bis(6-chloroindol-3-yl)(phenyl)methane | 1234177-52-6

• 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(6-chloroindol-3-yl)(phenyl)methane
• 英文别名: 3,3'-(phenylmethylene)bis(6-chloro-1H-indole)；6-chloro-3-[(6-chloro-1H-indol-3-yl)-phenylmethyl]-1H-indole
• CAS: 1234177-52-6
• 化学式: C₂₃H₁₆Cl₂N₂
• 分子量: 391.299
• InChiKey: XCAZWIBCRMPFLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  6-氯吲哚 、 N,N-二乙基苄胺 在 叔丁基过氧化氢 、 copper(I) bromide 作用下， 以 癸烷 为溶剂， 反应 18.0h， 以65%的产率得到bis(6-chloroindol-3-yl)(phenyl)methane
  参考文献：
  名称：

  CuBr-catalyzed selective oxidation of N-azomethine: highly efficient synthesis of methine-bridged bis-indole compounds

  摘要：

  据报道，在叔丁基过氧化氢（TBHP）介导的 N-苄胺与吲哚的氧化交叉脱氢偶联（CDC）反应中，CuBr 催化了 C-N 键的高效裂解。在优化的反应条件下，成功合成了一系列甲基桥联双吲哚衍生物。

  DOI：

  10.1039/c004213g

文献信息

• Magnetically recyclable CuFe2O4 catalyst for efficient synthesis of bis(indolyl)methanes using indoles and alcohols under mild condition
  作者：Ngoc-Khanh Nguyen、Minh-Tuan Ha、Hoang Yen Bui、Quang Thang Trinh、Bich Ngoc Tran、Van Tuyen Nguyen、Tran Quang Hung、Tuan Thanh Dang、Xuan Hoan Vu

  DOI：10.1016/j.catcom.2020.106240

  日期：2021.1

  Bis(3-indolyl)methanes (BIM) are highly valuable and appear in the core structure of many natural products and pharmacologically active compounds (anticancer, anti-inflammatory, antiobesity, antimetastatic, antimicrobial, etc.). Herein, we have disclosed an air stable and highly efficient CuFe2O4 heterogeneous catalyst for alkylation of indoles with alcohols to give bis(3-indolyl)methanes in very good

  双（3-吲哚基）甲烷（BIM）具有很高的价值，并出现在许多天然产物和药理活性化合物（抗癌，抗炎，抗肥胖，抗肿瘤，抗微生物等）的核心结构中。在此，我们已经公开了一种空气稳定且高效的CuFe 2 O 4非均相催化剂，用于用醇将吲哚烷基化以非常好的收率得到双（3-吲哚基）甲烷。已经发现CuFe 2 O 4催化剂被磁循环至少五次而不会损失明显的催化活性。
• An underrated cheap Lewis acid: Molecular bromine as a robust catalyst for bis(indolyl)methanes synthesis
  作者：Deqiang Liang、Wenzhong Huang、Lin Yuan、Yinhai Ma、Jingmei Ma、Deman Ning

  DOI：10.1016/j.catcom.2014.06.005

  日期：2014.10

  A discovery that inexpensive elemental bromine can act as a potent Lewis acid catalyst is disclosed. Under the catalysis of only 2 mol% of Br2, indoles reacted rapidly with carbonyl compounds to give bis(indolyl)methanes with extremely high efficiency and wide substrate scope. Moreover, a Br2-catalyzed aqueous-phase reaction is also presented to further demonstrate the power of this novel catalyst

  公开了廉价的元素溴可以用作有效的路易斯酸催化剂的发现。在仅2摩尔％的Br 2的催化下，吲哚与羰基化合物迅速反应，从而以极高的效率和宽泛的底物范围生成双（吲哚基）甲烷。此外，还提出了Br 2催化的水相反应，以进一步证明这种新型催化剂的功能。
• One-pot three-component synthesis of bis(indolyl)methanes under solvent-free condition using heteropoly-11-tungsto-1-vanadophosphoric acid supported on natural clay as catalyst
  作者：Karuppaiah Selvakumar、Thangamariyappan Shanmugaprabha、Ramamoorthy Annapoorani、Ponnusamy Sami

  DOI：10.1080/00397911.2017.1296159

  日期：2017.5.3

  ABSTRACT One-pot three-component condensation reaction of two moles of indole and one mole of aromatic aldehyde for the synthesis of bis(indolyl)methanes in the presence of new catalytic material, heteropoly-11-tungsto-1-vanadophosphoric acid, H4[PVVW11O40] (HPV) supported on activated natural clay under solvent-free reaction condition has been proposed. The catalysts were prepared by incipient wetness

  摘要 在新型催化材料、杂多-11-钨-1-钒磷酸、H4[ ] 存在下，2 摩尔吲哚和 1 摩尔芳香醛的一锅三组分缩合反应合成双（吲哚基）甲烷。 PVVW11O40] (HPV) 在无溶剂反应条件下负载在活性天然粘土上。催化剂采用初湿浸渍法制备。还讨论了支持在天然粘土 (HPVAC-20) 上的 HPV (20%) 的物理化学特征。该方案的优点是无溶剂非均相反应条件、后处理程序简单、反应时间短、产物收率高、催化剂可重复使用。图形概要
• Graphene oxide: An efficient recyclable solid acid for the synthesis of bis(indolyl)methanes from aldehydes and indoles in water
  作者：Yihong Wang、Rui Sang、Yang Zheng、Li Guo、Mei Guan、Yong Wu

  DOI：10.1016/j.catcom.2016.09.027

  日期：2017.1

  An efficient synthesis of bis(indolyl)methanes from aldehydes with indoles through graphene oxide -catalyzed Friedel-Crafts alkylation is developed. The reaction proceeds in water by using graphene oxide as the single catalyst to provide the desired products in good to excellent yields. Also, this methodology has a broad substrate scope, and is environment friendly and cost economic.

  开发了一种通过氧化石墨烯催化的Friedel-Crafts烷基化反应从醛类和吲哚类化合物高效合成双（吲哚基）甲烷的方法。通过使用氧化石墨烯作为单一催化剂，该反应在水中进行，以良好至优异的产率提供所需的产物。而且，该方法具有广泛的衬底范围，并且是环境友好的和成本经济的。
• Meldrum's acid-induced and FeCl₃-catalyzed one-pot domino reactions for construction of bis(indolyl)methanes
  作者：Chenli Fan、Ruxue Li、Jiahui Duan、Keke Xu、Yanan Liu、Demao Wang、Xinwei He

  DOI：10.1080/00397911.2022.2076245

  日期：2022.4.18

  Abstract An eco-friendly and efficient Meldrum's acid-induced and FeCl3-catalyzed domino reactions of aromatic aldehydes and indoles for the formation of 3,3′-bis(indolyl)methanes has been developed. The present strategy features with inexpensive catalyst, green solvent, mild conditions, good functional group tolerance, and gram-scale synthesis. The transformation proceeded by a domino esterification

  摘要 开发了一种环保且高效的 Meldrum 酸诱导和 FeCl 3催化的芳香醛和吲哚多米诺反应，用于形成 3,3'-双（吲哚基）甲烷。本策略具有催化剂廉价、溶剂绿色、条件温和、官能团耐受性好和克级合成的特点。转化通过多米诺酯化、Knoevenagel 缩合、1,2-加成、消除和随后的 1,4-共轭加成过程进行。