1,3-dichloro-9H-carbazole | 56234-47-0

• 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: 1,3-dichloro-9H-carbazole
• 英文别名: 1,3-dichlorocarbazole；9H-Carbazole, 1,3-dichloro-
• CAS: 56234-47-0
• 化学式: C₁₂H₇Cl₂N
• 分子量: 236.1
• InChiKey: WDRFQIRRQYFHOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,4-二氯-6-碘苯胺 在 palladium diacetate cesium fluoride 、 三环己基膦 作用下， 以 乙腈 为溶剂， 反应 34.0h， 生成 1,3-dichloro-9H-carbazole
  参考文献：
  名称：

  Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization

  摘要：

  An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.071

文献信息

• Amino-Directed Rh^III-Catalyzed CH Activation Leading to One-Pot Synthesis of NH Carbazoles
  作者：Qibai Jiang、Dandan Duan-Mu、Wei Zhong、Hao Chen、Hong Yan

  DOI：10.1002/chem.201203856

  日期：2013.2.4

  One‐pot synthesis: An efficient amino‐directed one‐pot synthesis of NH carbazoles from unprotected 2‐aminobiaryl compounds is reported. The free amino unit acts as both a directing group for ortho CH activation and a functional group for construction of an N‐heterocyclic ring (see scheme).

  一锅合成：N的一个高效氨基定向的一锅合成从未保护的2- aminobiaryl化合物ħ咔唑报道。游离氨基单元充当两者引导组邻Ç  ħ活化和用于建筑的N-杂环的官能团（参见方案）。
• Synthesis of Carbazoles and Dibenzofurans via Cross-Coupling of <i>o</i>-Iodoanilines and <i>o</i>-Iodophenols with Silylaryl Triflates
  作者：Zhijian Liu、Richard C. Larock

  DOI：10.1021/ol048564l

  日期：2004.10.1

  An efficient route to synthesize a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. This chemistry tolerates a variety of functional groups.
• Direct Synthesis of <i>N</i>-H Carbazoles via Iridium(III)-Catalyzed Intramolecular C–H Amination
  作者：Chiharu Suzuki、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/acs.orglett.5b00502

  日期：2015.3.20

  The iridium-catalyzed dehydrogenative cyclization of 2-aminobiphenyls proceeds smoothly in the presence of a copper cocatalyst under air as a terminal oxidant through intramolecular direct C-H amination to produce N-H carbazoles. A similar iridium/copper system can also catalyze the unprecedented dimerization reaction of 2-aminobiphenyl involving 2-fold C-H/N-H couplings.
• Rh(I)-catalyzed decarbonylation synthesis of carbazoles via C–N cleavage
  作者：Weizheng Fan、Shan Jiang、Bainian Feng

  DOI：10.1016/j.tet.2015.04.058

  日期：2015.6

  A one-pot Rh(I)-catalyzed synthesis of 9-H carbazoles via C-N bond cleavage by activation of aldehyde C-H bonds is reported. This protocol offers good yields and tolerates a broad range of functional groups. Based on the extensive control experiments, we propose a plausible decarbonylation mechanism. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization
  作者：Zhijian Liu、Richard C. Larock

  DOI：10.1016/j.tet.2006.10.071

  日期：2007.1

  An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps. (c) 2006 Elsevier Ltd. All rights reserved.