3-氟-10H-吩噻嗪 | 397-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 中文名称: 3-氟-10H-吩噻嗪
• 英文名称: 3-fluoro-10H-phenothiazine
• 英文别名: 3-fluoro-10H-phenothiazine；3-fluoro-phenothiazine；3-Fluor-phenothiazin
• CAS: 397-59-1
• 化学式: C₁₂H₈FNS
• 分子量: 217.267
• InChiKey: PNDZYFUALQXWOY-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177 °C
• 沸点：
  362.9±31.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(氯甲基)-1-甲基哌啶 、 3-氟-10H-吩噻嗪 在 lithium hexamethyldisilazane 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.25h， 生成 3-Fluoro-10-[(1-methylpiperidin-3-yl)methyl]phenothiazine
  参考文献：
  名称：

  Synthesis and antitubercular activity of phenothiazines with reduced binding to dopamine and serotonin receptors

  摘要：

  Analogs of the psychotropic phenothiazines were synthesized and examined as antitubercular agents against Mycobacterium tuberculosis H37Rv. The compounds were subsequently counter-screened for binding to the dopaminergic-receptor subtypes D1, D2, D3 and the serotonergic-receptor subtypes 5-HT1A, 5-HT2A, and 5-HT2C. The most active compounds showed MICs from 2 to 4 mu g/mL and had overall reduced binding to the dopamine and serotonin receptors compared to chlorpromazine and trifluoperazine. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.064
• 作为产物：
  描述：

  formic acid-[2-(4-fluoro-2-nitro-phenylsulfanyl)-anilide] 在 sodium hydroxide 、 丙酮 作用下， 生成 3-氟-10H-吩噻嗪
  参考文献：
  名称：

  THE PREPARATION OF SOME FLUORO- AND TRIFLUOROMETHYL-PHENOTHIAZINES, AND SOME OBSERVATIONS REGARDING DETERMINATION OF THEIR STRUCTURE BY INFRARED SPECTROSCOPY¹

  摘要：

  DOI：

  10.1021/jo01128a018

文献信息

• Potassium carbonate-mediated tandem C–S and C–N coupling reaction for the synthesis of phenothiazines under transition-metal-free and ligand-free conditions
  作者：San Wu、Wei-Ye Hu、Song-Lin Zhang

  DOI：10.1039/c6ra01295g

  日期：——

  An efficient potassium carbonate-mediated tandem C–S and C–N coupling reaction between N-(2-iodophenyl)acetamides and 2-halo-benzenethiols has been developed. This protocol affords a simple and efficient approach for the construction of phenothiazine derivatives without the need for addition of transition-metal catalyst or ligand for the first time. Furthermore, the reaction can be easily performed

  已经开发出一种有效的碳酸钾介导的N-（2-碘苯基）乙酰胺与2-卤代苯硫醇之间的串联C–S和C–N偶联反应。该方案为构建吩噻嗪衍生物提供了一种简单而有效的方法，而无需首次添加过渡金属催化剂或配体。此外，该反应可以容易地大规模进行。
• Synthesis of phenothiazines from cyclohexanones and 2-aminobenzenethiols under transition-metal-free conditions
  作者：Yunfeng Liao、Pengcheng Jiang、Shanping Chen、Fuhong Xiao、Guo-Jun Deng

  DOI：10.1039/c3ra43989e

  日期：——

  A convenient method for the synthesis of various substituted phenothiazines from cyclohexanones and 2-aminobenzenethiols using molecular oxygen as hydrogen acceptor in the absence of transition-metals is described. For the first time cyclohexanones were used as coupling partners for the construction of phenothiazines.

  一种便利的方法被描述用于合成各种取代的苯噻嗪，该方法采用环己酮和2-氨基苯硫醇，以分子氧作为氢受体，且不需要过渡金属。这是第一次将环己酮用作构建苯噻嗪的偶联伙伴。
• Transition-metal-free synthesis of phenothiazines from S-2-acetamidophenyl ethanethioate and <i>ortho</i>-dihaloarenes
  作者：Yue Zhou、Qingle Zeng、Li Zhang

  DOI：10.1080/00397911.2017.1281959

  日期：2017.4.3

  ABSTRACT An efficient cesium carbonate-mediated synthesis of phenothiazine derivatives from S-2-acetamidophenyl ethanethioates and ortho-dihaloarenes has been developed. This protocol affords an efficient approach for the construction of phenothiazine derivatives without the need of transition-metal catalyst or ligand. A plausible mechanism is proposed. GRAPHICAL ABSTRACT

  摘要已开发出一种高效的碳酸铯介导的 S-2-乙酰氨基苯基乙硫醚和邻二卤代芳烃合成吩噻嗪衍生物。该协议提供了一种无需过渡金属催化剂或配体即可构建吩噻嗪衍生物的有效方法。提出了一个合理的机制。图形概要
• Phenothiazine derivatives, compositions thereof and methods of
  申请人：Kefalas A/S

  公开号：US03966930A1

  公开（公告）日：1976-06-29

  Fluoro-substituted phenothiazine derivatives as well as their non-toxic pharmaceutically acceptable acid addition salts having pronounced neuroleptic properties and a relatively low degree of undesired side effects, a method for the preparation of said derivatives, pharmaceutical compositions containing same which may be administered to animals, including human beings, orally or parenterally.

  氟代苯并噻嗪衍生物及其无毒的药学可接受的酸盐，具有明显的神经抑制作用和相对较低的不良副作用，制备该衍生物的方法，含有该衍生物的制剂可经口或经肌肉注射给动物，包括人类。
• FORMATION AND OXIDATION OF SOME PHENOTHIAZINE DERIVATIVES
  作者：NATHAN L. SMITH

  DOI：10.1021/jo01143a011

  日期：1951.3