5,5'-dimethoxy-3,3'-(naphth-1-yl-methanediyl)bisindole | 1442639-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,5'-dimethoxy-3,3'-(naphth-1-yl-methanediyl)bisindole
• 英文别名: 3,3'-(naphthalen-1-ylmethylene)bis(5-methoxy-1H-indole)；5-methoxy-3-[(5-methoxy-1H-indol-3-yl)-naphthalen-1-ylmethyl]-1H-indole
• CAS: 1442639-72-6
• 化学式: C₂₉H₂₄N₂O₂
• 分子量: 432.522
• InChiKey: COYDRIPGASZWIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  50
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 1-萘甲醛 在 双(乙腈)氯化钯(II) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.0h， 以96%的产率得到5,5'-dimethoxy-3,3'-(naphth-1-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。
• 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.
• Tetranuclear Zn/4f coordination clusters as highly efficient catalysts for Friedel–Crafts alkylation
  作者：Kieran Griffiths、Prashant Kumar、Geoffrey R. Akien、Nicholas F. Chilton、Alaa Abdul-Sada、Graham J. Tizzard、Simon J. Coles、George E. Kostakis

  DOI：10.1039/c6cc03608b

  日期：——

  A series of custom-designed high yield isoskeletal tetranuclear 3d/4f coordination clusters showing high efficiency as catalysts with low catalytic loadings in Friedel Crafts alkylation are described for the first time....

  首次描述了一系列定制设计的高收率等骨架四核3d / 4f配位簇，这些化合物在弗里德尔工艺烷基化反应中作为低催化负载的催化剂表现出了高效率。