2-(6-methylpyrid-2-yl)tetrahydrothiophene | 76732-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(6-methylpyrid-2-yl)tetrahydrothiophene
• 英文别名: 2-Methyl-6-(thiolan-2-yl)pyridine
• CAS: 76732-78-0
• 化学式: C₁₀H₁₃NS
• 分子量: 179.286
• InChiKey: OQGOBPLAUUHRTM-UHFFFAOYSA-N

物化性质

• 沸点：
  300.8±42.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(6-methylpyrid-2-yl)tetrahydrothiophene 在 正丁基锂 、 氨 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2-(6-Methyl-pyridin-2-yl)-tetrahydro-thiophene-2-carbothioic acid amide
  参考文献：
  名称：

  Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide

  摘要：

  New thioamide derivatives of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (29) and related compounds (in which the tetrahydrothiophene ring was replaced by tetrahydrothiopyran, tetrahydrofuran, 1,3-dithiane, or 1,3-oxathiane and where the pyridine ring was replaced by other nitrogen heterocycles) were synthesized and tested for their antisecretory and antiulcer activities. These thioamides were prepared according to one of the following methods: reaction of an isothiocyanate with the carbanion of the corresponding cyclic precursor (for secondary thioamides); reaction of ammonia or an amine with the dithio ester prepared from the same precursor (for primary, secondary, and tertiary thioamides). These thioamides were evaluated by the Shay method to measure their antisecretory activity and by the stress-induced-ulcer method to test their antiulcer activity. Structure-activity relationships are discussed. N-Methyl-2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (R.P. 40749, 30) exhibited activities that were at least 10 times higher than those reported for cimetidine.

  DOI：

  10.1021/jm00384a004
• 作为产物：
  描述：

  2-(6-methylpyrid-2-ylmethyl)isothiourea dihydrochloride 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 2-(6-methylpyrid-2-yl)tetrahydrothiophene
  参考文献：
  名称：

  Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide

  摘要：

  New thioamide derivatives of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (29) and related compounds (in which the tetrahydrothiophene ring was replaced by tetrahydrothiopyran, tetrahydrofuran, 1,3-dithiane, or 1,3-oxathiane and where the pyridine ring was replaced by other nitrogen heterocycles) were synthesized and tested for their antisecretory and antiulcer activities. These thioamides were prepared according to one of the following methods: reaction of an isothiocyanate with the carbanion of the corresponding cyclic precursor (for secondary thioamides); reaction of ammonia or an amine with the dithio ester prepared from the same precursor (for primary, secondary, and tertiary thioamides). These thioamides were evaluated by the Shay method to measure their antisecretory activity and by the stress-induced-ulcer method to test their antiulcer activity. Structure-activity relationships are discussed. N-Methyl-2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (R.P. 40749, 30) exhibited activities that were at least 10 times higher than those reported for cimetidine.

  DOI：

  10.1021/jm00384a004

文献信息

• 2-(Pyrid-2-yl)tetrahydrothiophene derivatives
  申请人：Rhone-Poulenc Industries

  公开号：US04272534A1

  公开（公告）日：1981-06-09

  Compounds of the formula: ##STR1## wherein R represents hydrogen or alkyl of 1 through 4 carbon atoms, and R.sub.1 and R.sub.2 represent hydrogen or alkyl of 1 through 15 carbon atoms, or alkyl of 1 through 15 carbon atoms substituted by one substituent selected from (i) hydroxy, (ii) alkylamino in which the alkyl radical is of 1 through 4 carbon atoms, (iii) dialkylamino in which the alkyl radicals are of 1 through 4 carbon atoms, (iv) phenyl, (v) carboxy, and (vi) alkoxycarbonyl in which the alkoxy radical is of 1 through 4 carbon atoms, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached represent a five- or six-membered heterocyclic radical, are new compounds. They possess pharmacological properties and are particularly useful in the treatment of gastro-intestinal ulcers.

  式子为：##STR1## 其中 R 代表氢或1至4个碳原子的烷基，R.sub.1 和 R.sub.2 代表氢或1至15个碳原子的烷基，或1至15个碳原子的烷基被选自以下一种取代基取代：(i) 羟基，(ii) 烷基胺，其中烷基基团为1至4个碳原子，(iii) 二烷基胺，其中烷基基团为1至4个碳原子，(iv) 苯基，(v) 羧基，以及 (vi) 烷氧羰基，其中烷氧基团为1至4个碳原子，或 R.sub.1 和 R.sub.2 与它们所连接的氮原子共同表示五元或六元杂环基团，这些化合物是新的。它们具有药理学特性，特别适用于治疗胃肠溃疡。
• ALOUP J. C.; BOUCHAUDON J.; FARGE D.; JAMES C.; DEREGNAUCOURT J.; HARDY-H+, J. MED. CHEM., 30,(1987) N 1, 24-29
  作者：ALOUP J. C.、 BOUCHAUDON J.、 FARGE D.、 JAMES C.、 DEREGNAUCOURT J.、 HARDY-H+

  DOI：——

  日期：——
• US4272534A
  申请人：——

  公开号：US4272534A

  公开（公告）日：1981-06-09
• Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide
  作者：Jean-Claude Aloup、Jean Bouchaudon、Daniel Farge、Claude James、Jean Deregnaucourt、Monique Hardy-Houis

  DOI：10.1021/jm00384a004

  日期：1987.1

  New thioamide derivatives of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (29) and related compounds (in which the tetrahydrothiophene ring was replaced by tetrahydrothiopyran, tetrahydrofuran, 1,3-dithiane, or 1,3-oxathiane and where the pyridine ring was replaced by other nitrogen heterocycles) were synthesized and tested for their antisecretory and antiulcer activities. These thioamides were prepared according to one of the following methods: reaction of an isothiocyanate with the carbanion of the corresponding cyclic precursor (for secondary thioamides); reaction of ammonia or an amine with the dithio ester prepared from the same precursor (for primary, secondary, and tertiary thioamides). These thioamides were evaluated by the Shay method to measure their antisecretory activity and by the stress-induced-ulcer method to test their antiulcer activity. Structure-activity relationships are discussed. N-Methyl-2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (R.P. 40749, 30) exhibited activities that were at least 10 times higher than those reported for cimetidine.