bis(1-benzyl-1H-indol-3-yl)methane | 256391-50-1

• 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: bis(1-benzyl-1H-indol-3-yl)methane
• 英文别名: 1-Benzyl-3-[(1-benzylindol-3-yl)methyl]indole
• CAS: 256391-50-1
• 化学式: C₃₁H₂₆N₂
• 分子量: 426.561
• InChiKey: UIKFVPPUWSIMOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  bis(1-benzyl-1H-indol-3-yl)methane 、 三氟乙酸酐 以 苯 为溶剂， 反应 4.0h， 以33%的产率得到5,11-dihydro-5,11-dibenzyl-6-trifluoromethylindolo[3,2-b]carbazole
  参考文献：
  名称：

  Synthesis of a Trifluoromethylindolocarbazole, Novel Cyclic 27- and 36-Membered N-Benzyltri- and -tetraindoles, and an N-Benzyltetraindolyltrimethane

  摘要：

  5,11-Dihydro-5,11-dibenzyl-6-trifluoromethylindolo[3,2-b]carbazole (6) and the cyclic N-benzylindole trimer 4 were synthesized from both N-benzylindole-3-methanol (1) and N,N'-dibenzyl-3,3'-diindolylmethane (2) by treatment with trifluoroacetic anhydride. The former also gave the 36-membered cyclic N-benzylindole tetramer 7, and the latter furnished N-benzyl-3-trifluoroacetylindole (8). Heating 1 in aqueous methanol also yielded the trimer 4 along with 2, the N-benzylitriindolyldimethane 3, and the N-benzyltetraindolyltrimethane 5 whose structure and solid-state conformation were determined by X-ray crystallographic analysis. The results are discussed and plausible mechanisms of the reactions leading to 3-8 are presented.

  DOI：

  10.1007/pl00010184
• 作为产物：
  描述：

  溴甲苯 在 potassium hydroxide 、 copper dichloride 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 4.0h， 生成 bis(1-benzyl-1H-indol-3-yl)methane
  参考文献：
  名称：

  铜（II）催化的CH（SP3）氧化和CN裂解：使用四甲基乙二胺作为碳源的碱基转换的甲基化和甲酰化。

  摘要：

  使用四甲基乙二胺（TMEDA）作为碳源的碱转换的甲基化和甲酰化反应已在温和的条件下实现，由CuCl（2）催化，大气中的氧气作为氧化剂。合成了双吲哚甲烷，二苯基甲烷和3-甲酰基吲哚，具有良好的区域选择性和良好的收率。

  DOI：

  10.1039/c2cc32009f

文献信息

• Synthesis of Unnatural Arundines Using a Magnetically Reusable Copper Ferrite Catalyst
  作者：Nam Phan、Pha Ha、Oanh Nguyen、Khoa Huynh、Tung Nguyen

  DOI：10.1055/s-0037-1610227

  日期：2018.9

  We report a method for copper ferrite-catalyzed coupling of indoles and N , N -dimethylacetamide (DMA) to afford Arundine derivatives. Halogen, methoxy, boronate ester, and trimethylsilyl functionalities are compatible with reaction conditions. Unprotected or sterically hindered indoles are also competent substrates. Indoles containing competitively reactive pyrazoles deliver the desired products in

  我们报告了一种铜铁氧体催化的吲哚和 N，N-二甲基乙酰胺 (DMA) 偶联以提供 Arundine 衍生物的方法。卤素、甲氧基、硼酸酯和三甲基甲硅烷基官能团与反应条件相容。未受保护或空间位阻的吲哚也是有效的底物。含有竞争性反应性吡唑的吲哚以合理的产率提供所需的产品。铜铁氧体很容易回收和重复使用，最多可重复使用 9 次，而不会造成显着的产量损失。
• Copper-Catalyzed Coupling of Indoles with Dimethylformamide as a Methylenating Reagent
  作者：Fan Pu、Yang Li、Yong-Hong Song、Jianliang Xiao、Zhong-Wen Liu、Chao Wang、Zhao-Tie Liu、Jian-Gang Chen、Jian Lu

  DOI：10.1002/adsc.201500874

  日期：2016.2.18

  By using N,N‐dimethylformamide (DMF) as a methylenating reagent, the copper‐catalyzed CH activation of indole was demonstrated as an efficient and facile protocol for synthesizing 3,3′‐diindolylmethane (DIM) and its derivatives. The results indicate that copper chloride was the best catalyst among the investigated transition metal salts, which affords an excellent regioselectivity and good yield when

