5-(9H-carbazol-9-yl)-2-methylbenzo[d]thiazole | 556836-57-8

• 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: 5-(9H-carbazol-9-yl)-2-methylbenzo[d]thiazole
• 英文别名: 9-(2-Methyl-benzothiazol-5-yl)-9H-carbazole；5-carbazol-9-yl-2-methyl-1,3-benzothiazole
• CAS: 556836-57-8
• 化学式: C₂₀H₁₄N₂S
• 分子量: 314.411
• InChiKey: LYDOJHADDICAGN-UHFFFAOYSA-N

物化性质

• 沸点：
  450.1±27.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(9H-carbazol-9-yl)-2-methylbenzo[d]thiazole 在 喹啉 作用下， 以 甲苯 、 正丁醇 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Syntheses and spectroscopic properties of energy transfer systems based on squaraines

  摘要：

  The purpose of this project was to prepare fluorescent dyes that could absorb energy at relatively short wavelengths, and fluoresce in the near-IR region. To achieve this, copper- and palladium-mediated C-N couplings were used to prepare the 'cassettes', i.e the carbazole derivative 3b and the carbazole-, phenothiazine-, and phenoazine-squaraines 4b-d. These compounds have carbazole, phenothiazine, and phenoazine donor-components that absorb around about 300-320 nm, and squaraine acceptor-parts that fluoresce in the range 650-700 nm. The efficiencies of energy transfer from the donor to the acceptor, and the overall quantum yields of the cassettes were determined. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00383-1
• 作为产物：
  描述：

  5-溴-2-甲基苯并噻唑 、 咔唑 在 tris-(dibenzylideneacetone)dipalladium(0) 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以82%的产率得到5-(9H-carbazol-9-yl)-2-methylbenzo[d]thiazole
  参考文献：
  名称：

  Syntheses and spectroscopic properties of energy transfer systems based on squaraines

  摘要：

  The purpose of this project was to prepare fluorescent dyes that could absorb energy at relatively short wavelengths, and fluoresce in the near-IR region. To achieve this, copper- and palladium-mediated C-N couplings were used to prepare the 'cassettes', i.e the carbazole derivative 3b and the carbazole-, phenothiazine-, and phenoazine-squaraines 4b-d. These compounds have carbazole, phenothiazine, and phenoazine donor-components that absorb around about 300-320 nm, and squaraine acceptor-parts that fluoresce in the range 650-700 nm. The efficiencies of energy transfer from the donor to the acceptor, and the overall quantum yields of the cassettes were determined. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00383-1

文献信息

• Trivalent Organostibines: Sb,N Ligands in Double N-Arylation of Primary Amines toward Functionalized Carbazoles
  作者：Lifen Peng、Yanting Zhao、Jiayi Chen、Hao Lu、Zilong Tang、Yi Chen、Shuang-Feng Yin、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.joc.3c01863

  日期：2024.1.5

  A Sb,N ligand (L-Sb) for Pd-catalyzed double N-arylation of primary amines was developed. This trivalent ligand L-Sb, containing a 5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine skeleton and stable under air and moisture, could be synthesized facilely on a gram scale from chlorostibine (1) and cyclopentylmagnesium bromide. L-Sb showed excellent catalytic performance in Pd2(dba)3-catalyzed double

  开发了一种用于 Pd 催化伯胺双 N-芳基化的 Sb,N 配体 ( L-Sb )。这种三价配体L-Sb含有 5,6,7,12-四氢二苯并[ c , f ][1,5]氮杂替博辛骨架，在空气和湿气下稳定，可以从氯锑碱轻松合成克级 ( 1 )和环戊基溴化镁。 L-Sb在 Pd 2 (dba) 3催化的 2,2'-二溴-1,1'-联苯 ( 2 ) 与伯胺 ( 3 ) 的双 N-芳基化反应中表现出优异的催化性能，以良好的产率提供官能化咔唑。该Pd 2 (dba) 3 / L-Sb催化的双N-芳基化反应是三价有机锑化合物作为配体应用于N-芳基化反应的首例，具有催化剂负载量小、官能团耐受性广、化学稳定性好等优点。产率以及克级合成的简易性。