(3-fluorophenyl)(1H-indol-3-yl)methanone | 1086398-73-3

• 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-fluorophenyl)(1H-indol-3-yl)methanone
• 英文别名: (3-fluorophenyl)-(1H-indol-3-yl)methanone
• CAS: 1086398-73-3
• 化学式: C₁₅H₁₀FNO
• mdl: MFCD11501331
• 分子量: 239.249
• InChiKey: LXOBDWOHMQPMBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-fluorophenyl)(1H-indol-3-yl)methanone 、 5-甲基吲哚 在 C₇₆H₅₇F₁₂NO₆P₂ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.17h， 以99%的产率得到(R)-3-(1-(3-fluorophenyl)-1-(1H-indol-3-yl)ethyl)-5-methyl-1H-indole
  参考文献：
  名称：

  手性亚氨基二磷酸催化吡咯和吲哚向3-Vinylindoles的亲核加成反应，不对称合成1,1,1-三芳基乙烷。

  摘要：

  手性亚氨基二磷酸在吡咯和吲哚对3-乙烯基吲哚的对映选择性加成反应中用作有效的催化剂。以优异的产率（高达99％的产率）和对映选择性（高达ee的98％）合成了一系列带有四级立体中心的旋光1,1,1-三芳基乙氧基。1i和2a以及1o和5a的克级反应证明了该方法的综合实用性。对照实验表明，为获得优异的结果，必须在催化剂和底物之间形成双氢键。

  DOI：

  10.1021/acs.joc.9b02024
• 作为产物：
  描述：

  吲哚 、 N-(3-氟苄基)苯胺 在 叔丁基过氧化氢 、 三甲基丙酮酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 iron(II) chloride 作用下， 以 癸烷 、 二甲基亚砜 为溶剂， 反应 24.0h， 以85%的产率得到(3-fluorophenyl)(1H-indol-3-yl)methanone
  参考文献：
  名称：

  Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N–H) Indoles Using Anilines as the Carbonyl Source

  摘要：

  C3-selective formylation and acylation of free (N-H) indoles under mild conditions can be achieved by using Ru- and Fe-catalyzed oxidative coupling of free (N-H) indoles with anilines, respectively. Both processes are operationally simple, compatible with a variety of functional groups and generally provide the desired products in good yields. (13)C-labeling experiments unambiguously established that the carbonylic carbon in the formylation products originated from methyl group of N-methyl aniline.

  DOI：

  10.1021/ja2048495

文献信息

• Synthesis of 3-Aroylindoles as Intermediates of Cannabimimetics and Elucidation of Their Physicochemical Properties
  作者：Hideyo Takahashi、Koji Araki、Kosho Makino、Hidetsugu Tabata、Hiroshi Nakayama、Kei Zaitsu、Tetsuta Oshitari、Hideaki Natsugari

  DOI：10.3987/com-18-13888

  日期：——

  In order to synthesize the intermediates of cannabimimetics, the benzoylation of indoles with 2'/3'/4'-substituted benzoyl chloride in the presence of Et2AlCl was examined. Among the products, we found that the H-1 NMR spectra of 3-(2'-substituted)-benzoyl-2-methylindoles had interesting features. We investigated their physicochemical properties based on VT-NMR, and it was revealed that conformer A (s-trans) is present in preference to conformer B in these compounds.
• Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N–H) Indoles Using Anilines as the Carbonyl Source
  作者：Wenliang Wu、Weiping Su

  DOI：10.1021/ja2048495

  日期：2011.8.10

  C3-selective formylation and acylation of free (N-H) indoles under mild conditions can be achieved by using Ru- and Fe-catalyzed oxidative coupling of free (N-H) indoles with anilines, respectively. Both processes are operationally simple, compatible with a variety of functional groups and generally provide the desired products in good yields. (13)C-labeling experiments unambiguously established that the carbonylic carbon in the formylation products originated from methyl group of N-methyl aniline.
• Asymmetric Synthesis of 1,1,1-Triarylethanes by Chiral Imidodiphosphoric Acid Catalyzed Nucleophilic Addition of Pyrrole and Indoles to 3-Vinylindoles
  作者：Xu-Kai Guan、Heng Zhang、Ji-Gang Gao、Dong-Yang Sun、Xiang-Shuo Qin、Guo-Feng Jiang、Guang-Liang Zhang、Suoqin Zhang

  DOI：10.1021/acs.joc.9b02024

  日期：2019.10.4

  Chiral imidodiphosphoric acids were employed as efficient catalysts in the enantioselective addition reaction of pyrrole and indoles to 3-vinylindoles. A series of optically active 1,1,1-triarylethmanes bearing quaternary stereocenters were synthesized in excellent yields (up to 99% yield) and enantioselectivities (up to 98% ee). Gram-scale reactions of 1i and 2a as well as 1o and 5a demonstrated the

  手性亚氨基二磷酸在吡咯和吲哚对3-乙烯基吲哚的对映选择性加成反应中用作有效的催化剂。以优异的产率（高达99％的产率）和对映选择性（高达ee的98％）合成了一系列带有四级立体中心的旋光1,1,1-三芳基乙氧基。1i和2a以及1o和5a的克级反应证明了该方法的综合实用性。对照实验表明，为获得优异的结果，必须在催化剂和底物之间形成双氢键。