4,6,6-三甲基-1,3-环己二烯-1-甲酰氯 | 179104-42-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 4,6,6-三甲基-1,3-环己二烯-1-甲酰氯
• 英文名称: 4,6,6-Trimethylcyclohexa-1,3-dienecarbonyl chloride
• 英文别名: 1,3-Cyclohexadiene-1-carbonylchloride, 4,6,6-trimethyl-；4,6,6-trimethylcyclohexa-1,3-diene-1-carbonyl chloride
• CAS: 179104-42-8
• 化学式: C₁₀H₁₃ClO
• 分子量: 184.666
• InChiKey: HGKHQFHUXCJYMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  吲哚 、 4,6,6-三甲基-1,3-环己二烯-1-甲酰氯 在 乙基溴化镁 、 zinc(II) chloride 作用下， 以 乙醚 、 苯 为溶剂， 以80%的产率得到Indol-3'-yl 4,6,6-trimethylcyclohexa-1,3-dienyl ketone
  参考文献：
  名称：

  Synthesis of inverto-yuehchukene and its 10-(indol-3′-yl) isomer. X-Ray structure of (4aRS,10aRS)-1,1,3-trimethyl-1,2,4a,5,10,10a-hexahydroindene [1,2-b]indol-10-one

  摘要：

  A total synthesis of inverto-yuehchukene 4 and its 10-(indo-3'-yl) isomer 7 is described. The key tetracyclic ketone intermediate 13 was synthesized by a coupling reaction between 3-indolylzinc reagent and acid chloride 11, followed by Nazarov cyclization of the divinyl ketone 12. The indol-2-yl moiety present in inverto-yuehchukene 4 was introduced by palladium(0)-catalysed cross-coupling between indol-2-ylzinc reagent and the acetate 16.

  DOI：

  10.1039/p19960001213
• 作为产物：
  描述：

  4,6,6-三甲基环己-1,3-二烯羧酸 在 草酰氯 作用下， 以 苯 为溶剂， 反应 2.0h， 以80%的产率得到4,6,6-三甲基-1,3-环己二烯-1-甲酰氯
  参考文献：
  名称：

  Synthesis of inverto-yuehchukene and its 10-(indol-3′-yl) isomer. X-Ray structure of (4aRS,10aRS)-1,1,3-trimethyl-1,2,4a,5,10,10a-hexahydroindene [1,2-b]indol-10-one

  摘要：

  A total synthesis of inverto-yuehchukene 4 and its 10-(indo-3'-yl) isomer 7 is described. The key tetracyclic ketone intermediate 13 was synthesized by a coupling reaction between 3-indolylzinc reagent and acid chloride 11, followed by Nazarov cyclization of the divinyl ketone 12. The indol-2-yl moiety present in inverto-yuehchukene 4 was introduced by palladium(0)-catalysed cross-coupling between indol-2-ylzinc reagent and the acetate 16.

  DOI：

  10.1039/p19960001213

文献信息

• Synthesis of inverto-yuehchukene and its 10-(indol-3′-yl) isomer. X-Ray structure of (4aRS,10aRS)-1,1,3-trimethyl-1,2,4a,5,10,10a-hexahydroindene [1,2-b]indol-10-one
  作者：Kin-Fai Cheng、Man-Ki Cheung

  DOI：10.1039/p19960001213

  日期：——

  A total synthesis of inverto-yuehchukene 4 and its 10-(indo-3'-yl) isomer 7 is described. The key tetracyclic ketone intermediate 13 was synthesized by a coupling reaction between 3-indolylzinc reagent and acid chloride 11, followed by Nazarov cyclization of the divinyl ketone 12. The indol-2-yl moiety present in inverto-yuehchukene 4 was introduced by palladium(0)-catalysed cross-coupling between indol-2-ylzinc reagent and the acetate 16.