1,1-dimethyl-1,1-bis(3’-indolyl)-1-(p-hydroxyphenyl)methane

• 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: 1,1-dimethyl-1,1-bis(3’-indolyl)-1-(p-hydroxyphenyl)methane
• 英文别名: 1,1'-dimethyl-1,1-bis(3-indolyl)-1-(p-hydroxyphenyl)methane；4-(bis(1-methyl-1H-indol-3-yl)methyl)phenol；4-[bis(1-methyl-1H-3-indolyl)methyl]phenol；4-[Bis(1-methylindol-3-yl)methyl]phenol
• 化学式: C₂₅H₂₂N₂O
• 分子量: 366.462
• InChiKey: MWLBYSOSFROPIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-dimethyl-1,1-bis(3’-indolyl)-1-(p-hydroxyphenyl)methane 在 potassium carbonate 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 4-[5-[4-[bis(1-methyl-1H-3-indolyl)methyl]-phenoxymethyl]-1,3,4-oxadiazol-2-yl]phenol
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,3,4-oxadiazole-linked bisindole derivatives as anticancer agents

  摘要：

  A series of ten 1,3,4-oxadiazole-linked bisindole derivatives have been synthesized. All compounds were evaluated for anticancer activity against four human cancer cell lines (MCF-7, KB, Colo-205, and A-549). Most of these new compounds exhibited significant anticancer activity as compared to etoposide. Compounds' GI(50) values range from < 0.1 to 3.9 mu M, while the positive control etoposide has a GI(50) in the range of 0.13-3.08 mu M in the cell lines employed. Among them, four compounds showed a higher activity than etoposide.

  DOI：

  10.1007/s00706-015-1448-1
• 作为产物：
  描述：

  3,3'-[(4-methoxyphenyl)methylene]bis(1-methyl-1H-indole) 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到1,1-dimethyl-1,1-bis(3’-indolyl)-1-(p-hydroxyphenyl)methane
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,3,4-oxadiazole-linked bisindole derivatives as anticancer agents

  摘要：

  A series of ten 1,3,4-oxadiazole-linked bisindole derivatives have been synthesized. All compounds were evaluated for anticancer activity against four human cancer cell lines (MCF-7, KB, Colo-205, and A-549). Most of these new compounds exhibited significant anticancer activity as compared to etoposide. Compounds' GI(50) values range from < 0.1 to 3.9 mu M, while the positive control etoposide has a GI(50) in the range of 0.13-3.08 mu M in the cell lines employed. Among them, four compounds showed a higher activity than etoposide.

  DOI：

  10.1007/s00706-015-1448-1

文献信息

• <i>N</i> ‐bromosuccinimide catalyzed condensations of indoles with carbonyl compounds under solvent‐free conditions
  作者：Hideko Koshima、Wataru Matsusaka

  DOI：10.1002/jhet.5570390539

  日期：2002.9

  NBS was found to be an efficient catalyst for condensations of indoles with aldehydes or ketones in the absence of solvent.

  人们发现，在没有溶剂的情况下，NBS是吲哚与醛或酮缩合的有效催化剂。
• Eutectic salts promote green synthesis of bis(indolyl) methanes
  作者：Najmadin Azizi、Zohreh Manocheri

  DOI：10.1007/s11164-011-0479-4

  日期：2012.9

  A convenient and rapid method for the electrophilic substitution reaction of indoles with carbonyl compounds has been developed by using deep eutectic solvent as green and reusable catalysts to afford the corresponding bis(indolyl) methanes in excellent yields at room temperature under mild reaction conditions.

  一种方便快捷的吲哚与羰基化合物的电嗅取代反应方法已经被开发，使用深共熔溶剂作为绿色可重复使用的催化剂，在温和反应条件下常温下获得相应的双（吲哚基）甲烷，产率极高。
• One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles
  作者：Jiachen Xiang、Jungang Wang、Miao Wang、Xianggao Meng、Anxin Wu

  DOI：10.1039/c5ob00025d

  日期：——

  This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products.

  本文描述了氨基酸与吲哚的脱羧脱氨双偶联反应，形成BIM骨架，并进一步应用于天然产物的一锅式全合成。
• Synthesis of Bis(indolyl)methane Derivatives Catalyzed by Recyclable Nano Fe3O4@ZrO2/SO4 2-
  作者：Hossein Ghafuri、Behnaz Ghorbani、Hamid Reza Esmaili Zand

  DOI：10.2174/1570178614666170707151649

  日期：2018.3.9

  synthesized Fe3O4@ZrO2/SO4 2- as a heterogeneous nanocatalyst and used it in one pot reaction of aldehyde and indole to obtain bis(indolyl)methane derivatives. Results: An effective method for the synthesis of bis(indolyl)methane derivatives in high yields was developed by the use of Fe3O4@ZrO2/SO4 2- as a catalyst. The synthesis of bis(indolyl)methane by this catalysts resulted in short reaction times and

  背景：双（吲哚基）甲烷衍生物具有多种生物学和药理特性，例如抗菌和抗血管生成活性，可作为细胞毒性剂和肿瘤生长抑制剂。已经报道了双（吲哚基）甲烷合成的几种方法，其中大多数涉及在质子酸或路易斯酸存在下吲哚与醛或酮的缩合。在该反应中还使用了诸如酶的其他催化剂，这些催化剂没有导致高收率。尽管如此，通过更好的方法来修改此反应还有很长的路要走。 方法：由于大量使用磁性硫酸盐氧化锆作为催化剂，我们决定研究其合成双（吲哚基）甲烷衍生物的能力。在这项工作中，为了提高收率并缩短反应时间，我们合成了Fe3O4 @ ZrO2 / SO4 2-作为非均相纳米催化剂，并将其用于醛和吲哚的一锅反应中，获得了双（吲哚基）甲烷衍生物。 结果：以Fe3O4 @ ZrO2 / SO42-为催化剂，开发了一种高产率合成双（吲哚基）甲烷衍生物的有效方法。用该催化剂合成双（吲哚基）甲烷可缩短反应时间，提高产率。这些类型催化剂的优点是易
• FeCl₃·6H₂O as a Mild Catalyst for Nucleophilic Substitution of Symmetrical Bis(indoyl)methanes
  作者：Chayamon Chantana、Jaray Jaratjaroonphong

  DOI：10.1021/acs.joc.0c02466

  日期：2021.2.5

  In this paper, unsymmetrical bis(indolyl)methane (BIM) and 3-alkylindole derivatives are smoothly synthesized from symmetrical BIMs with a variety of nucleophiles including heteroaromatic/aromatic compounds, allylsilane and alkynylsilane. FeCl3·6H2O is found to be a mild and highly effective catalyst for this nucleophilic substitution reaction in which N-methyl-2-phenylindole behaves as a good leaving

  在本文中，不对称双（吲哚基）甲烷（BIM）和3-烷基吲哚衍生物是由具有各种亲核试剂（包括杂芳族/芳族化合物，烯丙基硅烷和炔基硅烷）的对称BIM平稳合成的。FeCl 3 ·6H 2 O被发现是这种亲核取代反应的温和高效催化剂，其中N-甲基-2-苯基吲哚在C sp 3 -C sp 2键断裂反应中表现为良好的离去基团。操作简便，廉价且对环境友好的催化剂，温和的反应条件，宽泛的官能团耐受性和该反应策略的可扩展性是本方法的优点。