α,α-Bis-(1,2-dimethylindol-3-yl)toluol | 17371-60-7

• 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: α,α-Bis-(1,2-dimethylindol-3-yl)toluol
• 英文别名: 1,2,1',2'-tetramethyl-1H,1'H-2,2'-phenylmethanediyl-bis-indole；3,3'-(Phenylmethylene)bis(1,2-dimethyl-1H-indole)；3-[(1,2-dimethylindol-3-yl)-phenylmethyl]-1,2-dimethylindole
• CAS: 17371-60-7
• 化学式: C₂₇H₂₆N₂
• 分子量: 378.517
• InChiKey: CMDBLYFPVSCEGC-UHFFFAOYSA-N

物化性质

• 沸点：
  568.7±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  吲哚 、 α,α-Bis-(1,2-dimethylindol-3-yl)toluol 在 iron(III) chloride hexahydrate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以56%的产率得到3-((1H-indol-3-yl)(phenyl)methyl)-1,2-dimethyl-1H-indole
  参考文献：
  名称：

  FeCl 3 ·6H 2 O作为温和的对称双（吲哚基）甲烷亲核取代催化剂

  摘要：

  在本文中，不对称双（吲哚基）甲烷（BIM）和3-烷基吲哚衍生物是由具有各种亲核试剂（包括杂芳族/芳族化合物，烯丙基硅烷和炔基硅烷）的对称BIM平稳合成的。FeCl 3 ·6H 2 O被发现是这种亲核取代反应的温和高效催化剂，其中N-甲基-2-苯基吲哚在C sp 3 -C sp 2键断裂反应中表现为良好的离去基团。操作简便，廉价且对环境友好的催化剂，温和的反应条件，宽泛的官能团耐受性和该反应策略的可扩展性是本方法的优点。

  DOI：

  10.1021/acs.joc.0c02466
• 作为产物：
  描述：

  1,2-二甲基吲哚 、 苯甲醛 在 四丁基高氯酸铵 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以85%的产率得到α,α-Bis-(1,2-dimethylindol-3-yl)toluol
  参考文献：
  名称：

  阳极触发的醛阳离子自动催化杂芳烃的烷基化。

  摘要：

  通过使用醛将杂芳烃烷基化是增加分子复杂性的直接方法，但是通常涉及使用化学计量的氧化剂，强酸和高温。这项研究涉及通过在温和条件下使用醛而无需介体的高能效的杂芳烃电化学烷基化。有趣的是，石墨阳极可以引发醛阳离子物质，该醛阳离子物质是有效的自催化剂，可与多种杂芳烃反应，从而以极高的区域选择性和高收率生产相应的产物。与传统的电合成方法相比，此电触发反应为生产高价值化学品提供了一种节电且环保的途径。

  DOI：

  10.1002/cssc.201903397

文献信息

• Palladium-catalyzed carbonylative bis(indolyl)methanes synthesis with TFBen as the CO source
  作者：Xinxin Qi、Han-Jun Ai、Ning Zhang、Jin-Bao Peng、Jun Ying、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2018.03.028

  日期：2018.6

  An efficient and convenient palladium-catalyzed carbonylative procedure for the synthesis of bis(indolyl)methanes has been established for the first time. With TFBen (benzene-1,3,5-triyl triformate) as the solid CO source, aryl iodides and indoles were transformed into the corresponding bis(indolyl)methane derivatives in moderate to excellent yields.

  首次建立了一种高效，便捷的钯催化羰基化合成双（吲哚基）甲烷的方法。以TFBen（1,3,5-三甲酸三苯酯）为固体CO源，将芳基碘化物和吲哚以中等至极好的收率转化为相应的双（吲哚基）甲烷衍生物。
• Synthesis of carbazoles by a balanced four component condensation
  作者：Fabien Cochard、Marie Laronze、Philippe Sigaut、Janos Sapi、Jean-Yves Laronze

  DOI：10.1016/j.tetlet.2003.12.099

  日期：2004.2

  An access to functionalised tetrahydrocarbazoles by a multicomponent reaction including 2-substituted indoles, aromatic aldehydes and Meldrum's acid is described. (C) 2003 Elsevier Ltd. All rights reserved.
• Reactivity of the Chiral Metallic Brønsted Acid [(η⁶-<i>p</i>-MeC₆H₄<i>i</i>Pr)Ru(κ³<i>P</i>,<i>O,O</i>′-<b>POH</b>)][SbF₆]₂ (<b>POH</b> = (<i>S</i>_C1,<i>R</i>_C2)-Ph₂PC(Ph)HC(OH)HCH₂OMe) toward Aldimines
  作者：Pilar Pardo、Daniel Carmona、Pilar Lamata、Ricardo Rodrı́guez、Fernando J. Lahoz、Pilar Garcı́a-Orduña、Luis A. Oro

