9-(pyrimidin-2-yl)-9H-carbazole-1-carbonitrile | 1581695-39-7

• 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: 9-(pyrimidin-2-yl)-9H-carbazole-1-carbonitrile
• 英文别名: 9-Pyrimidin-2-ylcarbazole-1-carbonitrile
• CAS: 1581695-39-7
• 化学式: C₁₇H₁₀N₄
• 分子量: 270.293
• InChiKey: XNIXPAWCPUPOGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  异氰酸叔丁酯 、 9-(pyrimidin-2-yl)-9H-carbazole 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) trifluoroacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以55%的产率得到9-(pyrimidin-2-yl)-9H-carbazole-1-carbonitrile
  参考文献：
  名称：

  Rhodium-Catalyzed Direct C–H Bond Cyanation of Arenes with Isocyanide

  摘要：

  An efficient rhodium-catalyzed regioselective C-H bond cyanation of arenes was developed using tert-butyl isocyanide as the cyanide source. A wide range of (hetero)aryl and cycloalkenyl nitriles could be afforded with high regioselectivity and good functional group tolerance.

  DOI：

  10.1021/jo500087g

文献信息

• Rhodium(III)-Catalyzed Selective CH Cyanation of Indolines and Indoles with an Easily Accessible Cyano Source
  作者：Neeraj Kumar Mishra、Taejoo Jeong、Satyasheel Sharma、Youngmi Shin、Sangil Han、Jihye Park、Joa Sub Oh、Jong Hwan Kwak、Young Hoon Jung、In Su Kim

  DOI：10.1002/adsc.201401152

  日期：2015.4.13

  The rhodium‐catalyzed selective cyanation of CH bonds of indolines and indoles with N‐cyano‐N‐phenyl‐para‐methylbenzenesulfonamide is described. This protocol offers a facile access to C‐7 cyanated indolines and C‐2 cyanated indoles with high site selectivity and excellent functional group tolerance.

  本文描述了铑催化的N-氰基-N-苯基-对-甲基苯磺酰胺对二氢吲哚和吲哚CH键的选择性氰化反应。该协议可轻松实现C-7氰基吲哚和C-2氰基吲哚的高位点选择性和出色的官能团耐受性。
• Copper-Mediated Direct Cyanation of Heteroarene and Arene C–H Bonds by the Combination of Ammonium and DMF
  作者：Shengbo Xu、Jiangang Teng、Jin-Tao Yu、Song Sun、Jiang Cheng

  DOI：10.1021/acs.orglett.9b03861

  日期：2019.12.20

  A copper-mediated cyanation of heteroarene and arene C-H bonds has been developed, where ammonium iodide and DMF served as a safe cyanating combination. This procedure shows a broad substrate scope, allowing the facile access of 2-cyano indole, 1-cyano carbazole, 2-cyano pyrrole, and 2-cyano 1-pyridinyl benzene in high yields with good functional group tolerance.

  已经开发出铜介导的杂芳烃和芳烃CH键的氰化，其中碘化铵和DMF用作安全的氰化组合。该方法显示了广泛的底物范围，允许以高收率和良好的官能团耐受性容易地获得2-氰基吲哚，1-氰基咔唑，2-氰基吡咯和2-氰基1-吡啶基苯。
• Copper-Mediated Direct Aromatic ortho-C–H Cyanation by AIBN
  作者：Peng-Cheng Qian、Jiang Cheng、Aijun Zhou、Zhenlian Wang、Fan Chen

  DOI：10.1055/s-0037-1610795

  日期：2022.6

  We have developed a copper-mediated chelation-assisted direct aromatic ortho-C–H cyanation that uses AIBN as a safe cyanation reagent. The substrate scope included indoles, pyrroles, a carbazole, and a thiophene.

  我们开发了一种铜介导的螯合辅助直接芳族邻-C-H 氰化，它使用 AIBN 作为安全的氰化试剂。底物范围包括吲哚、吡咯、咔唑和噻吩。