tert-butyl 2-[(4,6,6-trimethylcyclohexa-1,3-dienyl)carbonyl]indole-1-carboxylate | 266000-35-5

• 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-[(4,6,6-trimethylcyclohexa-1,3-dienyl)carbonyl]indole-1-carboxylate
• 英文别名: Tert-butyl 2-(4,6,6-trimethylcyclohexa-1,3-diene-1-carbonyl)indole-1-carboxylate
• CAS: 266000-35-5
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: IKGQVUGKNPHYRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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-[(4,6,6-trimethylcyclohexa-1,3-dienyl)carbonyl]indole-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以70%的产率得到6-Oxo-7,7,9-trimethyl-5,6,6aβ,7,8,10aβ-hexahydroindeno-<2,1-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：

  一氧化碳 、 lithium triethyl(1-tert-butoxycarbonylindol-2-yl)borate 、 4,6,6-trimethylcyclohexa-1,3-dienyl (trifluoromethyl)sulfonate 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 60.0 ℃ 、1.01 MPa 条件下， 反应 20.0h， 以75%的产率得到tert-butyl 2-[(4,6,6-trimethylcyclohexa-1,3-dienyl)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

• Total Synthesis of Yuehchukene
  作者：Minoru Ishikura、Katsuaki Imaizumi、Nobuya Katagiri

  DOI：10.3987/com-99-8822

  日期：——

  Total synthesis of yuehchukene could be realized through the palladium catalyzed carbonylative cross-coupling reaction of indolylborate (2 b) with cyclohexadienyl triflate (9) as a key reaction.
• 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.