3,3-Diphenylindoline | 40863-31-8

• 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-Diphenylindoline
• 英文别名: 3,3-Diphenyl-1,2-dihydroindole
• CAS: 40863-31-8
• 化学式: C₂₀H₁₇N
• 分子量: 271.362
• InChiKey: FGKHEUKMYOSVFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3-二苯基-1H-吲哚-2-硫酮 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以33%的产率得到3,3-Diphenylindoline
  参考文献：
  名称：

  吲哚啉-2-硫酮的光化学脱硫制取吲哚的新途径

  摘要：

  在胺存在下二氢吲哚-2-硫酮的光化学反应产生脱硫产物二氢吲哚。

  DOI：

  10.1039/c39880000572

文献信息

• Reduction of Indolin-2-ones and Desulfurization of Indoline-2-thiones to Indoline and Indole Derivatives
  作者：Takehiko Nishio、Norikazu Okuda、Choji Kashima

  DOI：10.1002/hlca.19900730616

  日期：1990.9.19

  Reduction of indolin-2-ones with lithium aluminium hydride (LAH) or diisobutylaluminum hydride (DIBAL) and desulfurization of indoline-2-thiones with Raney-Ni were investigated. Treatment of indoline-2-ones 1 with LAH or DIBAL yield indoles 4 and/or indolines 3 in moderate-to high yield depending on the substituents at N and C(3) of 1. Indoline-2-thiones 2 were desulfurized with Raney-Ni to give indoles

  研究了用氢化铝锂（LAH）或氢化二异丁基铝（DIBAL）还原吲哚-2-酮和用阮内镍（Raney -Ni ）对吲哚啉-2-硫酮进行脱硫。用LAH或DIBAL处理indoline-2-ones 1时，根据N和C（3）1处的取代基，可中等至高产率产生吲哚4和/或indolines 3。二氢吲哚-2-硫酮2与被脱硫阮内-Ni，得到吲哚4和/或二氢吲哚3。
• Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment of prevention of diseases characterized by abnormal cell proliferation
  申请人：Children's Medical Center Corporation

  公开号：US20020198188A1

  公开（公告）日：2002-12-26

  The present invention provides substituted 3,3-diphenyl indanone, indane and indole compounds, as well as analogues thereof, which are specific, potent and safe inhibitors of mammalian cell proliferation. The compounds can be used to inhibit mammalian cell proliferation in situ as a therapeutic approach towards the treatment or prevention of diseases characterized by abnormal cell proliferation, such as cancer.

  本发明提供了取代的3,3-二苯基茚酮，茚烷和吲哚化合物及其类似物，它们是哺乳动物细胞增殖的特异性，有效和安全的抑制剂。这些化合物可用于抑制哺乳动物细胞在体内的增殖，作为治疗或预防由于细胞异常增殖而表现为疾病的方法，例如癌症。
• Methods for the treatment or prevention of inflammatory diseases characterized by abnormal cell proliferation
  申请人：——

  公开号：US20020128256A1

  公开（公告）日：2002-09-12

  The present invention provides substituted 3,3-diphenyl indanone, indane and indole compounds, as well as analogues thereof which are specific, potent and safe inhibitors of the Ca 2+ -activated potassium channel (Gardos channel) of erythrocytes. The compounds can be used as efficacious drugs in the treatment of sickle cell disease and diseases characterized by unwanted or abnormal cell proliferation, and in particular inflammatory diseases associated with unwanted cellular proliferation.

  本发明提供了取代的3,3-二苯基茚酮、茚烷和吲哚化合物，以及特异性、有效和安全的类似物，它们是红细胞的Ca2+-活化钾通道（Gardos通道）的抑制剂。这些化合物可以作为治疗镰状细胞病和以不需要或异常细胞增殖为特征的疾病的有效药物，特别是与不需要的细胞增殖相关的炎症性疾病。
• Merging C–H Bond Activation, Alkyne Insertion, and Rearrangements by Rh(III)-Catalysis: Oxindole Synthesis from Nitroarenes and Alkynes
  作者：Marie Peng、Chang-Sheng Wang、Pan-Pan Chen、Thierry Roisnel、Henri Doucet、K. N. Houk、Jean-François Soulé

  DOI：10.1021/jacs.2c10932

  日期：2023.3.1

  Rh(III)-catalyzed ortho-C–H bond functionalization of nitroarenes with 1,2-diarylalkynes and carboxylic anhydrides. The reaction unpredictably affords 3,3-disubstituted oxindoles with the formal reduction of the nitro group under redox-neutral conditions. Besides good functional group tolerance, this transformation allows the preparation of oxindoles with a quaternary carbon stereocenter using nonsymmetrical 1,2-diarylalkynes

  我们报道了 Rh(III) 催化的硝基芳烃与 1,2-二芳基炔烃和羧酸酐的邻位 -C-H 键官能化。该反应出乎意料地提供了 3,3-二取代羟吲哚，在氧化还原中性条件下硝基被正式还原。除了良好的官能团耐受性外，这种转化还允许使用非对称 1,2-二芳基炔烃制备具有季碳立构中心的羟吲哚。通过使用功能化的环戊二烯基 (Cp TMP *)Rh(III) [Cp TMP* = 1-(3,4,5-trimethoxyphenyl)-2,3,4,5-tetramethylcyclopentadienyl] 我们开发的催化剂，它结合了椭圆形的富电子特性。机理研究，包括分离三种红花环中间体和广泛的密度泛函理论计算，表明反应通过 C-H 键活化级联反应通过亚硝基芳烃中间体进行─O-原子转移─[1,2]-芳基转移─脱氧─ N-酰化。
• Copper-Catalyzed Chemoselective O-Arylation of Oxindoles: Access to Cyclic Aryl Carboxyimidates
  作者：Prasoon Raj Singh、Manisha Lamba、Avijit Goswami

  DOI：10.1021/acs.joc.3c02341

  日期：2024.3.1

  chemoselective CuO-catalyzed strategy for the O-arylation of 2-oxindoles to synthesize 2-phenoxy-3H-indole and 2-phenoxy-1H-indole derivatives in the presence of diaryl iodonium salts. This method offers a variety of O-arylated oxindoles in good to excellent yields under relatively milder reaction conditions. Furthermore, this methodology was extended for the O-arylation of 2-pyridinone and isoindoline-1-one

  我们开发了一种高效的无碱和无添加剂的化学选择性 CuO 催化策略，用于在存在 2-oxindoles 的情况下进行 O-芳基化合成 2-phenoxy-3 H -indole 和 2-phenoxy-1 H -indole 衍生物。二芳基碘鎓盐。该方法在相对温和的反应条件下以良好至优异的收率提供了各种O-芳基化羟吲哚。此外，该方法还扩展到 2-吡啶酮和异吲哚啉-1-酮衍生物的 O-芳基化。