5,5'-dimethoxy-3,3'-(thiophen-2-yl-methanediyl)bisindole | 1422180-07-1

• 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: 5,5'-dimethoxy-3,3'-(thiophen-2-yl-methanediyl)bisindole
• 英文别名: bis(5-methoxyindol-3-yl)(2-thienyl)methane；5-methoxy-3-[(5-methoxy-1H-indol-3-yl)-thiophen-2-ylmethyl]-1H-indole
• CAS: 1422180-07-1
• 化学式: C₂₃H₂₀N₂O₂S
• 分子量: 388.49
• InChiKey: JVJBTLCQVVRYER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 5-甲氧基吲哚 在 双(乙腈)氯化钯(II) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以80%的产率得到5,5'-dimethoxy-3,3'-(thiophen-2-yl-methanediyl)bisindole
  参考文献：
  名称：

  钯（II）在醛和烯酮的亲电子活化中：吲哚的有效C-3功能化

  摘要：

  在室温下，在空气/水分存在且没有任何其他酸/碱的情况下，ad 8过渡金属络合物PdCl 2（MeCN）2催化吲哚与醛和烯酮作为亲电子体的区域选择性C-3烷基化反应，添加剂或配体。在该烷基化反应中的活性催化剂是有机金属中间体C1，它是由吲哚与钯（II）预催化剂反应形成的。C1及其类似物与吲哚和代孕化合物的晶体学表征和反应性正在进行中。

  DOI：

  10.1016/j.tetlet.2015.08.080

文献信息

• Palladium(II) in electrophilic activation of aldehydes and enones: efficient C-3 functionalization of indoles
  作者：Swapna Sarita Mohapatra、Priyabrata Mukhi、Anuradha Mohanty、Satyanarayan Pal、Aditya Omprakash Sahoo、Debjit Das、Sujit Roy

  DOI：10.1016/j.tetlet.2015.08.080

  日期：2015.10

  The regioselective C-3 alkylation of indoles with aldehydes and enones as electrophiles is catalyzed by a d8 late transition metal complex PdCl2(MeCN)2 at room temperature in the presence of air/moisture and in the absence of any additional acid/base, additive, or ligand. The active catalyst in this alkylation is an organometallic intermediate C1 which is formed from the reaction of indole with the

  在室温下，在空气/水分存在且没有任何其他酸/碱的情况下，ad 8过渡金属络合物PdCl 2（MeCN）2催化吲哚与醛和烯酮作为亲电子体的区域选择性C-3烷基化反应，添加剂或配体。在该烷基化反应中的活性催化剂是有机金属中间体C1，它是由吲哚与钯（II）预催化剂反应形成的。C1及其类似物与吲哚和代孕化合物的晶体学表征和反应性正在进行中。
• Pd-catalyzed C–H activation in water: synthesis of bis(indolyl)methanes from indoles and benzyl alcohols
  作者：Hidemasa Hikawa、Yuusaku Yokoyama

  DOI：10.1039/c2ra21887a

  日期：——

  A method for the synthesis of bis(indolyl)methanes via palladium-catalyzed domino reactions of indoles with benzyl alcohols was developed. This protocol involves C3-benzylation of indoles and benzylic C–H functionalization in water.

  开发了一种通过钯催化的吲哚与苄醇的多米诺反应合成双（吲哚基）甲烷的方法。该协议涉及吲哚的C3-苄基化和苄基C–H的功能化。水。
• 10.1007/s00706-024-03215-2
  作者：Suresh, Muthiah、Singh, Raj Bahadur、Katlakunta, Sadhana、Patra, Snigdha Rani、Tanwer, Yogesh Bhaskar Singh、Mallick, Sadhucharan、Bhunia, Sabyasachi、Das, Debjit

  DOI：10.1007/s00706-024-03215-2

  日期：——

  A starch-supported cuprous iodide nanoparticles (CuI-NPs@starch) catalysed C–C bond cleaving reaction involving carbon-based leaving groups like malononitrile, ethyl cyanoacetate, acetylacetone, and Meldrum’s acid has been developed under moisture and air insensitive conditions. This competent C–C bond cleavage reaction is studied in detail as an attractive alternative method to synthesize biologically

  淀粉支撑的碘化亚铜纳米粒子 (CuI-NPs@starch) 催化 C-C 键断裂反应，涉及丙二腈、氰乙酸乙酯、乙酰丙酮和 Meldrum 酸等碳基离去基团，已在湿度和空气不敏感的条件下开发出来。这种有效的 C-C 键断裂反应作为一种有吸引力的替代方法被详细研究，以中等至良好的产率合成生物相关的双吲哚基甲烷。 CuI-NPs@starch 在水介质中合成，并通过 X 射线粉末衍射、扫描电子显微镜、能量色散 X 射线光谱研究进行表征。 图形概要
• Discovery of 3,3′-diindolylmethanes as potent antileishmanial agents
  作者：Sandip B. Bharate、Jaideep B. Bharate、Shabana I. Khan、Babu L. Tekwani、Melissa R. Jacob、Ramesh Mudududdla、Rammohan R. Yadav、Baljinder Singh、P.R. Sharma、Sudip Maity、Baldev Singh、Ikhlas A. Khan、Ram A. Vishwakarma

  DOI：10.1016/j.ejmech.2013.02.024

  日期：2013.5

  An efficient protocol for synthesis of 3,3'-diindolylmethanes using recyclable Fe-pillared interlayered clay (Fe-PILC) catalyst under aqueous medium has been developed. All synthesized 3,3'-diindolylmethanes showed promising antileishmanial activity against Leishmania donovani promastigotes as well as axenic amastigotes. Structure-activity relationship analysis revealed that nitroaryl substituted diindolylmethanes showed potent antileishmanial activity. The 4-nitrophenyl linked 3,3'-diindolylmethane 8g was found to be the most potent antileishmanial analog showing IC50 values of 7.88 and 8.37 mu M against both L donovani promastigotes and amastigotes, respectively. Further, a pharmacophore based QSAR model was established to understand the crucial molecular features of 3,3'-diindolylmethanes essential for potent antileishmanial activity. These compounds also exhibited promising antifungal activity against Cryptococcus neoformans, wherein fluorophenyl substituted 3,3'-diindolylmethanes were found to be most potent antifungal agents. Developed synthetic protocol will be useful for economical and eco-friendly synthesis of potent antileishmanial and antifungal 3,3'-diindolylmethane class of compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Utilization of flow chemistry in catalysis: New avenues for the selective synthesis of Bis(indolyl)methanes
  作者：Swapna S. Mohapatra、Zoe E. Wilson、Sujit Roy、Steven V. Ley

  DOI：10.1016/j.tet.2017.02.026

  日期：2017.4

  Flow chemistry enables the preparation of bis(indolyl)methanes from various indoles and structurally divergent aldehydes using Sc(OTf)3 catalysis. The reaction is regioselective for C-3 functionalization of the indoles, occurring over short reaction times allowing for rapid investigation of scope with straightforward work up facilitating product isolation.

  流动化学能够使用Sc（OTf）3催化从各种吲哚和结构不同的醛制备双（吲哚基）甲烷。该反应对吲哚的C-3功能化具有区域选择性，反应时间短，可以快速研究范围，并直接进行后处理，以利于产物分离。