3-(1,3-diphenylprop-2-ynyl)-9H-carbazole | 1000703-60-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(1,3-diphenylprop-2-ynyl)-9H-carbazole
• CAS: 1000703-60-5
• 化学式: C₂₇H₁₉N
• 分子量: 357.455
• InChiKey: MQPWWGSRIQHXEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,3-diphenyl-1-propyne 、 咔唑 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 硝基甲烷 为溶剂， 反应 3.5h， 以80%的产率得到3-(1,3-diphenylprop-2-ynyl)-9H-carbazole
  参考文献：
  名称：

  DDQ-mediated oxidative cross-coupling between propargylic sp3 and indoles sp2 carbons

  摘要：

  DDQ-catalyzed oxidative cross-coupling reaction between indoles and propargyl compounds is reported for the first time. The reaction involves direct carbon-carbon bond formation between sp(2) carbons of indoles and sp(3) carbons of propargylates to yield the corresponding propargyl indoles in good yields with high selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.075

文献信息

• Indium(III) Bromide Catalyzed Rapid Propargylation of Heteroaromatic Systems by α-Aryl-Substituted Propargyl Alcohols
  作者：J. Yadav、B. Reddy、K. Rao、G. Kumar

  DOI：10.1055/s-2007-990797

  日期：2007.10

  pyrrole, and furan underwent smooth coupling with propargylic alcohols in the presence of 10 mol% of indium(III) bromide under mild conditions to furnish exclusively propargylated heterocycles in excellent yields and high regioselectivity. The use of indium(III) bromide makes this procedure simple, convenient, and practical. The hydroxy groups of the propargylic alcohols were simply replaced by the nucleophiles

  在温和条件下，在 10 mol% 溴化铟 (III) 存在下，多种杂芳族化合物（如吲哚、咔唑、吡咯和呋喃）与炔丙基醇平滑偶联，以优异的收率和高区域选择性提供完全炔丙基化的杂环。溴化铟 (III) 的使用使该过程简单、方便且实用。炔丙醇的羟基以 SN 2' 方式简单地被亲核试剂取代。
• Condensation of propargylic alcohols with indoles and carbazole in [bmim][PF6]/Bi(NO3)3·5H2O: a simple high yielding propargylation method with recycling and reuse of the ionic liquid
  作者：G.G.K.S. Narayana Kumar、Gopalakrishnan Aridoss、Kenneth K. Laali

  DOI：10.1016/j.tetlet.2012.04.026

  日期：2012.6

  Propargylation of a variety of substituted indoles as well as mono- and di-propargylation of carbazole are achieved in 80-94% isolated yields by employing catalytic amounts (10 mol%) of the readily available Bi(NO3)(3)center dot 5H(2)O in [bmim][PF6] ionic liquid (IL), with repeated recycling and reuse of the IL. (C) 2012 Elsevier Ltd. All rights reserved.
• DDQ-mediated oxidative cross-coupling between propargylic sp3 and indoles sp2 carbons
  作者：G.L.V. Damu、J. Jon Paul Selvam、C. Venkata Rao、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2009.08.075

  日期：2009.11

  DDQ-catalyzed oxidative cross-coupling reaction between indoles and propargyl compounds is reported for the first time. The reaction involves direct carbon-carbon bond formation between sp(2) carbons of indoles and sp(3) carbons of propargylates to yield the corresponding propargyl indoles in good yields with high selectivity. (C) 2009 Elsevier Ltd. All rights reserved.