(2S)-(-)-1-fluorooct-7-en-2-ol | 316140-39-3

• 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: (2S)-(-)-1-fluorooct-7-en-2-ol
• 英文别名: (2S)-1-fluorooct-7-en-2-ol
• CAS: 316140-39-3
• 化学式: C₈H₁₅FO
• 分子量: 146.205
• InChiKey: ULSSBWCRQDXPBT-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  6
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-(-)-1-fluorooct-7-en-2-ol 在 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium (0) 、 lithium chloride 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲苯 为溶剂， 反应 66.5h， 生成 (2'S)-(-)-1'-fluorooct-7'-en-2'-yl 2-allyl-4,6-dimethoxybenzoate
  参考文献：
  名称：

  Enantioselective Synthesis of a Fluorinated Analogue of the Orsellinic Acid-Type Twelve-Membered Lactone Lasiodiplodin

  摘要：

  The chemoenzymatic synthesis of the racemate and the one enantiomer of the fluorinated analogue 8 of the natural cyclooxygenase inhibitor lasiodiplodin is decribed. A lipase-mediated deracemization of the fluorohydrin 18 provided the chiral, nonracemic building block for the enantioselective synthesis of the title compound. The key step was the formation of the 12-membered lactone by a ring-closing metathesis.

  DOI：

  10.1021/jo0012445
• 作为产物：
  描述：

  (7S)-(+)-7-acetoxy-8-fluorooct-1-ene 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到(2S)-(-)-1-fluorooct-7-en-2-ol
  参考文献：
  名称：

  Enantioselective Synthesis of a Fluorinated Analogue of the Orsellinic Acid-Type Twelve-Membered Lactone Lasiodiplodin

  摘要：

  The chemoenzymatic synthesis of the racemate and the one enantiomer of the fluorinated analogue 8 of the natural cyclooxygenase inhibitor lasiodiplodin is decribed. A lipase-mediated deracemization of the fluorohydrin 18 provided the chiral, nonracemic building block for the enantioselective synthesis of the title compound. The key step was the formation of the 12-membered lactone by a ring-closing metathesis.

  DOI：

  10.1021/jo0012445

文献信息

• Enantioselective Synthesis of a Fluorinated Analogue of the Orsellinic Acid-Type Twelve-Membered Lactone Lasiodiplodin
  作者：Martina Runge、Günter Haufe

  DOI：10.1021/jo0012445

  日期：2000.12.1

  The chemoenzymatic synthesis of the racemate and the one enantiomer of the fluorinated analogue 8 of the natural cyclooxygenase inhibitor lasiodiplodin is decribed. A lipase-mediated deracemization of the fluorohydrin 18 provided the chiral, nonracemic building block for the enantioselective synthesis of the title compound. The key step was the formation of the 12-membered lactone by a ring-closing metathesis.