2,2-bis(2-methyl-1H-indol-3-yl)-1-phenylethanone | 1383935-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-bis(2-methyl-1H-indol-3-yl)-1-phenylethanone
• 英文别名: 2,2-bis(2-methyl-1H-indol-3-yl)-1-phenylethan-1-one
• CAS: 1383935-50-9
• 化学式: C₂₆H₂₂N₂O
• 分子量: 378.473
• InChiKey: VAFBCLHDQONDQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.65
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 苯基丙醇水合物 在 3-(2-bromothiophen-3-yl)-4-(5-methyl-2-phenyloxazol-4-yl)furan-2(5H)-one 作用下， 以 二氯甲烷 为溶剂， 以85 %的产率得到2,2-bis(2-methyl-1H-indol-3-yl)-1-phenylethanone
  参考文献：
  名称：

  溴二芳基乙烯光产酸剂催化醛/酮对吲哚进行弗里德尔-克来福特烷基化反应

  摘要：

  闭环位置有一个溴原子的二芳基乙烯 (DAE) 可催化紫外线或阳光诱导的 C-C 键合反应。光照射后，溴二芳基乙烯发生 6π-电环化 (6π-EC)，随后释放出一种酸物质，该酸物质催化吲哚与醛和靛红的双傅克加成反应，形成相应的三芳基甲烷和 3,3'-二芳基吲哚啉-2个。该方案适用于多种醛和靛红，以及作为亲电子试剂的查耳酮。可以耐受酸或氧化剂敏感的官能团，例如二茂铁、4-甲氧基苯基、噻吩、吡咯。机理研究表明，需要光来引发反应。

  DOI：

  10.1055/a-2270-3973

文献信息

• Photoredox Generated Vinyl Radicals: Synthesis of Bisindoles and β-Carbolines
  作者：Neha Chalotra、Ajaz Ahmed、Masood Ahmad Rizvi、Zakir Hussain、Qazi Naveed Ahmed、Bhahwal Ali Shah

  DOI：10.1021/acs.joc.8b02193

  日期：2018.12.7

  A photoredox catalyzed approach enabling use of alkynes as surrogate of 2-oxoaldehydes/1,2-diones is reported. The method overcomes the difficulty associated with application of unsubstituted aliphatic α-oxoaldehydes, which has hitherto limited their general use. Indoles, tryptamine, and tryptophan methyl ester participated in the reaction to give a variety of α-oxo based analogues. Quantum yield investigations

  据报道，光氧化还原催化的方法能够使用炔烃作为2-氧醛/ 1,2-二酮的替代物。该方法克服了与未取代的脂族α-氧醛的施用相关的困难，该困难迄今限制了它们的一般用途。吲哚，色胺和色氨酸甲酯参与了反应，得到了多种基于α-氧代的类似物。量子产率研究支持自由基链机制。
• An organocatalytic asymmetric Friedel–Crafts reaction of 2-substituted indoles with aldehydes: enantioselective synthesis of α-hydroxyl ketones by low loading of chiral phosphoric acid
  作者：Xiong-fei Deng、Ying-wei Wang、Shi-qi Zhang、Ling Li、Guang-xun Li、Gang Zhao、Zhuo Tang

  DOI：10.1039/c9cc09637j

  日期：——

  Therefore, hydroxyl alkylation of an aldehyde with indole is confronted with great challenges. Here, we report an efficient strategy for asymmetric hydroxyl alkylation of 2-substituted indoles with aldehydes under 0.1 mol% chiral phosphoric acid. A series of α-hydroxyl ketones were obtained in high yields (up to 99%) and good enantioselectivities (up to 97%).

  通过与羰基化合物的Friedel-Crafts反应使吲哚的羟烷基化是有用的策略。但是，由于容易形成双吲哚副产物，因此反应仅限于酮。因此，醛与吲哚的羟烷基化面临巨大挑战。在这里，我们报告了一种有效的策略，用于在0.1 mol％手性磷酸下用醛类对2取代的吲哚进行不对称羟烷基化。以高收率（最高99％）和良好的对映选择性（最高97％）获得了一系列α-羟基酮。
• Reductive Alkylation of α-Keto Imines Catalyzed by PTSA/FeCl₃: Synthesis of Indoles and 2,3′-Biindoles
  作者：P. Seetham Naidu、Sinki Kolita、Meenakshi Sharma、Pulak J. Bhuyan

  DOI：10.1021/acs.joc.5b00533

  日期：2015.6.19

  was developed. In the reaction protocol, three components were used in one pot and products were obtained in high yield in an easy workup procedure. The reaction occurred via initial reductive alkylation of α-keto imines, followed by a cyclization process in the presence of PTSA/FeCl3 as catalyst.

  开发了一种简单高效的合成高度官能化的吲哚和双吲哚的方法。在该反应方案中，在一个锅中使用了三种组分，并通过简单的后处理程序以高收率获得了产物。该反应通过α-酮亚胺的初始还原烷基化，然后在PTSA / FeCl 3作为催化剂的存在下的环化过程而发生。
• I2-promoted direct one-pot synthesis of 2,2-bisindolyl-1-arylethanones from multiform substrates arylethenes, 2-hydroxy-aromatic ketones, and carbinols
  作者：Feng-Cheng Jia、Yan-Ping Zhu、Mei-Cai Liu、Mi Lian、Qing-He Gao、Qun Cai、An-Xin Wu

  DOI：10.1016/j.tet.2013.06.054

  日期：2013.8

  An I-2-promoted domino protocol was developed to construct 2,2-bisindolyl-1-arylethanones from multiform substrates arylethenes, 2-hydroxy-aromatic ketones, and carbinols via three distinct pathways. Through a logical coupled oxidation/Friedel-Crafts alkylation domino process, a variety of 2,2-bisindolyl-1-arylethanones were synthesized in one-pot. (C) 2013 Elsevier Ltd. All rights reserved.
• Metal-Free sp³ C–H Bond Dual-(Het)arylation: I₂-Promoted Domino Process to Construct 2,2-Bisindolyl-1-arylethanones
  作者：Yan-ping Zhu、Mei-cai Liu、Feng-cheng Jia、Jing-jing Yuan、Qing-he Gao、Mi Lian、An-xin Wu

  DOI：10.1021/ol301366p

  日期：2012.7.6

  A molecular I-2-promoted sp(3) C-H bond dual-(het)arylation protocol was developed for the synthesis of 2,2-bisindolyl-1-arylethanones. Through a logical design, three mechanism-different reactions (iodination, Kornblum oxidation, and Friedel Crafts reaction) were assembled in a single reactor. A variety of 2,2-bisindolyl-1-aryl ethanones were synthesized from simple and readily available aryl methyl ketones and indoles. In the reaction, metal, base, and ligand were all avoidable.