3-(2-(4-chlorophenyl)-4-diphenylbut-3-yn-2-yl)-1-methyl-1H-indole | 1033757-59-3

• 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-chlorophenyl)-4-diphenylbut-3-yn-2-yl)-1-methyl-1H-indole
• 英文别名: 3-(2-(4-chlorophenyl)-4-phenylbut-3-yn-2-yl)-1-methyl-1H-indole；3-[2-(4-Chlorophenyl)-4-phenylbut-3-yn-2-yl]-1-methylindole
• CAS: 1033757-59-3
• 化学式: C₂₅H₂₀ClN
• 分子量: 369.894
• InChiKey: QXARBXQSLWWTIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-(2-(4-chlorophenyl)-4-diphenylbut-3-yn-2-yl)-1-methyl-1H-indole 在 selenium 、 磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以94%的产率得到3-(4-(4-chlorophenyl)-5-phenylselenophen-3-yl)-1-methyl-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
• 作为产物：
  描述：

  2-(4-chlorophenyl)-4-phenylbut-3-yn-2-ol 、 1-甲基吲哚 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以72%的产率得到3-(2-(4-chlorophenyl)-4-diphenylbut-3-yn-2-yl)-1-methyl-1H-indole
  参考文献：
  名称：

  Brønsted Acid Catalyzed C3-Selective Propargylation and Benzylation of Indoles with Tertiary Alcohols

  摘要：

  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。

  DOI：

  10.1055/s-2008-1072584

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。
• SeCl₂-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
  作者：Guilherme M. Martins、Davi F. Back、Teodoro S. Kaufman、Claudio C. Silveira

  DOI：10.1021/acs.joc.8b00166

  日期：2018.3.16

  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.