3,3'-((4-nitrophenyl)methylene)bis(2-phenyl-1H-indole) | 1410720-17-0

• 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: 3,3'-((4-nitrophenyl)methylene)bis(2-phenyl-1H-indole)
• 英文别名: 3,3′-((4-nitrophenyl)methylene)bis(2-phenyl-1H-indole)；3-[(4-nitrophenyl)-(2-phenyl-1H-indol-3-yl)methyl]-2-phenyl-1H-indole
• CAS: 1410720-17-0
• 化学式: C₃₅H₂₅N₃O₂
• 分子量: 519.602
• InChiKey: MBINNZORZPLWAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 silver trifluoromethanesulfonate 、 silver trifluoroacetate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 3,3'-((4-nitrophenyl)methylene)bis(2-phenyl-1H-indole)
  参考文献：
  名称：

  Ag(I)-催化多米诺环化-加成序列，同时羰基和炔烃活化作为 2,2'-二取代双吲哚芳基甲烷的途径

  摘要：

  通过 Ag(I) 催化的环异构化和邻炔基苯胺和芳基醛上的脱氧加成序列，开发了一种在吲哚部分具有各种取代基的对称 3, 3'-双吲哚芳基甲烷的有效合成方法。Ag(I) 被提议同时激活炔烃单元和羰基部分，导致多米诺第一个 5 -endo-dig吲哚环化，除了 C=O，第二个吲哚环化，以及它的脱羟基加成。

  DOI：

  10.1021/acs.orglett.6b02321

文献信息

• A one-pot synthesis of 2,2′-disubstituted diindolylmethanes (DIMs) via a sequential Sonogashira coupling and cycloisomerization/C3-functionalization of 2-iodoanilines
  作者：Anirban Kayet、Vinod K. Singh

  DOI：10.1039/c7ob01701d

  日期：——

  A Pd(II)-Ag(I) catalyzed highly efficient synthesis of diindolylmethane has been developed. This transformation consists of a one pot sequential Sonogashira coupling (and desilylation) followed by cycloisomerization/C3-functionalization of 2‑iodoanilines. Six new bonds (four C-C and two C-N) are formed in one pot fashion. A variety of diindolylmethanes were obtained in excellent yields (up to 94%)

  已经开发了Pd（II）-Ag（I）催化的二吲哚基甲烷的高效合成。此转化过程包括一锅顺序的Sonogashira偶联（和去甲硅烷基化），然后进行2-碘苯胺的环异构化/ C3官能化。六个新债券（四个CC和两个CN）以一种底池形式形成。在温和的反应条件下，以优异的收率（高达94％）获得了各种二吲哚基甲烷，该策略也适用于克规模的合成。将产物转化为各种合成有用的化合物。
• Silver Nitrate Catalysed Tandem Reactions of O-Ethynylanilines with Aryl Aldehydes: Selective One-Pot Synthesis of Bis(Indolyl)Methanes
  作者：Bo-Lun Hu、Hua-Nan Hu、Ri-Yuan Tang

  DOI：10.3184/174751912x13394919935692

  日期：2012.8

  Bis(indolyl)methanes are an important class of indole derivatives that have been widely used in medical treatments. A novel silver nitrate-catalysed one-pot synthesis of bis(indolyl)methanes has been developed. In the presence of silver nitrate, cycloisomerisation and bis-addition of o-ethynylanilines with aromatic aldehydes were carried out efficiently to afford the corresponding bis(indolyl)methanes

  双（吲哚基）甲烷是一类重要的吲哚衍生物，已广泛用于医学治疗。已开发出一种新型硝酸银催化的双（吲哚基）甲烷一锅法合成。在硝酸银的存在下，邻乙炔苯胺与芳香醛的环异构化和双加成有效地以良好到极好的产率提供相应的双（吲哚基）甲烷。
• Acceleration under solvent-drop grinding: Synthesis of bis(indolyl)methanes using small amounts of organic solvents or ionic liquids
  作者：Kiyoshi Tanemura

  DOI：10.1016/j.tetlet.2021.153391

  日期：2021.10

  The reactions for the synthesis of bis(indolyl)methanes were accelerated by the addition of a few drops of solvents. Solvent effect for the addition of organic solvents and ionic liquids was examined. The yields of bis(indolyl)methanes increased by the addition of THF, 1-ethyl-3-ethylimidazolium bis(trifluoromethylsulfonyl)imide ([emim]NTf2), and 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim]PF6)

  通过添加几滴溶剂加速了合成双（吲哚基）甲烷的反应。检查了添加有机溶剂和离子液体的溶剂效应。通过添加 THF、1-乙基-3-乙基咪唑鎓双（三氟甲基磺酰基）亚胺 ([emim]NTf 2 ) 和 1-丁基-3-甲基咪唑鎓六氟磷酸盐 ([bmim]PF 6）。溶剂滴研磨方法对于“固体+液体”和“固体+固体”的反应非常有用。
• HOAc catalyzed three-component reaction for the synthesis of 3,3′-(arylmethylene)bis(1<i>H</i>-indoles)
  作者：Heng Li、Yan Zhu、Cong Jiang、Jia Wei、Ping Liu、Peipei Sun

  DOI：10.1039/d2ob00395c

  日期：——

  catalyzed three-component reaction of 2-(arylethynyl)anilines with arylaldehydes has been achieved, which leads to the generation of 3,3′-(arylmethylene)bis(1H-indoles) with good to excellent yields and high regioselectivity under transition-metal-free conditions. Four new C–C and C–N bonds were effectively formed in a one-pot procedure. Subsequent research on the reaction mechanism indicated that the

  已经实现了一种高效的 HOAc 催化的 2-(芳基乙炔基)苯胺与芳基醛的三组分反应，从而生成了具有良好至优异收率和高区域选择性的 3,3'-(芳基亚甲基)双(1 H-吲哚)在无过渡金属条件下。在一锅法中有效地形成了四个新的 C-C 和 C-N 键。随后对反应机理的研究表明，该反应可能涉及分子内环化和级联分子间脱水缩合过程。
• Well-dispersed sulfated zirconia nanoparticles as high-efficiency catalysts for the synthesis of bis(indolyl)methanes and biodiesel
  作者：Guochang Chen、Cun-Yue Guo、Hongbin Qiao、Mingfu Ye、Xiaoning Qiu、Caibo Yue

  DOI：10.1016/j.catcom.2013.07.006

  日期：2013.11

  Well-dispersed sulfated zirconia nanoparticles were synthesized with poly(N-vinylpyrrolidone) as a surfactant. The resultant sulfated zirconia nanoparticles are characterized by SEM, XRD, FT-IR and XPS. These nanoparticles were directly used as catalysts for the synthesis of bis(indolyl)methanes and biodiesel via electrophilic substitution reaction of indole with various aldehydes and the esterification of long-chain free fatty acids and exhibited excellent catalytic activity. The mechanism of the formation of the synthesized zirconia nanoparticles was also proposed. (C) 2013 Elsevier B.V. All rights reserved.