1-(9H-carbazol-3-yl)-3-phenylthiourea | 655229-65-5

• 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-(9H-carbazol-3-yl)-3-phenylthiourea
• CAS: 655229-65-5
• 化学式: C₁₉H₁₅N₃S
• 分子量: 317.414
• InChiKey: HZBDGFZGZLNLEF-UHFFFAOYSA-N

物化性质

• 熔点：
  196-197 °C
• 沸点：
  538.5±42.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.9
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(9H-carbazol-3-yl)-3-phenylthiourea 在 Montmorillonite K₁₀ clay 、 对甲苯磺酸 作用下， 反应 7.0h， 以73%的产率得到N-phenyl-6H-[1,3]thiazolo[4,5-c]carbazol-2-amine
  参考文献：
  名称：

  A clay-mediated, regioselective synthesis of 2-(aryl/alkyl)amino-thiazolo[4,5-c]carbazoles

  摘要：

  The 3-aminocarbazoles la-e were condensed with phenyl and benzyl isothiocyanates on montmorillonite K10 clay or TLC-grade silica gel at room temperature to furnish efficiently the N-phenyl and N-benzylthioureidocarbazoles, 2a-e and 2f, respectively. within minutes. When adsorbed on montmorillonite K 10 clay impregnated with para-toluene sulfonic acid (1:1, w/w) and heated at 60-70degreesC. 2a-e and 2f furnished the 2-anilino and 2-benzylaminothiazolo[4,5-c]carbazoles, 3a-e and 3f, respectively, regioselectively in high yields. The cyclisation was also effective for the N-methylthioureidocarbazoles 2g-i. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.129
• 作为产物：
  描述：

  3-氨基咔唑 、 硫代异氰酸苯酯 以 甲醇 为溶剂， 反应 1.0h， 以86%的产率得到1-(9H-carbazol-3-yl)-3-phenylthiourea
  参考文献：
  名称：

  噻唑并[4,5-c]-和-[5,4-b]-咔唑的新型便捷合成

  摘要：

  噻唑并[4,5-c]-和-[5,4-b]咔唑(6a-e, 7a, 8b-e)的新合成方法是由3-氨基咔唑(3a-e)分别与甲基缩合完成的和异硫氰酸苯酯，然后氧化环化生成的硫脲基咔唑（4a-e，5a）。

  DOI：

  10.3987/com-03-s(p)3

文献信息

• A Novel, Expedient Synthesis of Thiazolo[4,5-c]- and -[5,4-b]-carbazoles
  作者：Manas Chakrabarty、Nandita Ghosh、Yoshihiro Harigaya

  DOI：10.3987/com-03-s(p)3

  日期：——

  A new synthesis of thiazolo[4,5-c]- and -[5,4-b]carbazoles (6a-e, 7a, 8b-e) was accomplished from 3-aminocarbazoles (3a-e) by separate condensations with methyl and phenyl isothiocyanates, followed by oxidative cyclization of the resulting thioureidocarbazoles (4a-e, 5a).

  噻唑并[4,5-c]-和-[5,4-b]咔唑(6a-e, 7a, 8b-e)的新合成方法是由3-氨基咔唑(3a-e)分别与甲基缩合完成的和异硫氰酸苯酯，然后氧化环化生成的硫脲基咔唑（4a-e，5a）。
• A clay-mediated, regioselective synthesis of 2-(aryl/alkyl)amino-thiazolo[4,5-c]carbazoles
  作者：Manas Chakrabarty、Nandita Ghosh、Yoshihiro Harigaya

  DOI：10.1016/j.tetlet.2004.04.129

  日期：2004.6

  The 3-aminocarbazoles la-e were condensed with phenyl and benzyl isothiocyanates on montmorillonite K10 clay or TLC-grade silica gel at room temperature to furnish efficiently the N-phenyl and N-benzylthioureidocarbazoles, 2a-e and 2f, respectively. within minutes. When adsorbed on montmorillonite K 10 clay impregnated with para-toluene sulfonic acid (1:1, w/w) and heated at 60-70degreesC. 2a-e and 2f furnished the 2-anilino and 2-benzylaminothiazolo[4,5-c]carbazoles, 3a-e and 3f, respectively, regioselectively in high yields. The cyclisation was also effective for the N-methylthioureidocarbazoles 2g-i. (C) 2004 Elsevier Ltd. All rights reserved.