tert-butyl 2-[(6,6-dimethylcyclohex-1-enyl)carbonyl]indole-1-carboxylate | 309718-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl 2-[(6,6-dimethylcyclohex-1-enyl)carbonyl]indole-1-carboxylate
• 英文别名: Tert-butyl 2-(6,6-dimethylcyclohexene-1-carbonyl)indole-1-carboxylate；tert-butyl 2-(6,6-dimethylcyclohexene-1-carbonyl)indole-1-carboxylate
• CAS: 309718-50-1
• 化学式: C₂₂H₂₇NO₃
• 分子量: 353.461
• InChiKey: IGOYPBAHJZHTLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(6,6-dimethylcyclohex-1-enyl)carbonyl]indole-1-carboxylate 在 europium(III) trifluoroacetate 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 21.0h， 生成 (6S,6aR,10aR)-6-indol-3-yl-7,7-dimethyl-5,6,6a,7,8,9,10,10a-octahydrobenzo[1',2'-1,5]cyclopenta[3,2-b]indole
  参考文献：
  名称：

  A Concise Preparation of Yuehchukene and Its Analogues

  摘要：

  The palladium catalyzed carbonylative cross-coupling reaction of indolylborates (2) with vinyl triflates (3) afforded indol-2-yl ketones (4), which were subsequently converted to hexahydroindeno[2,1-b]indoles (5) with the aid of an acid. This protocol was well adapted for the total synthesis of yuehchukene.

  DOI：

  10.3987/com-00-9008
• 作为产物：
  描述：

  1-Boc-吲哚 在 bis-triphenylphosphine-palladium(II) chloride 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 60.0 ℃ 、1.01 MPa 条件下， 反应 20.0h， 生成 tert-butyl 2-[(6,6-dimethylcyclohex-1-enyl)carbonyl]indole-1-carboxylate
  参考文献：
  名称：

  A Concise Preparation of Yuehchukene and Its Analogues

  摘要：

  The palladium catalyzed carbonylative cross-coupling reaction of indolylborates (2) with vinyl triflates (3) afforded indol-2-yl ketones (4), which were subsequently converted to hexahydroindeno[2,1-b]indoles (5) with the aid of an acid. This protocol was well adapted for the total synthesis of yuehchukene.

  DOI：

  10.3987/com-00-9008

文献信息

• A Concise Preparation of Yuehchukene and Its Analogues
  作者：Minoru Ishikura、Katsuaki Imaizumi、Nobuya Katagiri

  DOI：10.3987/com-00-9008

  日期：——

  The palladium catalyzed carbonylative cross-coupling reaction of indolylborates (2) with vinyl triflates (3) afforded indol-2-yl ketones (4), which were subsequently converted to hexahydroindeno[2,1-b]indoles (5) with the aid of an acid. This protocol was well adapted for the total synthesis of yuehchukene.