3,3'-(phenylmethylene)bis(2-phenyl-1H-indole) | 35173-73-0

• 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'-(phenylmethylene)bis(2-phenyl-1H-indole)
• 英文别名: 1H-Indole, 3,3'-(phenylmethylene)bis[2-phenyl-；2-phenyl-3-[phenyl-(2-phenyl-1H-indol-3-yl)methyl]-1H-indole
• CAS: 35173-73-0
• 化学式: C₃₅H₂₆N₂
• 分子量: 474.605
• InChiKey: UIAOMZIJNOAZNB-UHFFFAOYSA-N

物化性质

• 熔点：
  266-268 °C
• 沸点：
  739.8±60.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  37
• 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：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 作用下， 生成 3,3'-(phenylmethylene)bis(2-phenyl-1H-indole)
  参考文献：
  名称：

  Burr; Gortner, Journal of the American Chemical Society, 1924, vol. 46, p. 1228

  摘要：

  DOI：

文献信息

• Phosphine‐Free Manganese(II)‐Catalyst Enables Acceptorless Dehydrogenative Coupling of Alcohols with Indoles
  作者：Vinita Yadav、Ekambaram Balaraman、Santosh B. Mhaske

  DOI：10.1002/adsc.202100621

  日期：2021.9.21

  molecularly defined NNN−Mn(II) pincer complex catalyzed acceptorless dehydrogenative coupling of alcohols with indoles is reported. A wide variety of symmetrical and unsymmetrical bis(indolyl)methane derivatives as well as some structurally important products such as Vibrindole A, Turbomycin B alkaloid, Antileukemic, and Anticancer agents were synthesized. Mechanistic studies illustrate the importance

  本文报道了一种空气稳定的、分子定义的 NNN-Mn(II) 钳形复合物催化醇与吲哚的无受体脱氢偶联。合成了多种对称和非对称双（吲哚基）甲烷衍生物以及一些结构上重要的产品，如 Vibrindole A、Turbomycin B 生物碱、抗白血病和抗癌剂。机理研究说明了 NH 部分在配合物中的重要性以及金属-配体合作在催化过程中的关键作用。
• Divergent Syntheses of Indoles and Quinolines Involving N1–C2–C3 Bond Formation through Two Distinct Pd Catalyses
  作者：Su San Jang、Young Ho Kim、So Won Youn

  DOI：10.1021/acs.orglett.0c02898

  日期：2020.12.4

  annulative couplings of 2-alkenylanilines with aldehydes using alcohols as both the solvent and hydrogen source have been developed. These domino processes allow divergent syntheses of two significant N-heterocycles, indoles and quinolines, from the same substrate by tuning reaction parameters, which seems to invoke two distinct mechanisms. The nature of the ligand and alcoholic solvent had a profound

  已经开发了使用醇作为溶剂和氢源的Pd催化的2-链烯基苯胺与醛的环状偶联。这些多米诺过程允许通过调节反应参数从同一底物上不同的合成两个重要的N杂环（吲哚和喹啉），这似乎调用了两种不同的机制。配体和醇溶剂的性质对这些方案的选择性和效率产生了深远的影响。尤其值得注意的是，吲哚的形成是通过克服两个重大挑战而实现的：烯烃的区域选择性加氢palpalpalation和随后的Csp 3 -Pd物种与反应性较低的亚胺之间的后续反应。
• An underrated cheap Lewis acid: Molecular bromine as a robust catalyst for bis(indolyl)methanes synthesis
  作者：Deqiang Liang、Wenzhong Huang、Lin Yuan、Yinhai Ma、Jingmei Ma、Deman Ning

  DOI：10.1016/j.catcom.2014.06.005

  日期：2014.10

  A discovery that inexpensive elemental bromine can act as a potent Lewis acid catalyst is disclosed. Under the catalysis of only 2 mol% of Br2, indoles reacted rapidly with carbonyl compounds to give bis(indolyl)methanes with extremely high efficiency and wide substrate scope. Moreover, a Br2-catalyzed aqueous-phase reaction is also presented to further demonstrate the power of this novel catalyst

  公开了廉价的元素溴可以用作有效的路易斯酸催化剂的发现。在仅2摩尔％的Br 2的催化下，吲哚与羰基化合物迅速反应，从而以极高的效率和宽泛的底物范围生成双（吲哚基）甲烷。此外，还提出了Br 2催化的水相反应，以进一步证明这种新型催化剂的功能。
• Synthesis of Spiro[indole-3,5′-isoxazoles] with Anticancer Activity via a Formal [4 + 1]-Spirocyclization of Nitroalkenes to Indoles
  作者：Alexander V. Aksenov、Dmitrii A. Aksenov、Nikolai A. Arutiunov、Nicolai A. Aksenov、Elena V. Aleksandrova、Zhenze Zhao、Liqin Du、Alexander Kornienko、Michael Rubin

  DOI：10.1021/acs.joc.9b00808

  日期：2019.6.7

  An acid-assisted [4 + 1]-cycloaddition of indoles with nitrostyrenes affords 4′H-spiro[indole-3,5′-isoxazoles] in a diastereomerically pure form. Several of these spirocyclic molecules exhibit promising anticancer activity by reducing viability and inducing differentiation of neuroblastoma cells.

  与硝基苯乙烯酸辅助[4 + 1] -环的吲哚，得到4' ħ -螺[吲哚-3,5'-异恶唑]在一个非对映异构纯的形式。这些螺环分子中的几种通过降低活力并诱导神经母细胞瘤细胞分化而显示出有希望的抗癌活性。
• Development of Transition‐Metal‐Free Lewis Acid‐Initiated Double Arylation of Aldehyde: A Facile Approach Towards the Total Synthesis of Anti‐Breast‐Cancer Agent
  作者：Sanjay Singh、Rina Mahato、Pragya Sharma、Naveen Yadav、Nagaraju Vodnala、Chinmoy Kumar Hazra

  DOI：10.1002/chem.202104545

  日期：2022.3.7

  reported. This protocol features mild conditions, feedstock reagents, very low catalyst loading, remarkable scope (>85 examples) and gram-scale synthesis (TON=475). Moreover, several unexplored biologically active molecules for example, the antiparkinson agent, vibrindole A, turbomycin B and, total synthesis of an anti-breast-cancer agent is demonstrated. Control experiments and mechanistic studies

  报道了一种用于合成对称/不对称三芳基甲烷和二芳基甲烷的无过渡金属方法。该协议具有温和的条件、原料试剂、极低的催化剂负载、显着的范围（>85 个示例）和克级合成（TON=475）。此外，还展示了几种未开发的生物活性分子，例如抗帕金森剂、vibrindole A、涡轮霉素 B 和抗乳腺癌剂的全合成。还进行了对照实验和机理研究，以检测反应中间体和反应进程，以阐明可能的反应机理。