  DOI：10.1021/om501018r

  日期：2014.12.8

  Dichloromethane solutions of complex 1 catalyze both the aza-DielsAlder (ADA) reaction of aldimines with cyclopentadiene and the aza-FriedelCrafts (AFC) reaction between aldimines and indoles. Racemic adducts were obtained in both cases. NMR measurements of mixtures of the aldimine N-(4-methylbenzylidene)aniline (I) and 1, in a 20/1 molar ratio, reveal the formation of the deprotonated compound 2 and the corresponding iminium cation HI+ (HN+). This cation is responsible for the achiral catalysis. Below 273 K, in 1/1 molar ratio mixtures of 1 and I, the chiral species 1 center dot I (OH center dot center dot center dot N) and 2 center dot HI+ (O center dot center dot center dot HN+) were formed by intermolecular hydrogen bonding and proton transfer, respectively. The latter solutions catalyze stoichiometrically the ADA reaction between aldimine I and HCp with 16% ee. With 5 mol % of catalyst loading, a 6% ee can be obtained if the aldimine is slowly added to the solution (20 equiv in 60 h). Above 273 K, solutions containing 1 and aldimine I irreversibly evolve to the aniline complex 3, which was isolated as a racemic mixture. The molecular structure of 3 has been determined by X-ray diffractometric methods. Hydride 5, an intermediate in this reaction, has been isolated and spectroscopically characterized. On the basis of synthetic and spectroscopic studies, a plausible pathway for the formation of 3 from 1 is proposed.
• Anodically Triggered Aldehyde Cation Autocatalysis for Alkylation of Heteroarenes
  作者：Caiyan Liu、Zihui Xiao、Shuhua Wu、Yongli Shen、Kedong Yuan、Yi Ding

  DOI：10.1002/cssc.201903397

  日期：2020.4.21

  Alkylation of heteroarenes by using aldehydes is a direct approach to increase molecular complexity, which however often involves the use of stochiometric oxidant, strong acid, and high temperature. This study concerns an energy-efficient electrochemical alkylation of heteroarenes by using aldehydes under mild conditions without mediators. Interestingly, the graphite anode can trigger aldehyde cationic

  通过使用醛将杂芳烃烷基化是增加分子复杂性的直接方法，但是通常涉及使用化学计量的氧化剂，强酸和高温。这项研究涉及通过在温和条件下使用醛而无需介体的高能效的杂芳烃电化学烷基化。有趣的是，石墨阳极可以引发醛阳离子物质，该醛阳离子物质是有效的自催化剂，可与多种杂芳烃反应，从而以极高的区域选择性和高收率生产相应的产物。与传统的电合成方法相比，此电触发反应为生产高价值化学品提供了一种节电且环保的途径。
• FeCl₃·6H₂O as a Mild Catalyst for Nucleophilic Substitution of Symmetrical Bis(indoyl)methanes
  作者：Chayamon Chantana、Jaray Jaratjaroonphong

  DOI：10.1021/acs.joc.0c02466

  日期：2021.2.5

  In this paper, unsymmetrical bis(indolyl)methane (BIM) and 3-alkylindole derivatives are smoothly synthesized from symmetrical BIMs with a variety of nucleophiles including heteroaromatic/aromatic compounds, allylsilane and alkynylsilane. FeCl3·6H2O is found to be a mild and highly effective catalyst for this nucleophilic substitution reaction in which N-methyl-2-phenylindole behaves as a good leaving

  在本文中，不对称双（吲哚基）甲烷（BIM）和3-烷基吲哚衍生物是由具有各种亲核试剂（包括杂芳族/芳族化合物，烯丙基硅烷和炔基硅烷）的对称BIM平稳合成的。FeCl 3 ·6H 2 O被发现是这种亲核取代反应的温和高效催化剂，其中N-甲基-2-苯基吲哚在C sp 3 -C sp 2键断裂反应中表现为良好的离去基团。操作简便，廉价且对环境友好的催化剂，温和的反应条件，宽泛的官能团耐受性和该反应策略的可扩展性是本方法的优点。