1-methyl-3-pentyl-2-phenyl-1H-indole | 1153648-32-8

• 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: 1-methyl-3-pentyl-2-phenyl-1H-indole
• 英文别名: 1-Methyl-3-pentyl-2-phenylindole；1-methyl-3-pentyl-2-phenylindole
• CAS: 1153648-32-8
• 化学式: C₂₀H₂₃N
• 分子量: 277.409
• InChiKey: ZKBSBZAJEJSZNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-benzyl-2-ethynyl-N-methylaniline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium tert-butylate 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 1-methyl-3-pentyl-2-phenyl-1H-indole
  参考文献：
  名称：

  A new synthesis of indoles via intramolecular cyclization of ο-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO

  摘要：

  2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of o-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOr-Bu in DMSO at room temperature. A reaction mechanism involving alpha-aminoalkyl radical intermediates is suggested. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.002

文献信息

• Preparation of 2,3-disubstituted indoles by sequential Larock heteroannulation and silicon-based cross-coupling reactions
  作者：Scott E. Denmark、John D. Baird

  DOI：10.1016/j.tet.2008.10.043

  日期：2009.4

  A simple and convergent synthesis of 2,3-disubstituted indoles has been developed using a sequential Larock indole synthesis and silicon-based, cross-coupling reaction. Substituted 2-iodoanilines reacted with an alkynyldimethylsilyl tert-butyl ether to afford indole-2-silanols under the Larock heteroannulation conditions after hydrolysis. The corresponding sodium 2-indolylsilanolate salts successfully

  使用顺序 Larock 吲哚合成和基于硅的交叉偶联反应开发了 2,3-二取代吲哚的简单和收敛合成。在水解后的 Larock 杂环化条件下，取代的 2-碘苯胺与炔基二甲基甲硅烷基叔丁基醚反应得到吲哚-2-硅烷醇。相应的 2-吲哚基硅烷醇钠盐成功地与芳基溴化物和氯化物交叉偶联，得到多取代的吲哚。炔基二甲基甲硅烷基叔丁基醚作为掩蔽硅烷醇等价物的开发使杂环化过程顺利进行，并确定了适合的催化剂/配体组合，从而提供了简便的交叉偶联反应。
• A new synthesis of indoles via intramolecular cyclization of ο-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO
  作者：Yan-yan Chen、Jia-hua Chen、Niu-niu Zhang、Lin-miao Ye、Xue-Jing Zhang、Ming Yan

  DOI：10.1016/j.tetlet.2014.12.002

  日期：2015.1

  2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of o-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOr-Bu in DMSO at room temperature. A reaction mechanism involving alpha-aminoalkyl radical intermediates is suggested. (C) 2012 Elsevier Ltd. All rights reserved.