1-fluorooct-7-en-2-ol | 127296-12-2

• 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: 1-fluorooct-7-en-2-ol
• CAS: 127296-12-2
• 化学式: C₈H₁₅FO
• 分子量: 146.205
• InChiKey: ULSSBWCRQDXPBT-UHFFFAOYSA-N

物化性质

• 沸点：
  198.4±30.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Predicted)

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：

  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 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：

  1,7-辛二烯 在 18-冠醚-6 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 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

• The combination of hydrogen fluoride salt and aluminium fluoride: an efficient solid reagent for epoxide opening to give fluorohydrins
  作者：Junko Ichihara、Terukiyo Hanafusa

  DOI：10.1039/c39890001848

  日期：——

  The combination of hydrogen fluoride salt and porous aluminium fluoride (MHF2–AlF3)(M = alkali metal) is a stable and efficient solid reagent for promoting the ring-opening reaction of simple aliphatic oxiranes to give the fluorohydrins under sonication, as a substitute for anhydrous hydrogen fluoride.

  氟化氢盐和多孔氟化铝（MHF 2 –AlF 3）（M =碱金属）的组合是一种稳定有效的固体试剂，可促进简单的脂肪族环氧乙烷的开环反应，在超声处理下生成氟代醇。替代无水氟化氢。
• Enantioselective ring-opening of epoxides by HF-reagents
  作者：Günter Haufe、Stefan Bruns、Martina Runge

  DOI：10.1016/s0022-1139(01)00486-9

  日期：2001.11

  The asymmetric ring opening of meso- and racemic-epoxides with different HF-reagents mediated by enantiopure (salen)chromium chloride provides optically active fluorohydrins with maximum 90% e.e. This reaction as well as lipase-catalyzed deracemization of a fluorohydrin is applied to synthesize a building block for the preparation of both enantiomers of a fluorinated analogue of the prostaglandin biosynthesis

  由对映纯（salen）氯化铬介导的具有不同HF试剂的内消旋和外消旋环氧化物的不对称开环提供了最大90％ee的旋光性氟代醇。该反应以及脂肪酶催化的氟代脱氢反应可用于合成使用环化烯烃复分解反应作为关键步骤，制备前列腺素生物合成抑制剂lasiodiplodin的氟化类似物的两种对映体的基本组成部分。
• 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.