2-phenyl-3-(1-phenylvinyl)-1H-indole | 1088487-51-7

• 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: 2-phenyl-3-(1-phenylvinyl)-1H-indole
• 英文别名: 2-phenyl-3-(1-phenylethenyl)-1H-indole
• CAS: 1088487-51-7
• 化学式: C₂₂H₁₇N
• 分子量: 295.384
• InChiKey: ILUDOURVNVBMAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.79
• 氢给体数：
  1.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2-phenyl-3-(1-phenylvinyl)-1H-indole 在 一溴化碘 作用下， 以 氯苯 为溶剂， 以57%的产率得到6-phenyl-11H-benzo[a]carbazole
  参考文献：
  名称：

  Metal-Free Double Csp²–H Bond Functionalization: Strategy for Synthesizing Benzo[a]carbazoles from 2-Arylindoles and Acetophenones/Alkynes

  摘要：

  A metal-free strategy for the synthesis of benzocarbazoles from 2-arylindoles and aryl ketones is developed. Various 2-aryl-3-vinyl-indoles were generated in situ through dehydrative condensation of aryl ketones and indoles. These key intermediates could be selectively converted into the corresponding benzo[a]carbazoles via a direct cyclization process between two Csp(2)-H bonds. Furthermore, terminal alkynes also could be used as the versatile C2 source to afford the corresponding products in good yields.

  DOI：

  10.1021/acs.orglett.9b01138
• 作为产物：
  描述：

  苯肼 在 一溴化碘 作用下， 以 氯苯 为溶剂， 反应 8.0h， 生成 2-phenyl-3-(1-phenylvinyl)-1H-indole
  参考文献：
  名称：

  Metal-Free Double Csp²–H Bond Functionalization: Strategy for Synthesizing Benzo[a]carbazoles from 2-Arylindoles and Acetophenones/Alkynes

  摘要：

  A metal-free strategy for the synthesis of benzocarbazoles from 2-arylindoles and aryl ketones is developed. Various 2-aryl-3-vinyl-indoles were generated in situ through dehydrative condensation of aryl ketones and indoles. These key intermediates could be selectively converted into the corresponding benzo[a]carbazoles via a direct cyclization process between two Csp(2)-H bonds. Furthermore, terminal alkynes also could be used as the versatile C2 source to afford the corresponding products in good yields.

  DOI：

  10.1021/acs.orglett.9b01138

文献信息

• Indium(III) Catalyzed Reactions of Vinyl Azides and Indoles
  作者：Atul A. More、Alex M. Szpilman

  DOI：10.1021/acs.orglett.0c00919

  日期：2020.5.15

  Indium trichloride catalyzes the reaction of vinyl azides with unfunctionalized indoles to give vinyl indoles. This is the first example of displacement of the azide group by a carbon nucleophile while preserving the vinyl function. The protocol employs very mild reaction conditions and offers excellent yields of diverse 3-vinyl indoles. It is amenable to gram scale. Access to a library of 3,3'-bis(indolyl)methanes

  三氯化铟催化叠氮化乙烯与未官能化的吲哚的反应，生成乙烯基吲哚。这是在保持乙烯基官能的同时，碳亲核试剂取代叠氮化物基团的第一个例子。该方案采用非常温和的反应条件，并提供了各种3-乙烯基吲哚的优异收率。它适合克规模。展示了通过叠氮化乙烯基酯与2当量吲哚的缩合获得3,3'-双（吲哚基）甲烷的文库。
• Indium-Catalyzed Annulation of 2-Aryl- and 2-Heteroarylindoles with Propargyl Ethers: Concise Synthesis and Photophysical Properties of Diverse Aryl- and Heteroaryl-Annulated[<i>a</i>]carbazoles
  作者：Teruhisa Tsuchimoto、Hiromichi Matsubayashi、Masayoshi Kaneko、Yuta Nagase、Takuhiro Miyamura、Eiji Shirakawa

  DOI：10.1021/ja803954e

  日期：2008.11.26

  is applicable also to symmetrical dimers such as bithiophene and bifuran derivatives. Mechanistic studies suggest that the first step is addition reaction initiated by regioselective nucleophilic attack of the C3 of 2-aryl- and 2-heteroarylindoles to the internal carbon atom of the C[triple bond]C bond in propargyl ethers. The next stage is ring-closing S(N)2 process kicking out the alkoxy group and

  在催化量的九氟丁烷磺酸铟 [In(ONf)(3)] 存在下，用炔丙基醚处理 2-芳基-和 2-杂芳基吲哚，以良好的产率得到芳基-和杂芳基-环化的 [a] 咔唑。合成上有吸引力的特征反映在其对广泛范围的 2-芳基-和 2-杂芳基吲哚的适用性上。在环化反应中，炔丙醚作为 C3 源（HC[三键]C-CH(2)OR）。其中，两个碳原子作为新构建的芳环的成员并入产物中，剩余的碳原子在芳环上形成甲基，其中甲基始终位于吲哚核的 C3 位置旁边。甲基可以通过 SeO(2) 氧化轻松去除，然后用 RhCl(CO)(PPh(3))(2)-Ph(2)P(CH(2))(3)PPh(2) 脱羰，如一种催化剂。新的环化策略也适用于对称二聚体，如联噻吩和双呋喃衍生物。机理研究表明，第一步是通过 2-芳基-和 2-杂芳基吲哚的 C3 与炔丙醚中 C[三键]C 键的内部碳原子的区域选择性亲核攻击引发的加成反应。下一阶段是闭环
• Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes
  作者：Euan B. McLean、Francesca M. Cutolo、Orla J. Cassidy、David J. Burns、Ai-Lan Lee

  DOI：10.1021/acs.orglett.0c02526

  日期：2020.9.4

  Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-catalyzed reaction can be fully switched to allow for isolation of the vinylindole products instead. Furthermore, this selective reaction can be utilized to synthesize the more difficult to access unsymmetrical BIMs from readily available starting materials.