2-(tetrahydrothiophen-2-yl)quinoline | 82081-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(tetrahydrothiophen-2-yl)quinoline
• 英文别名: 2-(Quinol-2-yl)-tetrahydrothiophen；2-(thiolan-2-yl)quinoline
• CAS: 82081-41-2
• 化学式: C₁₃H₁₃NS
• 分子量: 215.319
• InChiKey: SUVWAWWLOGXICM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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-(tetrahydrothiophen-2-yl)quinoline 在 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 N-Methyl-2-(quinol-2-yl)-tetrahydrothiophen-2-carbothioamide
  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-喹啉甲硫醇 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-(tetrahydrothiophen-2-yl)quinoline
  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

• α-Heteroarylation of Thioethers via Photoredox and Weak Brønsted Base Catalysis
  作者：Edwin Alfonzo、Sudhir M. Hande

  DOI：10.1021/acs.orglett.1c02151

  日期：2021.8.6

  thioethers to α-thio alkyl radicals and their addition to N-methoxyheteroarenium salts for the redox-neutral synthesis of α-heteroaromatic thioethers. Studies are consistent with a two-step activation mechanism, where oxidation of thioethers to sulfide radical cations by a photoredox catalyst is followed by α-C–H deprotonation by a weak Brønsted base catalyst to afford α-thio alkyl radicals. Further,

  我们报告了硫醚对 α-硫代烷基自由基的 C-H 活化以及它们与N-甲氧基杂芳鎓盐的加成，用于氧化还原中性合成 α-杂芳族硫醚。研究与两步活化机制一致，其中通过光氧化还原催化剂将硫醚氧化为硫化物自由基阳离子，然后通过弱 Brønsted 碱催化剂进行 α-C-H 去质子化以提供 α-硫代烷基自由基。此外，N-甲氧基杂芳鎓盐作为甲氧基自由基的来源，有助于α-硫代烷基自由基的产生和再生光氧化还原催化循环的牺牲氧化剂，发挥了额外的作用。
• Thiocarboxamide derivatives and their use as pharmaceuticals
  申请人：Rhone-Poulenc Sante

  公开号：US04379154A1

  公开（公告）日：1983-04-05

  Thioformamide derivatives of the formula: ##STR1## wherein R represents hydrogen or alkyl of 1 through 4 carbon atoms, and (i) Het represents a heterocyclic radical selected from pyrid-3-yl, pyrid-4-yl, pyridazinyl, pyrazinyl, pyrimidinyl, quinolyl, imidazolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, X represents sulphur or oxygen and Y represents sulphur or oxygen, a valency bond or methylene, or (ii) Het represents pyrid-2-yl, X represents sulphur or oxygen and Y represents sulphur or oxygen or methylene, or (iii) Het represents pyrid-2-yl, X represents oxygen and Y represents a valency bond, are new compounds possessing useful pharmacological properties. They are particularly useful in the treatment of gastrointestinal ulcers and in the treatment of hypertension, depending on the definition of the symbol Het.

  式为：##STR1## 其中R代表氢或1至4个碳原子的烷基，(i)Het代表从吡啶-3-基、吡啶-4-基、吡嗪基、吡咯嗪基、嘧啶基、喹啉基、咪唑基、萘啶基、喹喔啉基和喹唑啉基中选出的杂环基，X代表硫或氧，Y代表硫或氧、一个价键或亚甲基，或者(ii) Het代表吡啶-2-基，X代表硫或氧，Y代表硫或氧或亚甲基，或者(iii) Het代表吡啶-2-基，X代表氧，Y代表一个价键的新化合物具有有用的药理学性质。它们在治疗胃肠溃疡和高血压方面特别有用，具体取决于符号Het的定义。
• Rare-Earth Y(OTf)₃ Catalyzed Coupling Reaction of Ethers with Azaarenes
  作者：Yue-Hua Wu、Nai-Xing Wang、Tong Zhang、Lei-Yang Zhang、Xue-Wang Gao、Bao-Cai Xu、Yalan Xing、Jian-Yi Chi

  DOI：10.1021/acs.orglett.9b02763

  日期：2019.9.20

  Rare-earth catalysis has become a hot topic in the field of catalytic organic reaction. Chain ethers mostly have lower reactivity and lower boiling points which limited their reaction scope. Herein, we found a rare-earth Y(OTf)(3) can catalyze the coupling reaction of ethers especially chain ethers and thioethers with azaarenes. This protocol features simple operations, a broad substrate scope (31 examples), moderate to good yields (up to 85%), and atom economy.
• 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：——
• US4379154A
  申请人：——

  公开号：US4379154A

  公开（公告）日：1983-04-05