3,3'-((3-hydroxy-4-methoxyphenyl)methylene)-bis(1H-indole)

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,3'-((3-hydroxy-4-methoxyphenyl)methylene)-bis(1H-indole)
• 英文别名: 3,3'-(4-methoxy-3-hydroxyphenylmethanediyl)bisindole；5-[bis(1H-indol-3-yl)methyl]-2-methoxyphenol
• 化学式: C₂₄H₂₀N₂O₂
• mdl: MFCD03080300
• 分子量: 368.435
• InChiKey: CWMPUSKUSXTPAT-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：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  异香兰素 、 吲哚 在 L-proline-silica modified Fe₃O₄ nanoparticle 作用下， 以 水 为溶剂， 反应 1.0h， 以81%的产率得到3,3'-((3-hydroxy-4-methoxyphenyl)methylene)-bis(1H-indole)
  参考文献：
  名称：

  l-Proline-modified magnetic nanoparticles (LPMNP): a novel magnetically separable organocatalyst

  摘要：

  这项研究为稳定磁性纳米粒子上的 L-脯氨酸部分提供了一种新的有效方法，以制备用于有机转化的新型磁性可回收有机催化剂。在吲哚和醛在水中合成双(吲哚基)甲烷的缩合反应中评估了这种多相有机催化剂的催化活性。

  DOI：

  10.1039/c4ra01121j

文献信息

• One dimensional CdS nanostructures: heterogeneous catalyst for synthesis of aryl-3,3′-bis(indol-3-yl)methanes
  作者：Prakash K. Chhattise、Sudhir S. Arbuj、Kakasaheb C. Mohite、Sanjay V. Bhavsar、Amit S. Horne、Kalpana N. Handore、Vasant V. Chabukswar

  DOI：10.1039/c4ra03419h

  日期：——

  Herein, we have developed a novel heterogeneous catalytic system for synthesis of bis(indol-3-yl)methanes using one dimensional (1D) CdS nanorods. CdS nanorods were synthesized by a solvothermal reaction technique at 200 °C over 12 h in the presence of ethylenediamine as a solvent. The prepared 1D CdS was characterized using various spectroscopic methods. X-ray diffraction (XRD) revealed the formation of highly crystalline CdS having a wurtzite structure. FESEM analysis confirms the formation of a rod like morphology with length around 150 to 200 nm and diameter ∼15 nm. TEM also validates the formation of uniform size one dimensional (1D) CdS nanostructures. The catalytic activity of 1D CdS as a Lewis acid was investigated for the synthesis of bis(indol-3-yl)methanes (BIMs) with various substituted aldehydes and indoles within shorter reaction time affording the corresponding product in excellent yield.

  在此，我们开发了一种新型异质催化系统，用于合成双(吲哚-3-基)甲烷，采用了一维(1D) CdS纳米棒。CdS纳米棒是通过在200°C下，使用乙二胺作为溶剂进行12小时的溶剂热反应合成的。制备的1D CdS采用了多种光谱方法进行了表征。X射线衍射(XRD)显示出高结晶性的CdS形成了闪锌矿结构。场发射扫描电子显微镜(FESEM)分析确认了纳米棒状形貌的形成，其长度约为150至200纳米，直径约为15纳米。透射电子显微镜(TEM)也验证了均匀尺寸的一维(1D) CdS纳米结构的形成。作为路易斯酸的1D CdS的催化活性被研究用于与各种取代醛和吲哚在较短反应时间内合成双(吲哚-3-基)甲烷(BIMs)，并获得了优异的产率。
• Expeditious, Mild and Solvent Free Synthesis of Bis(indolyl)methanes, Using a Mixture of Phosphorus Pentoxide in Methanesulphonic Acid
  作者：Amulrao U. Borse、Mahesh N. Patil、Nilesh L. Patil

  DOI：10.1155/2012/637536

  日期：——

  Highly rapid and efficient synthesis of Bis(indolyl)methanes has been developed by using a mixture of phosphorus pentoxide in methanesulphonic acid (Eaton’s reagent) at ambient temperature under solvent free condition.

  已经开发出一种高度快速和高效的双吲哚甲烷合成方法，该方法使用磷五氧化物与甲磺酸（伊顿试剂）的混合物，在常温下无溶剂条件下进行。
• Synthesis and characterization of Polyindole and its catalytic performance study as a heterogeneous catalyst
  作者：PRAKASH CHHATTISE、KALPANA HANDORE、AMIT HORNE、KAKASAHEB MOHITE、ATUL CHASKAR、SABRINA DALLAVALLE、VASANT CHABUKSWAR

  DOI：10.1007/s12039-016-1040-1

  日期：2016.3

  The catalytic performance study of polyindole as a heterogeneous catalyst is reported for the synthesis of 3,3’-arylmethylene-bis-1H-Indole derivatives using various substituted aldehydes and indole under reflux reaction condition with good to excellent yield. Polyindole was synthesized by chemical oxidative polymerization using citric acid as a dopant. The synthesized polymer was well characterized by various spectroscopic techniques like FT-IR, XRD, FESEM, etc. The XRD pattern confirms the partially crystalline nature of polyindole. The FESEM images of polyindole revealed the formation of irregularly shaped particulate nature with size in the range of 0.2 to 6 micron. In FT-IR spectrum, the major peak at ∼ 3400 cm−1 indicates N-H stretching and at 1564 −1624 cm −1 indicates C-C stretching of benzenoid ring of indole. The presence of peak at ∼ 3400 cm−1 indicates that the polymerization does not occur at nitrogen. The present protocol has certain advantages like recyclability, low loading of the catalyst, low-cost and efficient use of polyindole as a heterogeneous catalyst.

  报告了聚吲哚作为异相催化剂在回流反应条件下合成3,3'-芳基亚甲基-双1H-吲哚衍生物的催化性能研究，使用了多种取代醛和吲哚，获得了良好到优异的产率。聚吲哚是通过化学氧化聚合合成的，使用柠檬酸作为掺杂剂。合成的聚合物通过FT-IR、XRD、FESEM等多种光谱技术进行了良好的表征。XRD图谱确认了聚吲哚的部分结晶特性。FESEM图像显示聚吲哚形成了不规则形状的颗粒，尺寸范围为0.2到6微米。在FT-IR光谱中，约3400 cm−1处的主要峰指示N-H伸展，1564-1624 cm−1处的峰则指示吲哚苯环的C-C伸展。约3400 cm−1处的峰的存在表明聚合未发生在氮上。本协议具有一些优点，如可重复使用、催化剂负载量低、成本低以及聚吲哚作为异相催化剂的高效利用。
• ELECTROPHILIC SUBSTITUTION OF INDOLES CATALYZED BY TRIPHENYL PHOSPHONIUM PERCHLORATE: SYNTHESIS OF 3-ACETYL INDOLES AND <i>BIS</i>-INDOLYLMETHANE DERIVATIVES
  作者：Rajagopal Nagarajan、Paramasivan T. Perumal

  DOI：10.1081/scc-120001515

  日期：2002.1.1

  ABSTRACT Triphenyl phosphonium perchlorate (TPP) is found to catalyze the acetylation of indoles with acetic anhydride to give 3-acetyl indoles. Similarly bis-indolylmethane derivatives were prepared by the electrophilic substitution reaction of indole with substituted benzaldehydes.

  摘要 高氯酸三苯鏻 (TPP) 被发现可催化吲哚与乙酸酐的乙酰化反应，生成 3-乙酰吲哚。类似地，双吲哚甲烷衍生物是通过吲哚与取代苯甲醛的亲电取代反应制备的。
• 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.