3-chloro-11-methyl-5,6-diphenyl-11H-benzo[a]carbazole | 1401560-34-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 3-chloro-11-methyl-5,6-diphenyl-11H-benzo[a]carbazole
• 英文别名: 3-Chloro-11-methyl-5,6-diphenylbenzo[a]carbazole；3-chloro-11-methyl-5,6-diphenylbenzo[a]carbazole
• CAS: 1401560-34-6
• 化学式: C₂₉H₂₀ClN
• 分子量: 417.938
• InChiKey: DLENAPPBCYJSNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-((4-chlorophenyl)ethynyl)-N,N-dimethylaniline 、 二苯基乙炔 在 四丁基溴化铵 、 氧气 、 copper diacetate 、 sodium acetate 、 palladium diacetate 、 三甲基丙酮酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以72%的产率得到3-chloro-11-methyl-5,6-diphenyl-11H-benzo[a]carbazole
  参考文献：
  名称：

  Palladium(II)-Catalyzed Tandem Cyclization/C–H Functionalization of Alkynes for the Synthesis of Functionalized Indoles

  摘要：

  A palladium-catalyzed tandem cyclization/C-H functionalization of two alkynes was accomplished to construct a series of polycyclic functionalized indoles. A range of internal alkynes bearing synthetically useful functional groups were tolerated. A good regioselectivity was observed when alkyl-substituted alkynes were introduced into the reaction system, and a single product was obtained. Molecular oxygen was used as the terminal oxidant in the approach, rendering the reaction more sustainable.

  DOI：

  10.1021/jo301741j

文献信息

• Double C-H Functionalization to Construct Polycyclic Heteroarenes Catalyzed by an Ionic Salt of a Pd Complex with an N-Heterocyclic Carbene Ligand
  作者：Sanjay Kumar Ghosh、Bing-Chiuan Kuo、Hsiang-Yu Chen、Jia-Ying Li、Shuang-De Liu、Hon Man Lee

  DOI：10.1002/ejoc.201500417

  日期：2015.7

  A new ionic salt, cis-[Pd(L)(PPh3)(H2O)2](SO3CF3)2 (A), in which L is an amido-functionalized N-heterocyclic carbene (NHC) ligand, has been prepared by the salt metathesis reaction between [Pd(L)(PPh3)Cl2] and AgOTf in wet acetonitrile. It was successfully characterized by NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. Complex A was found to be effective in catalyzing

  一种新的离子盐，顺式-[Pd(L)(PPh3)(H2O)2](SO3CF3)2 (A)，其中 L 是酰胺基官能化的 N-杂环卡宾 (NHC) 配体，由[Pd(L)(PPh3)Cl2] 和 AgOTf 在湿乙腈中的盐复分解反应。通过核磁共振谱、元素分析和单晶X射线衍射分析成功地对其进行了表征。发现配合物 A 在 Cu(OAc)2 和四正丁基溴化铵的存在下，可有效催化各种含氮和硫杂芳烃的双 C-H 官能化，以与炔烃形成稠合的多环杂芳烃化合物。吲哚、噻吩、咪唑并[1,2-a] 吡啶和咪唑用作底物。特别是，在所采用的条件下，可以获得有趣的咪唑并[5,1,2-cd]吲哚嗪化合物。
• 10.1021/acs.joc.4c00746
  作者：Zhang, Lijun、Wang, Zhuo、Song, Zhiguang

  DOI：10.1021/acs.joc.4c00746

  日期：——

  benzo[a]carbazole and dibenzo[c,g]carbazole frameworks. The detailed gold catalytic reaction conditions developed for the challenging intermolecular carbon nucleophilic addition to internal alkynes are realized, giving the desired alkyne hydroarylation products in good yields. The resulting trisubstituted alkenes are able to undergo photomediated cyclization, furnishing the desired carbazole molecules

  在此，我们报告了构建苯并[ a ]咔唑和二苯并[ c ， g ]咔唑框架的反应方案。实现了为内部炔烃进行具有挑战性的分子间碳亲核加成而开发的详细金催化反应条件，以良好的收率得到了所需的炔烃加氢芳基化产物。所得三取代烯烃能够进行光介导环化，以优异的产率和高效率提供所需的咔唑分子。
• Palladium(II)-Catalyzed Tandem Cyclization/C–H Functionalization of Alkynes for the Synthesis of Functionalized Indoles
  作者：Xiao-Feng Xia、Ning Wang、Lu−Lu Zhang、Xian-Rong Song、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/jo301741j

  日期：2012.10.19

  A palladium-catalyzed tandem cyclization/C-H functionalization of two alkynes was accomplished to construct a series of polycyclic functionalized indoles. A range of internal alkynes bearing synthetically useful functional groups were tolerated. A good regioselectivity was observed when alkyl-substituted alkynes were introduced into the reaction system, and a single product was obtained. Molecular oxygen was used as the terminal oxidant in the approach, rendering the reaction more sustainable.