3,11-dimethyl-5,6-diphenyl-11H-benzo[a]carbazole | 1198116-17-4

• 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: 3,11-dimethyl-5,6-diphenyl-11H-benzo[a]carbazole
• 英文别名: 3,11-Dimethyl-5,6-diphenylbenzo[a]carbazole
• CAS: 1198116-17-4
• 化学式: C₃₀H₂₃N
• 分子量: 397.519
• InChiKey: NBKAMAANQSETCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  N,N-dimethyl-2-(p-tolylethynyl)aniline 、 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66%的产率得到3,11-dimethyl-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

• A Palladium-Catalyzed Oxidative Cycloaromatization of Biaryls with Alkynes Using Molecular Oxygen as the Oxidant
  作者：Zhuangzhi Shi、Shengtao Ding、Yuxin Cui、Ning Jiao

  DOI：10.1002/anie.200903975

  日期：2009.10.5

  Dual activation of CH bonds has enabled the preparation of polycyclic aromatics from arylindoles and arylbenzofurans in the absence of a directing group, and with using O2 as the oxidant (see scheme). Synthetically and medicinally important polycyclic aromatics have been easily prepared, and some of the resulting polycyclic heteroaromatics exhibit intense fluorescence.

  的Ç双重激活 H键，使从在不存在定向基团的arylindoles和arylbenzofurans多环芳烃的制备，以及使用ö 2作为氧化剂（参见方案）。合成上和医学上重要的多环芳族化合物很容易制备，并且某些所得的多环杂芳族化合物显示出强烈的荧光。
• Synthesis of Benzo[a]carbazoles and Dibenzo[c,g]carbazoles via Sequential Gold Catalysis and Photomediated Cyclization
  作者：Lijun Zhang、Zhuo Wang、Zhiguang Song

  DOI：10.1021/acs.joc.4c00746

  日期：2024.6.21

  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。