2-(9H-carbazol-9-yl)thiazole | 1313899-89-6

• 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: 2-(9H-carbazol-9-yl)thiazole
• 英文别名: 2-Carbazol-9-yl-1,3-thiazole
• CAS: 1313899-89-6
• 化学式: C₁₅H₁₀N₂S
• 分子量: 250.324
• InChiKey: CJVFGMQNXNLKQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(9H-carbazol-9-yl)thiazole 、 对碘苯甲酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 silver nitrate 作用下， 以 二甲基亚砜 为溶剂， 反应 7.0h， 以74%的产率得到2-(carbazol-9-yl)-5-(4-ethoxycarbonylphenyl)thiazole
  参考文献：
  名称：

  Copper-catalyzed oxidative C‒H, N‒H coupling of azoles and thiophenes

  摘要：

  C-H, N-H coupling of azole and thiophene derivatives takes place in the presence of a catalytic amount of Cu(OAc)(2) and an additive. The reaction of azoles smoothly occurs with several amines and amides catalyzed by 20 mol % of Cu(OAc)(2)-2PPh(3) and 4 equiv of NaOAc under O-2 or in the presence of Ag2CO3 under N-2. The coupling reaction leads to a facile synthesis of a N-substituted analogue of 2,5-diarylthiazole, which shows photoluminescent properties with extended pi-conjugation. Spectroscopic characteristics of the obtained thiazole derivatives are discussed by measurements of UV-vis absorption and photoluminescent spectra. Under the reaction conditions using Ag2CO3 as an additive and Cu(OAc)2-2PPh3 as a catalyst, thiophene derivatives also react with 2-pyrrolidone to undergo C-H, N-H amidation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.001
• 作为产物：
  描述：

  噻唑 、 咔唑 在 copper diacetate 、 三苯基膦 、 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以66%的产率得到2-(9H-carbazol-9-yl)thiazole
  参考文献：
  名称：

  Copper-catalyzed oxidative C‒H, N‒H coupling of azoles and thiophenes

  摘要：

  C-H, N-H coupling of azole and thiophene derivatives takes place in the presence of a catalytic amount of Cu(OAc)(2) and an additive. The reaction of azoles smoothly occurs with several amines and amides catalyzed by 20 mol % of Cu(OAc)(2)-2PPh(3) and 4 equiv of NaOAc under O-2 or in the presence of Ag2CO3 under N-2. The coupling reaction leads to a facile synthesis of a N-substituted analogue of 2,5-diarylthiazole, which shows photoluminescent properties with extended pi-conjugation. Spectroscopic characteristics of the obtained thiazole derivatives are discussed by measurements of UV-vis absorption and photoluminescent spectra. Under the reaction conditions using Ag2CO3 as an additive and Cu(OAc)2-2PPh3 as a catalyst, thiophene derivatives also react with 2-pyrrolidone to undergo C-H, N-H amidation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.001

文献信息

• Organometallic complex and light-emitting element containing the same
  申请人：Semiconductor Energy Laboratory Co., Ltd.

  公开号：US20040230061A1

  公开（公告）日：2004-11-18

  Organometallic complexes represented by chemical formula 1 are synthesized. In chemical formula 1, R 1 to R 5 , are individually a hydrogen atom, a halogen atom, a lower alkyl group, an alkoxy group, an acyl group, a nitro group, a cyano group, an amino group, a dialkylamino group, a diarylamino group, a vinyl group, an aryl group, or a heterocyclic group. Each pair of R 1 and R 2 , R 2 and R 3 , and R 4 and R 5 may be bonded each other to form aromatic rings. Y is a heterocyclic group containing nitrogen atoms as hetero atoms. M is atoms of group 9 in the periodic table or atoms of group 10 in the periodic table. When the M is atoms of group 9 in the periodic table, n=2. When the M is atoms of group 10 in the periodic table, n=1. L is a monoanionic bidentate chelate ligand having a beta diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, or a monoanionic bidentate chelate ligand having a phenol hydroxyl group. 1

  化学式1代表的有机金属配合物已合成。在化学式1中，R1至R5分别是氢原子、卤素原子、低碳基团、烷氧基团、酰基、硝基、氰基、氨基、二烷基氨基、二芳基氨基、乙烯基、芳基或杂环基中的一个。R1和R2、R2和R3、R4和R5中的每对可能相互键合形成芳香环。Y是含有氮原子作为杂原子的杂环基。M是周期表中9族元素或周期表中10族元素的原子。当M是周期表中9族元素的原子时，n=2。当M是周期表中10族元素的原子时，n=1。L是具有β-二酮结构的单阴离子双齿螯合配体、具有羧基的单阴离子双齿螯合配体，或具有酚羟基的单阴离子双齿螯合配体。
• Diversification of Carbazoles by LiCl-mediated Catalytic CuI Reaction
  作者：Joong-Hyun Cho、Young-Sil Ryu、Se-Hwan Oh、Jae-Kwan Kwon、Eul-Kgun Yum

  DOI：10.5012/bkcs.2011.32.7.2461

  日期：2011.7.20
• N-Arylation of carbazole by microwave-assisted ligand-free catalytic CuI reaction
  作者：Jae Kwan Kwon、Joong Hyun Cho、Young-Sil Ryu、Se Hwan Oh、Eul Kgun Yum

  DOI：10.1016/j.tet.2011.05.022

  日期：2011.7

  N-Arylation of carbazole has been achieved in high yields within 1 h using a microwave-assisted catalytic CuI reaction with no organic ligand. The N-arylation can be performed by various arylhalides, such as phenyl, pyridine, thiophene, and thiazole moieties. Specifically, N-arylated bromocarbazoles were converted into useful synthetic intermediates for functionalized carbazole materials. (C) 2011 Elsevier Ltd. All rights reserved.
• US6998492B2
  申请人：——

  公开号：US6998492B2

  公开（公告）日：2006-02-14
• US7314769B2
  申请人：——

  公开号：US7314769B2

  公开（公告）日：2008-01-01