bis(2-phenyl-1H-indol-3-yl)methane | 50615-06-0

• 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: bis(2-phenyl-1H-indol-3-yl)methane
• 英文别名: 2,2'-Diphenyl-3,3'-diindolyl-methan；Bis(2-phenylindol-3-yl)methane；2-phenyl-3-[(2-phenyl-1H-indol-3-yl)methyl]-1H-indole
• CAS: 50615-06-0
• 化学式: C₂₉H₂₂N₂
• 分子量: 398.507
• InChiKey: IJCZAAWBSMXPEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  184.5 °C
• 沸点：
  696.3±55.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• 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

• 作为反应物：
  描述：

  bis(2-phenyl-1H-indol-3-yl)methane 、 β-环糊精 以 甲醇 、 aq. phosphate buffer 为溶剂， 生成
  参考文献：
  名称：

  Studies on aqueous solubility of 3,3′-diindolylmethane derivatives using cyclodextrin inclusion complexes

  摘要：

  The supramolecular interaction of 3,3'-diindolylmethane (DIM) and its derivatives with alpha-, beta-, and gamma-cyclodextrins (CDs) has been investigated to improve their aqueous solubility. A series of complexes of alpha-, beta-, and gamma-CDs with DIMs were prepared and their inclusion complexation behavior in solution phase assessed by fluorescence, UV-visible spectroscopy and circular dichroism. Circular dichroism spectra revealed that incorporation of DIMs in the chiral environment of the CDs affecting their electric transitions leading to the development of induced circular dichroism bands in the near UV region. A linear increase of aqueous solubility of DIMs in presence of CDs was observed from their phase-solubility diagrams indicating the formation of soluble inclusion complexes. According to the continuous variation method a 1:1 stoichiometry has been proposed for DIM cyclodextrins complexes. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.09.036
• 作为产物：
  描述：

  2-苯基吲哚-3-甲醛 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 bis(2-phenyl-1H-indol-3-yl)methane
  参考文献：
  名称：

  2-苯基吲哚和咔唑的衍生物作为磷光有机发光二极管的主体材料

  摘要：

  报道了咔唑和2-苯基吲哚的衍生物的合成及其热，电化学，光物理和电荷传输性质。强调具有反应性官能团的化合物。两种化合物形成分子玻璃，其玻璃化转变温度为57°C和134°C。合成的化合物吸收200-375 nm范围内的电磁辐射，并发射350-550 nm范围内的辐射。他们的解决方案显示斯托克斯位移高达81 nm。发现它们的三重态能级范围为2.88–3.04 eV。发现合成化合物的电离电势为5.45eV至5.88eV。通过ATR-FTIR光谱法证明了合成单体在固态中的光聚合能力。通过空间电荷限制电流（SCLC）方法研究了电荷传输性质。零场空穴迁移率达到1.97×10-5 厘米2个 V -1小号-1观察到。根据表征结果，选择了两种化合物作为蓝色和绿色磷光有机发光二极管的主体进行研究。由铟锡氧化物阳极，空穴传输层，带有3-（（1-（4-乙烯基苄基）-2-苯基-1 H-吲哚-3-基）甲基）-9-乙基的发光层组成的最佳制造器件-9

  DOI：

  10.1016/j.dyepig.2016.09.038

文献信息

• InCl₃-HMTA as a Methylene Donor: One-Pot Synthesis of Diindolylmethane (DIM) and Its Derivatives
  作者：Parasuraman Jaisankar、Prasun K. Pradhan、Sumit Dey、Venkatachalam Sesha Giri

  DOI：10.1055/s-2005-869897

  日期：——

  Treatment of indoles 1a-k with hexamethylenetetramine (HMTA) (2) in presence of a catalytic amount (10 mol%) of InCl3 resulted in 3,3′-diindolylmethane (DIM) derivatives 3a-k in excellent yields.

  将吲哚1a-k与六亚甲基四胺（HMTA）（2）在催化剂铟氯化物（InCl3，10摩尔%）存在下反应，得到了3,3′-二吲哚基甲烷（DIM）衍生物3a-k，产率极高。
• Vanadyl Acetylacetonate Catalyzed Methylenation of Imidazo[1,2-<i>a</i>]pyridines by Using Dimethylacetamide as a Methylene Source: Direct Access to Bis(imidazo[1,2-<i>a</i>]pyridin-3-yl)methanes
  作者：Pinku Kaswan、Nitesh Kumar Nandwana、Brenton DeBoef、Anil Kumar

  DOI：10.1002/adsc.201600225

  日期：2016.6.30

  imidazo[1,2‐a]pyridines using dimethylacetamide (DMA) as methylene source in the presence of vanadyl acetylacetonate [VO(acac)2] as the catalyst and iodobenzene diacetate as the oxidant. The reaction involves coupling of sp3‐ and sp2‐hybridized carbons and proceeds through the formation of an iminium ion. A wide variety of imidazo[1,2‐a]pyridines were converted to bis(imidazo[1,2‐a]pyridin‐3‐yl)methanes

