4-(1-methyl-1H-indol-3-yl)-4-phenylpent-2-yn-1-ol | 1396763-54-4

• 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: 4-(1-methyl-1H-indol-3-yl)-4-phenylpent-2-yn-1-ol
• CAS: 1396763-54-4
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: YRDPCEGAWPIGSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.16
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(1-methyl-1H-indol-3-yl)-4-phenylpent-2-yn-1-ol 在 偶氮二甲酸二异丙酯 、 2-硝基苯磺酰肼 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 1-methyl-3-(2-phenylpenta-3,4-dien-2-yl)-1H-indole
  参考文献：
  名称：

  Regioselective Synthesis of Elusive 4,9-Dihydro-1H-Carbazoles by Gold-Catalyzed Cycloisomerization of 3-Allenylmethylindoles

  摘要：

  A general and efficient synthesis of 4,9-dihydro-1H-carbazoles from 3-allenylmethylindoles is reported. The process, catalyzed by a cationic gold(I) complex, involves a formal C2-H bond activation of the indole unit by reaction with the allene. The nature of the substituents at the allylic and terminal positions of the allene moiety has a crucial effect on the regioselectivity of the cyclization, which is also influenced by the catalyst and the solvent employed. Moreover, some evidence of the contribution of different reaction routes is provided, which led us to propose a plausible multipathway mechanism consistent with all of the results described.

  DOI：

  10.1021/jo401388b
• 作为产物：
  描述：

  1-甲基吲哚 、 4-phenyl-2-pentyne-1,4-diol 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 以44%的产率得到4-(1-methyl-1H-indol-3-yl)-4-phenylpent-2-yn-1-ol
  参考文献：
  名称：

  Synthesis of 2-Indol-3-ylbenzofulvenes through a Tandem Reaction Catalyzed by Cationic Gold(I) Complexes

  摘要：

  A new access to benzofulvenes bearing an indol-3-yl substituent at C-2 has been developed. Treatment of 3-propargylindoles possessing an additional hydroxy group at the other propargylic position with a cationic gold(I) complex triggers a tandem 1,2-indole migration/aura-iso-Nazarov cyclization/elimination sequence that takes place under mild conditions.

  DOI：

  10.1055/s-0031-1290950

文献信息

• Regioselective Synthesis of Elusive 4,9-Dihydro-1<i>H</i>-Carbazoles by Gold-Catalyzed Cycloisomerization of 3-Allenylmethylindoles
  作者：Estela Álvarez、Patricia García-García、Manuel A. Fernández-Rodríguez、Roberto Sanz

  DOI：10.1021/jo401388b

  日期：2013.10.4

  A general and efficient synthesis of 4,9-dihydro-1H-carbazoles from 3-allenylmethylindoles is reported. The process, catalyzed by a cationic gold(I) complex, involves a formal C2-H bond activation of the indole unit by reaction with the allene. The nature of the substituents at the allylic and terminal positions of the allene moiety has a crucial effect on the regioselectivity of the cyclization, which is also influenced by the catalyst and the solvent employed. Moreover, some evidence of the contribution of different reaction routes is provided, which led us to propose a plausible multipathway mechanism consistent with all of the results described.
• Synthesis of 2-Indol-3-ylbenzofulvenes through a Tandem Reaction Catalyzed by Cationic Gold(I) Complexes
  作者：Roberto Sanz、Estela Álvarez、Delia Miguel、Patricia García-García、Manuel Fernández-Rodríguez、Félix Rodríguez

  DOI：10.1055/s-0031-1290950

  日期：2012.6

  A new access to benzofulvenes bearing an indol-3-yl substituent at C-2 has been developed. Treatment of 3-propargylindoles possessing an additional hydroxy group at the other propargylic position with a cationic gold(I) complex triggers a tandem 1,2-indole migration/aura-iso-Nazarov cyclization/elimination sequence that takes place under mild conditions.