N, N-diphenylbenzo[d]thiazol-2-amine | 135085-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N, N-diphenylbenzo[d]thiazol-2-amine
• 英文别名: N,N-diphenyl-1,3-benzothiazol-2-amine
• CAS: 135085-79-9
• 化学式: C₁₉H₁₄N₂S
• 分子量: 302.4
• InChiKey: BHPSUURZXRQTIG-UHFFFAOYSA-N

物化性质

• 沸点：
  457.9±28.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N'-(2-chlorophenyl)-N,N-diphenylthiourea 以 甲醇 为溶剂， 反应 21.0h， 以49%的产率得到N, N-diphenylbenzo[d]thiazol-2-amine
  参考文献：
  名称：

  Muthusamy, Sengoden; Paramasivam, Rangasamy; Ramakrishnan, Vayalakkavoor T., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 3, p. 759 - 763

  摘要：

  DOI：

文献信息

• C–H Functionalization of Benzothiazoles via Thiazol-2-yl-phosphonium Intermediates
  作者：You Zi、Fritz Schömberg、Konrad Wagner、Ivan Vilotijevic

  DOI：10.1021/acs.orglett.0c00882

  日期：2020.5.1

  to form thiazol-2-yl-triphenylphosphonium salts, and these phosphonium salts react with a wide range of O- and N-centered nucleophiles to give the corresponding ethers, amines, and C-N biaryls. The reactions proceed under mild conditions and allow for the recovery of triphenylphosphine at the end of the sequence. In the presence of hydroxide, phosphonium salts undergo disproportionation, resulting in

  苯并噻唑与三苯基膦进行区域选择性 C2-H 官能化形成噻唑-2-基-三苯基鏻盐，这些鏻盐与多种 O 和 N 中心亲核试剂反应生成相应的醚、胺和 CN 联芳基。反应在温和条件下进行，并允许在序列末端回收三苯膦。在氢氧化物存在下，鏻盐发生歧化反应，导致苯并噻唑还原，这可用于苯并噻唑的特定 C2 氘化。
• One-Pot Synthesis of <i>N,N</i>-Diphenyl-2-benzothiazolamines from 1-(2-Iodophenyl)-3-phenylthioureas and Iodobenzenes
  作者：Jie Ma、Rong Feng、Hao-Lin Zhou、Er-Jun Hao、Zhen Shi、Zhi-Bing Dong

  DOI：10.1021/acs.joc.2c01789

  日期：2022.11.4

  An efficient copper-catalyzed synthesis of a variety of N,N-diphenyl-2-benzothiazolamines was developed. Starting from substituted 1-(2-iodophenyl)-3-phenylthioureas and substituted iodobenzenes, the reaction proceeded smoothly via a tandem manner in the presence of CuI to afford the corresponding N,N-diphenyl-2-benzothiazolamine derivatives with good functional group tolerance. The protocol features

  开发了一种有效的铜催化合成多种N,N-二苯基-2-苯并噻唑胺的方法。以取代的1-(2-碘苯基)-3-苯基硫脲和取代的碘苯为原料，在CuI存在下以串联方式顺利进行反应，得到相应的具有良好官能团耐受性的N,N-二苯基-2-苯并噻唑胺衍生物. 该协议具有性能简单、起始材料容易获得、一锅法和良好的官能团耐受性等特点，为多官能胺的制备提供了实用的策略。
• Direct Amination of Azoles via Catalytic C−H, N−H Coupling
  作者：Daiki Monguchi、Taiki Fujiwara、Hirotoshi Furukawa、Atsunori Mori

  DOI：10.1021/ol900298e

  日期：2009.4.2

  C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(OAc)(2) in xylene under an oxygen atmosphere afforded the aminated product in 81% yield.
• Copper-catalyzed oxidative C‒H, N‒H coupling of azoles and thiophenes
  作者：Shinobu Mitsuda、Taiki Fujiwara、Katsuyoshi Kimigafukuro、Daiki Monguchi、Atsunori Mori

  DOI：10.1016/j.tet.2012.03.001

  日期：2012.5

  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.
• FLUORANTHENE DERIVATIVE, LUMINESCENT ELEMENT MATERIAL CONTAINING SAME, AND LUMINESCENT ELEMENT
  申请人：Toray Industries, Inc.

  公开号：EP2907803B1

  公开（公告）日：2021-08-18