3-[1-(4-fluorophenyl)-3-phenylprop-2-ynyl]-1H-indole

• 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-(4-fluorophenyl)-3-phenylprop-2-ynyl]-1H-indole
• 化学式: C₂₃H₁₆FN
• 分子量: 325.385
• InChiKey: UORGGFLHNPJWGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• 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：
  1

反应信息

• 作为产物：
  描述：

  吲哚 、 1-(4-氟苯基)-3-苯基丙-2-炔-1-醇 在 indium(III) bromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.58h， 以92%的产率得到3-[1-(4-fluorophenyl)-3-phenylprop-2-ynyl]-1H-indole
  参考文献：
  名称：

  溴化铟 (III) 催化 α-芳基取代炔丙醇对杂芳烃体系的快速炔丙基化反应

  摘要：

  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。

  DOI：

  10.1055/s-2007-990797

文献信息

• PMA-Silica Gel Catalyzed Propargylation of Aromatic Compounds with Arylpropargyl Alcohols under Solvent-Free Conditions
  作者：Pabbaraja Srihari、Joolakanti Reddy、Satadru Mandal、Kamani Satyanarayana、Jhillu Yadav

  DOI：10.1055/s-2008-1067083

  日期：——

  PMA-silica gel has been utilized to catalyze efficiently the propargylation of aromatic compounds with arylpropargyl alcohols in the absence of solvent under environmentally benign conditions.

  PMA-硅胶已被用于在环境无害的条件下在无溶剂的情况下有效地催化芳族炔丙醇与芳基炔丙醇的炔丙基化反应。
• 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。
• Iodine-catalyzed C- and O-nucleophilic substitution reactions of aryl-propargyl methanols
  作者：P. Srihari、Dinesh C. Bhunia、P. Sreedhar、S.S. Mandal、J. Shyam Sunder Reddy、J.S. Yadav

  DOI：10.1016/j.tetlet.2007.09.123

  日期：2007.11

  Aryl propargylic methanols undergo C- and O-nucleophilic substitution reactions in the presence of a catalytic amount of iodine in short reaction times with good yields. (c) 2007 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.
• Amberlite IR-120H as an efficient and versatile solid phase catalyst for nucleophilic substitution of propargylic alcohols
  作者：Satheesh Gujarathi、Howard P. Hendrickson、Guangrong Zheng

  DOI：10.1016/j.tetlet.2013.04.120

  日期：2013.7

  A highly efficient Amberlite IR-120H resin mediated nucleophilic substitution of the hydroxyl group of propargylic alcohols with a wide range of nucleophiles is reported. The reactions were achieved under very mild conditions in excellent yields. (c) 2013 Elsevier Ltd. All rights reserved.