trans-3-Hydroxy-2-(3-indolyl)benzocyclopentane | 125879-71-2

• 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: trans-3-Hydroxy-2-(3-indolyl)benzocyclopentane
• CAS: 125879-71-2
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: LNJNIUILBLBPRX-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.02
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  吲哚 、 氧化茚 以 乙腈 为溶剂， 42.0 ℃ 、999.99 MPa 条件下， 反应 24.0h， 以58%的产率得到trans-3-Hydroxy-2-(3-indolyl)benzocyclopentane
  参考文献：
  名称：

  High-pressure organic chemistry. 10. Novel neutral alkylations of indoles and pyrroles with vinyl epoxides at high pressure

  摘要：

  DOI：

  10.1021/jo00296a079

文献信息

• High-Pressure Organic Chemistry. 19. High-Pressure-Promoted, Silica Gel-Catalyzed Reaction of Epoxides with Nitrogen Heterocycles¹^,
  作者：Hiyoshizo Kotsuki、Katsunori Hayashida、Tomoyasu Shimanouchi、Hitoshi Nishizawa

  DOI：10.1021/jo951106t

  日期：1996.1.1

  The reaction of epoxides with nitrogen heterocycles such as indoles, pyrroles, imidazoles, and pyrazoles was studied under both high-pressure and silica gel-catalyzed conditions. Whereas it has been reported that the treatment of indole with styrene aside at in kbar and 42 degrees C for 24 h gave 2-(3-indolyl)-2-phenylethanol in 56% yield, the same compound was obtained in 88% yield when the reaction was conducted on silica gel at rt for 1 week. Similarly, efficient reaction of epoxides with pyrroles, imidazoles, and pyrazoles was achieved. In terms of stereochemical features, the epoxide ring opening reaction of (R)-(+)-styrene oxide with indole was found to proceed stereoselectively in an S(N)2 fashion at the benzyl carbon, in either ease.