tert-butyl 2-chloro-10H-phenothiazine-10-carboxylate | 1401710-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: tert-butyl 2-chloro-10H-phenothiazine-10-carboxylate
• CAS: 1401710-40-4
• 化学式: C₁₇H₁₆ClNO₂S
• 分子量: 333.839
• InChiKey: BLAUNRVNJBYPDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  457.8±44.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-chloro-10H-phenothiazine-10-carboxylate 在 palladium diacetate 、 三氟乙酸 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 2-(4-methylpiperazin-1-yl)-10H-phenothiazine
  参考文献：
  名称：

  A new synthetic approach to phenothiazine-2-amines

  摘要：

  Elaboration of a Buchwald-Hartwig protocol for the introduction of amino functions to position 2 of the phenothiazine ring system has opened a new access to various N-alkyl and N-dienyl phenothiazines bearing secondary amines, tertiary amines, and amide moieties. Hydrolysis of the amido derivatives gave unsubstituted phenothiazine-2-amines. This protocol provides an easy access to phenothiazine-2-amines starting from the commercially available starting compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.083
• 作为产物：
  描述：

  2-氯吩噻嗪 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以84%的产率得到tert-butyl 2-chloro-10H-phenothiazine-10-carboxylate
  参考文献：
  名称：

  A new synthetic approach to phenothiazine-2-amines

  摘要：

  Elaboration of a Buchwald-Hartwig protocol for the introduction of amino functions to position 2 of the phenothiazine ring system has opened a new access to various N-alkyl and N-dienyl phenothiazines bearing secondary amines, tertiary amines, and amide moieties. Hydrolysis of the amido derivatives gave unsubstituted phenothiazine-2-amines. This protocol provides an easy access to phenothiazine-2-amines starting from the commercially available starting compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.083

文献信息

• General Method for Ni-Catalyzed C–N Cross-Couplings of (Hetero)Aryl Chlorides with Anilines and Aliphatic Amines under Homogeneous Conditions Using a Dual-Base Strategy
  作者：Roberto Silva Villatoro、Joshua R. Belfield、Hadi D. Arman、Lucas W. Hernandez、Eric M. Simmons、Zachary J. Garlets、Steven R. Wisniewski、John R. Coombs、Doug E. Frantz

  DOI：10.1021/acs.organomet.3c00419

  日期：2023.11.13

  A general method for the Ni-catalyzed Buchwald–Hartwig amination of (hetero)aryl chlorides using both anilines and aliphatic amines under homogeneous conditions has been developed. Key to the success of this method is the implementation of a dual-base strategy that utilizes an amine base combined with a soluble halide scavenger that allows for the use of a single air-stable, commercially available

  开发了一种在均相条件下使用苯胺和脂肪胺对（杂）芳基氯进行镍催化 Buchwald-Hartwig 胺化的通用方法。该方法成功的关键是实施双碱策略，该策略利用胺碱与可溶性卤化物清除剂相结合，允许使用单一空气稳定的市售 Ni(II)-预催化剂和膦配体[( R , S )-Josiphos] 组合可在低至 1.0 mol% 的催化剂负载量下促进多种（杂）芳基氯和药学相关胺亲核试剂的胺化反应。