ^lIpc₂BOMe 、 三氟化硼乙醚 、 lithium dicyclohexylamide 作用下， 生成 (3R,4R,5S)-3-chloro-4-hydroxy-5-methyl-1-heptene 、 (3S,4S,5S)-3-chloro-4-hydroxy-5-methyl-1-heptene
  参考文献：
  名称：

  Diastereoselective Chloroallylboration of α-Chiral Aldehydes

  摘要：

  Double asymmetric reaction of chiral (Z)-(gamma-chloroallyl)borane, 2, with alpha-chiral aldehydes (3-7) provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins (8-17) and vinyl epoxides(18-27). Both enantiomers of 2 exhibited excellent diatereoselectivity (greater than or equal to 90 de) for matched cases. The mismatched cases yielded moderate to good diastereoselectivity.

  DOI：

  10.1021/jo980977a

文献信息

• Diastereoselective Chloroallylboration of α-Chiral Aldehydes
  作者：Shaojing Hu、Seetharaman Jayaraman、Allan C. Oehlschlager

  DOI：10.1021/jo980977a

  日期：1998.11.1

  Double asymmetric reaction of chiral (Z)-(gamma-chloroallyl)borane, 2, with alpha-chiral aldehydes (3-7) provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins (8-17) and vinyl epoxides(18-27). Both enantiomers of 2 exhibited excellent diatereoselectivity (greater than or equal to 90 de) for matched cases. The mismatched cases yielded moderate to good diastereoselectivity.