3-(2,4-diphenylbut-3-yn-2-yl)-1H-indole | 1033757-64-0

• 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-(2,4-diphenylbut-3-yn-2-yl)-1H-indole
• CAS: 1033757-64-0
• 化学式: C₂₄H₁₉N
• 分子量: 321.422
• InChiKey: GGWQEDIGCCKQRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-(2,4-diphenylbut-3-yn-2-yl)-1H-indole 在 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以50%的产率得到3-(3-methyl-1-phenyl-1H-inden-2-yl)-1H-indole
  参考文献：
  名称：

  由1，2-吲哚迁移引发的金（I）催化串联反应。

  摘要：

  DOI：

  10.1002/anie.200802660
• 作为产物：
  描述：

  苯乙炔 在 cerium(III) chloride 、 potassium tert-butylate 、 zinc(II) oxide 作用下， 以 硝基甲烷 为溶剂， 反应 3.5h， 生成 3-(2,4-diphenylbut-3-yn-2-yl)-1H-indole
  参考文献：
  名称：

  SeCl₂-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes

  摘要：

  A novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,2-indolyl shift prompted by the electrophilic addition of SeCl2 to the triple bond of the propargyl indole, followed by cyclization through the intermediacy of a 1-seleno-1,3-diene. The reaction takes place at room temperature and shows excellent selectivity, broad substrate scope, and wide functional group tolerance.

  DOI：

  10.1021/acs.joc.8b00166

文献信息

• Brønsted Acid Catalyzed C3-Selective Propargylation and Benzylation of Indoles with Tertiary Alcohols
  作者：Roberto Sanz、Delia Miguel、Julia Álvarez-Gutiérrez、Félix Rodríguez

  DOI：10.1055/s-2008-1072584

  日期：——

  A Brønsted acid catalyzed C3-selective tert-alkylation of indoles using tertiary propargylic and benzylic alcohols has been developed. New C3-propargylated indole derivatives with a quaternary carbon at the propargylic position have been efficiently synthesized. Reactions were performed in air with undried solvents, and water was the only side product of the process.

  一种利用三级炔丙基和苄基醇对吲哚进行C3选择性叔烷基化的Brønsted酸催化方法已被开发出来。在炔丙基位置带有季碳的新型C3-炔丙基化吲哚衍生物已被高效合成。反应在空气中进行，使用未干燥的溶剂，过程的唯一副产品是水。
• Brønsted Acid Catalyzed Alkylation of Indoles with Tertiary Propargylic Alcohols: Scope and Limitations
  作者：Roberto Sanz、Delia Miguel、Alberto Martínez、Mukut Gohain、Patricia García-García、Manuel A. Fernández-Rodríguez、Estela Álvarez、Félix Rodríguez

  DOI：10.1002/ejoc.201001055

  日期：2010.12

  Junta de Castilla y Leon (BU021A09 and GR-172) and the Ministerio de Educacion y Ciencia (MEC) and FEDER (CTQ2007-61436/BQU and CTQ2009-09949/BQU) for financial support. D. M. and A. M. thank the MEC for MEC-FPU predoctoral fellowships. M. G. thanks the MEC for a "Young Foreign Researchers" contract (SB2006-0215). M. A. F.-R. and P. G.-G. also thank the MEC for "Ramon y Cajal" and "Juan de la Cierva"

  Junta de Castilla y Leon (BU021A09 和 GR-172) 以及教育部长 (MEC) 和 FEDER (CTQ2007-61436/BQU 和 CTQ2009-09949/BQU) 提供财政支持。DM 和 AM 感谢 MEC 提供 MEC-FPU 博士前奖学金。MG 感谢 MEC 的“外国青年研究人员”合同 (SB2006-0215)。MAF-R。和PG-G。还要感谢 MEC 的“Ramon y Cajal”和“Juan de la Cierva”合同。
• Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles
  作者：Estela Álvarez、Delia Miguel、Patricia García-García、Manuel A Fernández-Rodríguez、Félix Rodríguez、Roberto Sanz

  DOI：10.3762/bjoc.7.89

  日期：——

  The selectivity of our previously described gold-catalyzed tandem reaction, 1,2-indole migration followed by aura-iso-Nazarov cyclization, of 3-propargylindoles bearing (hetero)aromatic substituents at both the propargylic and terminal positions, was reversed by the proper choice of the catalyst and the reaction conditions. Thus, 3-(inden-2-yl)indoles, derived from an aura-Nazarov cyclization (instead of an aura-iso-Nazarov cyclization), were obtained in moderate to good yields from a variety of 3-propargylindoles.

  我们先前描述的金催化串联反应的选择性，即1,2-吲哚迁移，接着是aura-iso-Nazarov环化，对带有(杂)芳基取代基的3-丙炔基吲哚在丙炔基和末端位置的选择性进行了逆转，通过正确选择催化剂和反应条件。因此，从各种3-丙炔基吲哚中，得到了源自aura-Nazarov环化（而不是aura-iso-Nazarov环化）的3-(茚-2-基)吲哚，产率为中等到良好。
• An Al(OTf)3-catalyzed environmentally benign process for the propargylation of indoles
  作者：Mukut Gohain、Charlene Marais、Barend C.B. Bezuidenhoudt

  DOI：10.1016/j.tetlet.2012.06.095

  日期：2012.8

  Al(OTf)(3) catalyzed the alkylation of indoles using secondary/tertiary propargylic alcohols to produce 3-propargylated indoles in excellent yields with high selectivity. The reactions were performed in air with commercial grade solvents, and water was the only side product of the process. The catalyst was recovered after completion of the reaction and re-used with minimum loss of activity over three cycles. (c) 2012 Elsevier Ltd. All rights reserved.
• Anhydrous CeCl3 catalyzed C3-selective propargylation of indoles with tertiary alcohols
  作者：Claudio C. Silveira、Samuel R. Mendes、Lucas Wolf、Guilherme M. Martins

  DOI：10.1016/j.tetlet.2010.06.112

  日期：2010.8

  Anhydrous CeCl3 was successfully used as catalyst for the synthesis of several 3-propargyl indoles in good yields through the reaction of indole with propargyl alcohols in nitromethane. (C) 2010 Elsevier Ltd. All rights reserved.