1'-fluorooct-7'-en-2'-yl 2,4-dimethoxy-6-trifluoromethanesulfonatebenzoate | 316140-41-7

• 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: 1'-fluorooct-7'-en-2'-yl 2,4-dimethoxy-6-trifluoromethanesulfonatebenzoate
• 英文别名: 1-Fluorooct-7-en-2-yl 2,4-dimethoxy-6-(trifluoromethylsulfonyloxy)benzoate
• CAS: 316140-41-7
• 化学式: C₁₈H₂₂F₄O₇S
• 分子量: 458.428
• InChiKey: ZYCXSDLWRCVNTE-UHFFFAOYSA-N

物化性质

• 沸点：
  530.5±50.0 °C(predicted)
• 密度：
  1.297±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1'-fluorooct-7'-en-2'-yl 2,4-dimethoxy-6-trifluoromethanesulfonatebenzoate 在 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 76.0h， 生成 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：

  1,7-辛二烯 在 吡啶 、 4-二甲氨基吡啶 、 18-冠醚-6 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 82.5h， 生成 1'-fluorooct-7'-en-2'-yl 2,4-dimethoxy-6-trifluoromethanesulfonatebenzoate
  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.