3-chloro-6-(1-methyl-4-piperidyl)-6H-dibenz-1,4-oxathiepin | 96122-57-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-chloro-6-(1-methyl-4-piperidyl)-6H-dibenz-1,4-oxathiepin
• 英文别名: 4-(8-chloro-11H-dibenzo[b,e][1,4]oxathiepin-11-yl)-1-methylpiperidine；4-(3-chloro-6H-benzo[b][4,1]benzoxathiepin-6-yl)-1-methylpiperidine
• CAS: 96122-57-5
• 化学式: C₁₉H₂₀ClNOS
• 分子量: 345.893
• InChiKey: KGFKMQPKZITFIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [2-(4-Chloro-2-fluoro-phenylsulfanyl)-phenyl]-(1-methyl-piperidin-4-yl)-methanol 以64%的产率得到
  参考文献：
  名称：

  SINDELAR, K.;HOLUBEK, J.;RYSKA, M.;DLABAC, A.;VALCHAR, M.;METYSOVA, J.;PR+, COLLECT. CZECHOSL. CHEM. COMMUN., 1984, 49, N 11, 2531-2540

  摘要：

  DOI：

文献信息

• Tricyclic compounds containing two chalcogen atoms in the central seven-membered rings as potential drugs: Synthesis of 3-chloro-6-(1-methyl-4-piperidyl)-6H-dibenz[b,e]-1,4-oxathiepin and 6-oxodibenz[b,e]-1,4-oxathiepin-2-acetic acid
  作者：Karel Šindelář、Jiří Holubek、Miroslav Ryska、Antonín Dlabač、Martin Valchář、Jiřina Metyšová、Miroslav Protiva

  DOI：10.1135/cccc19842531

  日期：——

  2-(4-hloro-2-fluorophenylthio)benzaldehyde (IIa) was subjected to treatment with 1-methyl-4-piperidylmagnesium chloride and the resulting secondary alcohol IIIa was cyclized with sodium hydride to the title compound Ia. In this synthesis, two by-products were isolated and identified as compounds IV and VIa. Repeating the synthesis of compound Ib by a similar way led to isolation of Vb and VII. Reaction of thiosalicylic acid with (3-iodo-4-methoxyphenyl)acetic acid in boiling aqueous potassium hydroxide in the presence of copper gave the methoxy diacid IX which was demethylated with hydrogen bromide in acetic acid to the hydroxy diacid X. Heating with acetic anhydride afforded the title lactone acid VIII. Compound Ia is an almost noncataleptic neuroleptic with a rather low antidopaminergic activity in the test of influencing the dopamine turnover and metabolism in the rat brain striatum. The acid VIII showed some antiinflammatory activity in the test of carrageenan-induced edema of rat's paw.

  2-(4-氯-2-氟苯硫基)苯甲醛（IIa）经过与1-甲基-4-哌啶基镁氯化物反应后，生成了二级醇（IIIa），随后与氢化钠发生环化反应，形成了目标化合物（Ia）。在这个合成过程中，分离并鉴定出了两种副产物，分别为化合物IV和VIa。通过类似的方法重复合成化合物Ib，得到了Vb和VII。将硫代水杨酸与（3-碘-4-甲氧基苯基）乙酸在沸腾的氢氧化钾水溶液中在铜的存在下反应，得到了甲氧二酸（IX），然后用乙酸中的溴化氢脱甲基化，生成了羟二酸（X）。与乙酸酐加热后得到了标题内酯酸（VIII）。化合物Ia是一种几乎无肌阵挛作用的神经阻滞剂，在大鼠脑纹状体的多巴胺转运和代谢影响测试中具有较低的抗多巴胺活性。酸VIII在大鼠爪介苔藓素诱导的水肿测试中显示了一定的抗炎活性。
• PROTIVA, MIROSLAV;SINDELAR, KAREL;DLABAC, ANTONIN;VALCHAR, MARTIN
  作者：PROTIVA, MIROSLAV、SINDELAR, KAREL、DLABAC, ANTONIN、VALCHAR, MARTIN

  DOI：——

  日期：——
• SINDELAR, K.;HOLUBEK, J.;RYSKA, M.;DLABAC, A.;VALCHAR, M.;METYSOVA, J.;PR+, COLLECT. CZECHOSL. CHEM. COMMUN., 1984, 49, N 11, 2531-2540
  作者：SINDELAR, K.、HOLUBEK, J.、RYSKA, M.、DLABAC, A.、VALCHAR, M.、METYSOVA, J.、PR+

  DOI：——

  日期：——