2,2'-Dimethyl-3,3'-<α-methyl-benzyliden>-bis-indol | 96671-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,2'-Dimethyl-3,3'-<α-methyl-benzyliden>-bis-indol
• 英文别名: 2,2'-dimethyl-1H,1'H-3,3'-(1-phenyl-ethane-1,1-diyl)-bis-indole；1,1-bis-(2-methyl-indol-3-yl)-1-phenyl-ethane；1,1-Bis-(2-methyl-indol-3-yl)-1-phenyl-aethan；2-methyl-3-[1-(2-methyl-1H-indol-3-yl)-1-phenylethyl]-1H-indole
• CAS: 96671-61-3
• 化学式: C₂₆H₂₄N₂
• 分子量: 364.49
• InChiKey: CXBVYMDWFQVQEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 苯乙炔 在 gallium trihalide 作用下， 以 甲苯 为溶剂， 反应 7.5h， 以80%的产率得到2,2'-Dimethyl-3,3'-<α-methyl-benzyliden>-bis-indol
  参考文献：
  名称：

  Gallium(III) halide-catalyzed coupling of indoles with phenylacetylene: synthesis of bis(indolyl)phenylethanes

  摘要：

  Indoles undergo smooth coupling with phenylacetylene in the presence of 10mol% of gallium(III) chloride or gallium(III) bromide under mild conditions to afford the corresponding 1,1-bis(1H-3-indolyl)-1-phenylethanes in high yields and with high selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.126

文献信息

• The Gold-Catalyzed Hydroarylation of Alkynes with Electron-Rich Heteroarenes - A Kinetic Investigation and New Synthetic Possibilities
  作者：Jasmin Schießl、Matthias Rudolph、A. Stephen K. Hashmi

  DOI：10.1002/adsc.201600940

  日期：2017.2.20

  The gold‐catalyzed mono‐hydroarylation and two‐fold hydroarylation of alkynes with electron‐rich heteroarenes was analyzed by a 1H NMR kinetic study. The obtained rate constants for the decreasing alkyne concentration provide information on the reactivity of this addition reaction. The examinations show the orthogonal reactivity of gold and a proton for the two reaction steps. The first hydroarylation

  金催化单hydroarylation和炔烃的两倍hydroarylation与富电子杂芳烃用分析11 H NMR动力学研究。对于降低的炔烃浓度获得的速率常数提供了关于该加成反应的反应性的信息。检验显示出两个反应步骤中金和质子的正交反应性。第一次氢芳基化仅由金（I）促进，而第二步以质子为前提，该质子可逆地衍生自末端炔烃形成的σ，π-乙炔化物络合物或与溶剂相互作用。根据动力学数据，有可能以中等到良好的产率合成各种单加合物，此外，还探索了带有两个不同取代基的杂二加合物的合成。
• Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes
  作者：Euan B. McLean、Francesca M. Cutolo、Orla J. Cassidy、David J. Burns、Ai-Lan Lee

  DOI：10.1021/acs.orglett.0c02526

  日期：2020.9.4

  Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-catalyzed reaction can be fully switched to allow for isolation of the vinylindole products instead. Furthermore, this selective reaction can be utilized to synthesize the more difficult to access unsymmetrical BIMs from readily available starting materials.
• Oddo; Perotti, Gazzetta Chimica Italiana, 1930, vol. 60, p. 13,20
  作者：Oddo、Perotti

  DOI：——

  日期：——
• Reinecke et al., Tetrahedron Letters, 1963, p. 1183,1185
  作者：Reinecke et al.

  DOI：——

  日期：——