(2'S)-(-)-1'-fluorooct-7'-en-2'-yl 2-hydroxy-4,6-dimethoxybenzoate | 316140-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2'S)-(-)-1'-fluorooct-7'-en-2'-yl 2-hydroxy-4,6-dimethoxybenzoate
• 英文别名: [(2S)-1-fluorooct-7-en-2-yl] 2-hydroxy-4,6-dimethoxybenzoate
• CAS: 316140-42-8
• 化学式: C₁₇H₂₃FO₅
• 分子量: 326.365
• InChiKey: ICCHMAPUHHTOGU-LBPRGKRZSA-N

物化性质

• 沸点：
  461.5±45.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2'S)-(-)-1'-fluorooct-7'-en-2'-yl 2-hydroxy-4,6-dimethoxybenzoate 在 吡啶 、 Grubbs catalyst first generation 、 tris(dibenzylideneacetone)dipalladium (0) 、 lithium chloride 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 100.0h， 生成 (7S)-(+)-7-fluoromethyl-2,4-dimethoxy-7,8,9,10,11,14-hexahydro-6-oxabenzocyclododecen-5-one
  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 4-二甲氨基吡啶 、 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 4.5h， 生成 (2'S)-(-)-1'-fluorooct-7'-en-2'-yl 2-hydroxy-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

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.