  通过使用N，N-二甲基甲酰胺（DMF），其为亚甲基化试剂时，铜催化Ç  ħ吲哚的活化被证明作为一种有效和容易的协议用于合成3,3-二吲哚基甲烷（DIM）和它的衍生物。结果表明，在所研究的过渡金属盐中，氯化铜是最好的催化剂，当使用叔丁基过氧化氢（TBHP）作为氧化剂时，氯化铜具有出色的区域选择性和良好的收率。
• Directly Bridging Indoles to 3,3′-Bisindolylmethanes by Using Carboxylic Acids and Hydrosilanes under Mild Conditions
  作者：Chang Qiao、Xiao-Fang Liu、Hong-Chen Fu、Hao-Peng Yang、Zhi-Bo Zhang、Liang-Nian He

  DOI：10.1002/asia.201800766

  日期：2018.9.17

  (BIMs) synthesis by reductive alkylation of indoles at the C3 position with carboxylic acids in the presence of hydrosilane was developed for the first time. Instead of aldehydes, more readily available, stable, and easy‐to‐handle carboxylic acids have been employed as alternative alkylating agents. As an efficient organocatalyst, B(C6F5)3 enables the reductive alkylation of various substituted indole

  首次开发了一种简单的路易斯酸促进的3,3'-二吲哚基甲烷（BIM）合成方法，该方法是在存在氢硅烷的情况下，通过羧酸在C3位的吲哚还原烷基化来合成3,3'-二吲哚基甲烷（BIM）。代替醛，更容易获得，稳定和易于处理的羧酸已被用作替代烷基化剂。作为有效的有机催化剂，B（C 6 F 5）3使在室温下和在纯净条件下，各种取代的吲哚衍生物与羧酸进行还原性烷基化反应，收率可达98％。这种无金属的策略为将吲哚直接用羧酸直接官能化为BIM提供了另一种方法，该方案允许将羧酸选择性还原为醛，并形成C-C键。
• Introducing tetramethylurea as a new methylene precursor: a microwave-assisted RuCl₃-catalyzed cross dehydrogenative coupling approach to bis(indolyl)methanes
  作者：Mohit L. Deb、Paran J. Borpatra、Prakash J. Saikia、Pranjal K. Baruah

  DOI：10.1039/c6ob02671k

  日期：——

  Herein we report a microwave assisted Ru(III)/TBHP-mediated reaction of indoles with tetramethylurea (TMU) synthesizing symmetrical as well as unsymmetrical bis(indolyl)methanes, where TMU acts as a methylenating agent. This is the first report where TMU is used as a methylene source. Moreover, the synthesis of unsymmetrical bis(indolyl)methanes by using a carbon precursor is also reported herein for

  本文中，我们报道了微波辅助Ru（III）/ TBHP介导的吲哚与四甲基脲（TMU）合成对称以及不对称的双（吲哚基）甲烷的反应，其中TMU作为甲基化剂。这是第一个使用TMU作为亚甲基来源的报告。此外，本文还首次报道了通过使用碳前体合成不对称的双（吲哚基）甲烷。反应中使用各种取代的吲哚。与现有方法相比，该反应产率高并且完成时间短得多。
• Copper(ii)-catalyzed C–H (sp3) oxidation and C–N cleavage: synthesis of methylene-bridged compounds using TMEDA as a carbon source in water
  作者：Dan Zhao、Yue Wang、Min-Xue Zhu、Qi Shen、Lei Zhang、Yun Du、Jian-Xin Li

  DOI：10.1039/c3ra40695d

  日期：——

  A green, simple, and efficient protocol for the selective methylenation via CuCl2/oxygen-mediated C–H (sp3) oxidation and C–N cleavage using tetramethylethylenediamine (TMEDA) as a carbon source has been developed. The reactions were achieved in green solvent water under atmospheric conditions. The protocol exhibited a broad substrate scope including indoles, anilines, pyrroles and 1,3-dicarbonyls. Furthermore, two key intermediates of the reaction were successfully identified and the mechanism was explored.

  以四甲基乙二胺（TMEDA）为碳源，通过 CuCl2/氧气介导的 CâH (sp3) 氧化和 CâN 裂解进行选择性亚甲基化的绿色、简单而高效的方案已经开发出来。反应在大气条件下的绿色溶剂水中进行。该方案的底物范围很广，包括吲哚、苯胺、吡咯和 1,3-二羰基。此外，还成功鉴定了反应的两个关键中间体，并探索了反应机理。