3-(2,4-diphenylbut-3-yn-2-yl)-1,2-dimethyl-1H-indole | 1084888-28-7

• 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)-1,2-dimethyl-1H-indole
• 英文别名: 1,2-dimethyl-3-(2,4-diphenylbut-3-yn-2-yl)-1H-indole；3-(2,4-Diphenylbut-3-yn-2-yl)-1,2-dimethylindole
• CAS: 1084888-28-7
• 化学式: C₂₆H₂₃N
• 分子量: 349.475
• InChiKey: VWMPIBKMDUMTLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 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-diphenylbut-3-yn-2-yl)-1,2-dimethyl-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89%的产率得到3-(2,4-diphenylselenophen-3-yl)-1,2-dimethyl-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：

  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 3.0h， 生成 3-(2,4-diphenylbut-3-yn-2-yl)-1,2-dimethyl-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 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。
• Synthesis of Diverse Indole-Containing Scaffolds by Gold(I)-Catalyzed Tandem Reactions of 3-Propargylindoles Initiated by 1,2-Indole Migrations: Scope and Computational Studies
  作者：Roberto Sanz、Delia Miguel、Mukut Gohain、Patricia García-García、Manuel A. Fernández-Rodríguez、Adán González-Pérez、Olalla Nieto-Faza、Ángel R. de Lera、Félix Rodríguez

  DOI：10.1002/chem.201001162

  日期：2010.8.23

  Similar to propargylic carboxylates and sulphides, 3‐propargylindoles undergo 1,2‐indole migrations under cationic gold(I) catalysis. The intermediate Au–carbenoid complex may evolve through different pathways depending on the substituents at the propargylic and terminal positions of the alkyne moiety. Thus, 3‐indenylindole derivatives were easily obtained through formal iso‐Nazarov or Nazarov cyclizations

  类似于炔丙基羧酸盐和硫化物，3-炔丙基吲哚在阳离子金（I）催化下经历1,2-吲哚迁移。取决于炔基部分的炔丙基和末端位置的取代基，中间的金-类胡萝卜素配合物可能通过不同的途径演化。因此，可以通过正式的iso-Nazarov或Nazarov环化轻松获得3-茚基吲哚衍生物。DFT计算支持形成亚烷基环丙烷中间体，该中间体在选择环开环后会经历金-异-纳扎罗夫或金-纳扎罗夫的环化反应。此外，3-dienylindoles可以访问时没有提到途径是可访问的，因此，中间的Au-卡宾络合物经由1,2--C进化H插入反应。我们还证明了最终产品可以通过一锅法从容易获得的炔丙醇和吲哚获得。
• 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。
• Gold(I)-Catalyzed Tandem Reactions Initiated by 1,2-Indole Migrations
  作者：Roberto Sanz、Delia Miguel、Félix Rodríguez

  DOI：10.1002/anie.200802660

  日期：2008.9.8