4-fluoro-2-thiophenylaniline | 329216-96-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-fluoro-2-thiophenylaniline
• 英文别名: 4-fluoro-2-(phenylthio)aniline；4-Fluoro-2-phenylsulfanylaniline
• CAS: 329216-96-8
• 化学式: C₁₂H₁₀FNS
• 分子量: 219.283
• InChiKey: SWLWFGHLXXGBNA-UHFFFAOYSA-N

物化性质

• 沸点：
  339.8±32.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-fluoro-2-thiophenylaniline 在 三氯化铝 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 邻二氯苯 为溶剂， 反应 18.0h， 生成 6-Chloro-2-fluorobenzo[b][1,4]benzothiazepine
  参考文献：
  名称：

  Behavioral Approach to Nondyskinetic Dopamine Antagonists:  Identification of Seroquel

  摘要：

  A great need exists for antipsychotic drugs which will not induce extrapyramidal symptoms (EPS) and tardive dyskinesias (TDs). These side effects are deemed to be a consequence of nonselective blockade of nigrostriatal and mesolimbic dopamine D2 receptors. Nondyskinetic clozapine (1) is a low-potency D2 dopamine receptor antagonist which appears to act selectively in the mesolimbic area. In this work dopamine antagonism was assessed in two mouse behavioral assays: antagonism of apomorphine-induced climbing and antagonism of apomorphine-induced disruption of swimming. The potential for the liability of dyskinesias was determined in haloperidol-sensitized Cebus monkeys. Initial examination of a few close cogeners of 1 enhanced confidence in the Cebus model as a predictor of dyskinetic potential. Considering dibenzazepines, 2 was not dyskinetic whereas 2a was dyskinetic. Among dibenzodiazepines, 1 did not induce dyskinesias where as its N-2-(2-hydroxyethoxy)ethyl analogue 3 was dyskinetic. The emergence of such distinctions presented an opportunity. Thus, aromatic and N-substituted analogues of 6-(piperazin-1-yl)-11H-dibenz[b,e]azepines and 11-(piperazin-1-yl)dibenzo[b,f][1,4]thiazepines and -oxazepines were prepared and evaluated. 11-(4-[2-(2-Hydroxyethoxy)ethyl]piperazin-1-yl)dibenzo[b,f][1,4]thiazepine (23) was found to be an apomorphine antagonist comparable to clozapine. It was essentially nondyskinetic in the Cebus model. With 23 as a platform, a number of N-substituted analogues were found to be good apomorphine antagonists but all were dyskinetic.

  DOI：

  10.1021/jm000242+
• 作为产物：
  描述：

  S-苯基硫代苯基砜 在 叔丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 4-fluoro-2-thiophenylaniline
  参考文献：
  名称：

  Behavioral Approach to Nondyskinetic Dopamine Antagonists:  Identification of Seroquel

  摘要：

  A great need exists for antipsychotic drugs which will not induce extrapyramidal symptoms (EPS) and tardive dyskinesias (TDs). These side effects are deemed to be a consequence of nonselective blockade of nigrostriatal and mesolimbic dopamine D2 receptors. Nondyskinetic clozapine (1) is a low-potency D2 dopamine receptor antagonist which appears to act selectively in the mesolimbic area. In this work dopamine antagonism was assessed in two mouse behavioral assays: antagonism of apomorphine-induced climbing and antagonism of apomorphine-induced disruption of swimming. The potential for the liability of dyskinesias was determined in haloperidol-sensitized Cebus monkeys. Initial examination of a few close cogeners of 1 enhanced confidence in the Cebus model as a predictor of dyskinetic potential. Considering dibenzazepines, 2 was not dyskinetic whereas 2a was dyskinetic. Among dibenzodiazepines, 1 did not induce dyskinesias where as its N-2-(2-hydroxyethoxy)ethyl analogue 3 was dyskinetic. The emergence of such distinctions presented an opportunity. Thus, aromatic and N-substituted analogues of 6-(piperazin-1-yl)-11H-dibenz[b,e]azepines and 11-(piperazin-1-yl)dibenzo[b,f][1,4]thiazepines and -oxazepines were prepared and evaluated. 11-(4-[2-(2-Hydroxyethoxy)ethyl]piperazin-1-yl)dibenzo[b,f][1,4]thiazepine (23) was found to be an apomorphine antagonist comparable to clozapine. It was essentially nondyskinetic in the Cebus model. With 23 as a platform, a number of N-substituted analogues were found to be good apomorphine antagonists but all were dyskinetic.

  DOI：

  10.1021/jm000242+

文献信息

• DIBENZOTHIAZEPINE DERIVATIVES AND USES THEREOF - 424
  申请人：Brown Dean

  公开号：US20090318415A1

  公开（公告）日：2009-12-24

  Compounds the following formula: wherein Z is as described in the specification, pharmaceutically acceptable salts thereof, compositions comprising the same, and methods of treating bipolar disorder, an anxiety disorder, a mood disorder or schizophrenia or other psychotic disorder with said compounds.

  合成以下公式：其中Z如规范中所述，其药学上可接受的盐，包含相同物质的组合物，以及使用该化合物治疗双相情感障碍、焦虑障碍、情绪障碍或精神分裂症或其他精神障碍的方法。
• Dibenzothiazepine Derivatives and Use Thereof
  申请人：Brown Dean

  公开号：US20110160184A1

  公开（公告）日：2011-06-30

  Compounds the following formula: wherein Z is as described in the specification, pharmaceutically acceptable salts thereof, compositions comprising the same, and methods of treating bipolar disorder, an anxiety disorder, a mood disorder or schizophrenia or other psychotic disorder with said compounds.

  以下是化合物的公式：其中Z如说明书所述，其药学上可接受的盐，包含其的组合物，以及使用该化合物治疗双相情感障碍、焦虑障碍、情感障碍或精神分裂症或其他精神障碍的方法。
• Arylthiolation of Arylamine Derivatives with (Arylthio)- pyrrolidine-2,5-diones
  作者：Hua Tian、Haijun Yang、Changjin Zhu、Hua Fu

  DOI：10.1002/adsc.201400929

  日期：2015.2.9

  AbstractA simple and efficient method for arylthiolation of arylamines has been developed. The protocol uses (arylthio)pyrrolidine‐2,5‐diones as the arylthiolating reagents, acetonitrile as the solvent, and no catalyst and additive are required, which avoids contamination from the transition metal catalysts in the target products. Therefore, the present method should provide a convenient, efficient and practical strategy for the synthesis of other aryl sulfides.magnified image
• DIBENZOTHIAZEPINE DERIVATIVE AND USE THEREOF
  申请人：AstraZeneca AB

  公开号：EP2307389B1

  公开（公告）日：2013-01-23
• DIBENZOTHIAZEPINE DERIVATIVES AND USE THEREOF
  申请人：AstraZeneca AB

  公开号：EP2307389A1

  公开（公告）日：2011-04-13