  已经开发了一种有效的方案，用于在乙酰丙酮氧钒[VO（acac）2 ]为催化剂和碘代乙酸二苯酯为氧化剂的情况下，使用二甲基乙酰胺（DMA）作为亚甲基来源的咪唑并[1,2- a ]吡啶的甲基化。该反应涉及sp 3-和sp 2-杂化碳的偶合，并通过形成亚胺离子进行。多种咪唑并[1,2一]吡啶转化为双（咪唑并[1,2一]吡啶-3-基）甲烷在良好至优异的产量。克级反应证明了放大工艺的潜力。
• Radical intermediates in the peroxidation of indoles
  作者：Paola Astolfi、Lucedio Greci、Corrado Rizzoli、Paolo Sgarabotto、Giancarlo Marrosu

  DOI：10.1039/b102915k

  日期：——

  2-Substituted and 1,2-disubstituted indoles react with m-chloroperbenzoic acid and hydrogen peroxide in the presence of acid or calcium chloride affording 2- and 3-(3-oxoindol-2-yl)indoles; whereas 2,3-disubstituted indoles, reacting with the same oxidants, lead to the formation of products typical of pentaatomic ring opening. The reaction mechanisms are discussed in terms of electron transfer processes based on the redox potentials of the reagents, the Marcus theory and the reaction products distribution. The reactions of 1-hydroxy-2-phenylindole, which yield 2-phenylisatogen (2-phenyl-3-oxo-3H-indole 1-oxide), bisnitrone and 3-(3-oxoindol-2-yl)indole are also explained by an electron transfer mechanism depending on the oxidant and on the conditions of the reaction. The structures of 2- and 3-(3-oxoindol-2-yl)indoles have been elucidated by X-ray analysis.

  2-取代和1,2-二取代吲哚在酸或氯化钙存在下与间氯过苯甲酸和过氧化氢反应，得到2-和3-(3-氧代吲哚-2-基)吲哚；而2,3-二取代吲哚与相同的氧化剂反应，会形成典型的五原子开环产物。基于试剂的氧化还原电位、Marcus 理论和反应产物分布，从电子转移过程的角度讨论了反应机理。还解释了 1-羟基-2-苯基吲哚的反应，产生 2-苯基 isatogen (2-苯基-3-氧代-3H-吲哚 1-氧化物)、双硝酮和 3-(3-氧代吲哚-2-基)吲哚通过取决于氧化剂和反应条件的电子转移机制。 2-和3-(3-氧代吲哚-2-基)吲哚的结构已通过X射线分析阐明。
• Lewis Acid-Promoted Typical Friedel–Crafts Reactions Using DMSO as a Carbon Source
  作者：Nagaraju Vodnala、Sanjay Singh、Chinmoy Kumar Hazra

  DOI：10.1021/acs.joc.2c01037

  日期：2022.8.5

  This study reports a mild and efficient synthetic protocol for the synthesis of symmetrical and unsymmetrical diarylmethanes (DAMs). Using DMSO as the C1 source and TMSOTf as the Lewis acid promoter, a series of functionalized symmetrical and unsymmetrical DAMs were synthesized in high yields. Gratifyingly, DMSO plays a dual role as a solvent and a C1 source and can also be replaced with its deuterated

  本研究报告了一种用于合成对称和不对称二芳基甲烷 (DAM) 的温和有效的合成方案。使用 DMSO 作为 C 1源和 TMSOTf 作为路易斯酸促进剂，以高产率合成了一系列功能化的对称和非对称 DAM。令人欣慰的是，DMSO 作为溶剂和 C 1源具有双重作用，并且还可以用其氘代对应物 DMSO- d 6代替，从而能够掺入 -CD 2部分进入二芳基甲烷骨架。所开发的方法已应用于具有各种官能团的各种底物，该协议也已扩展到使用普通原料化合物合成抗乳腺癌剂和抗凝剂。此外，已通过对照实验明确证明了假设的机制。
• Discovery of the Quinoxalinone–B(C₆F₅)₃·H₂O Combo as a Photocatalyst by Acidochromism Strategy: Aerobic Oxidation of Alcohol, Alkene, and Thiols
  作者：Jie Huang、Yun-Xuan Luo、Long Wang、Xiang-Ying Tang

  DOI：10.1021/acs.orglett.3c01977

  日期：2023.8.4

  convenient strategy for catalyst designation. Herein, we reported that upon the addition of B(C6F5)3·H2O, the oxidation potential of quinoxalinone increased remarkably, enabling the photoredox aerobic oxidation of alcohol, thiols, and alkenes toward carbonyl compounds and dithioethers under visible light conditions. Mechanistic studies, including X-ray structure analysis, cyclic voltammetry, electron paramagnetic

  通过分子间相互作用改变光催化剂反应性代表了一种简单而方便的催化剂设计策略。在此，我们报道了添加B(C 6 F 5 ) 3 ·H 2 O后，喹喔啉酮的氧化电位显着增加，使得醇、硫醇和烯烃在可见光下发生光氧化还原有氧氧化，生成羰基化合物和二硫醚。状况。包括X射线结构分析、循环伏安法、电子顺磁共振测量、紫外可见吸收和荧光光谱在内的机理研究表明，喹喔啉酮-B(C 6 F 5 ) 3 ·H 2 O组合可以作为一种多功能的组合物。用于能量转移和单电子转移过程的光催化剂。