5-bromo-2-(4-isopropylphenylthio)phenylacetonitril | 91528-04-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-bromo-2-(4-isopropylphenylthio)phenylacetonitril
• 英文别名: 2-[5-bromo-2-(4-propan-2-ylphenyl)sulfanylphenyl]acetonitrile
• CAS: 91528-04-0
• 化学式: C₁₇H₁₆BrNS
• 分子量: 346.291
• InChiKey: YVTUUJMQTPELKR-UHFFFAOYSA-N

物化性质

• 沸点：
  455.5±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(4-isopropylphenylthio)phenylacetonitril 生成 2-<5-bromo-2-(4-isopropylphenylthio)phenyl>acetic acid
  参考文献：
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  摘要：

  DOI：
• 作为产物：
  描述：

  5-bromo-2-(4-isopropylphenylthio)benzyl chloride 生成 5-bromo-2-(4-isopropylphenylthio)phenylacetonitril
  参考文献：
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  摘要：

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文献信息

• Noncataleptic neuroleptic agents: 2-Halogeno-8-isopropyl-10-piperazino-10,11-dihydrodibenzo[b,f,]thiepins
  作者：Zdeněk Polívka、Jiří Jílek、Jiří Holubek、Emil Svátek、Antonín Dlabač、Martin Valchář、Miroslav Protiva

  DOI：10.1135/cccc19840086

  日期：——

  Reactions of 5-fluoro, 5-chloro- and 5-bromo-2-iodobenzoic acid with 4-isopropylthiophenol in solutions of potassium hydroxide in the presence of copper gave the acids VIIabc which were transformed via the intermediates VIIIabc-Xabc to 2-[5-halogeno-2-(4-isopropylphenylthio)-phenyl]acetic acids XIabc. Their cyclization with polyphosphoric acid resulted in 2-halogeno-8-isopropyldibenzo[b,f]thiepin-10(11H)-ones XIIabc.The 2-iodo ketone XIId was obtained from 2-(2-chloro-5-nitrophenyl)acetic acid by treatment with 4-isopropylthiophenol, by the following reduction of the resulting nitro acid XIe with hydrazine to the amino acid XIf, by its cyclization to the amino ketone XIIf and finally by its diazotization and reaction with potassium iodide. The ketones XIIa-d were reduced to the alcohols XIIIa-d giving by treatment with hydrogen chloride the chloro compounds XIVa-d. Substitution reactions with 1-methylpiperazine and 1-(2-hydroxyethyl)piperazine afforded the title compounds Vabc and VIa-d. Only the fluoro derivatives Va and VIa showed a clear cataleptic activity in rats. The other compounds are very little active in this line and the iodo derivative VId was found to be completely inactive in a high oral dose, but it revealed an intensive antidopaminergic action in biochemical tests. By its pharmacological profile it resembles the known noncataleptic neuroleptic agent clozapine.

  5-氟、5-氯和5-溴-2-碘苯甲酸与4-异丙基硫酚在氢氧化钾溶液中，在铜的存在下反应，生成了酸VIIabc，这些酸通过中间体VIIIabc-Xabc转化为2-[5-卤代-2-(4-异丙基苯硫基)苯基]乙酸XIabc。它们与多磷酸的环化反应产生了2-卤代-8-异丙基二苯并[b,f]噻吩-10(11H)-酮XIIabc。2-碘代酮XIId是通过2-(2-氯-5-硝基苯基)乙酸与4-异丙基硫酚反应，随后将生成的硝基酸XIe用肼还原为氨基酸XIf，再通过其环化成氨基酮XIIf，最后通过重氮化和与碘化钾反应得到的。酮XIIa-d被还原为醇XIIIa-d，通过与氯化氢处理得到氯化物XIVa-d。与1-甲基哌嗪和1-(2-羟乙基)哌嗪的取代反应得到了标题化合物Vabc和VIa-d。只有氟代衍生物Va和VIa在大鼠中显示出明显的僵住活性。其他化合物在这方面活性很低，碘代衍生物VId在高口服剂量下被发现完全无活性，但它显示出强烈的抗多巴胺能作用在生化测试中。根据其药理学特征，它类似于已知的非僵住性神经安定剂氯氮平。
• POLIVKA, Z.;JILEK, J.;HOLUBEK, J.;SVATEK, E.;DLABAC, A.;VALCHAR, M.;PROTI+, COLLECT. CZECHOSL. CHEM. COMMUN., 1984, 49, N 1, 86-109
  作者：POLIVKA, Z.、JILEK, J.、HOLUBEK, J.、SVATEK, E.、DLABAC, A.、VALCHAR, M.、PROTI+

  DOI：——

  日期：——
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  作者：PROTIVA M.、 POLIVKA Z.、 DLABAC A.、 VALCHAR M.

  DOI：——

  日期：——