3-(n-butyl)tetrahydrothiophene | 1551-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: 3-(n-butyl)tetrahydrothiophene
• 英文别名: 3-butyltetrahydrothiophene；3-butylthiolane；3-butyl-tetrahydro-thiophene；3-Butyl-tetrahydro-thiophen；3-Butyl-thiacyclopentan；3-n-Butyl-thiophan
• CAS: 1551-24-2
• 化学式: C₈H₁₆S
• 分子量: 144.281
• InChiKey: WEWIGXOEGOJCIE-UHFFFAOYSA-N

物化性质

• 沸点：
  209.5-209.9 °C(Press: 733 Torr)
• 密度：
  0.9271 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(n-butyl)tetrahydrothiophene 在 sodium periodate 作用下， 以 水 为溶剂， 以62%的产率得到3-butylthiolane 1-oxide
  参考文献：
  名称：

  Inhibition of liver alcohol dehydrogenase and ethanol metabolism by 3-substituted thiolane 1-oxides

  摘要：

  3-Substituted thiolane 1-oxides (methyl, n-butyl, n-hexyl, and phenyl) were prepared and tested as inhibitors of horse, monkey, and rat liver alcohol dehydrogenases and of ethanol metabolism in rats. These compounds inhibit alcohol oxidation in an uncompetitive manner with respect to ethanol as a varied substrate. Lengthening the alkyl substituent increased the inhibitory potency because of tighter binding in the hydrophobic substrate binding pocket of the alcohol dehydrogenases. Thus, the 3-hexyl derivative was the most potent inhibitor of the purified rat liver alcohol dehydrogenase, with a Kii value of 0.13 microM. The 3-butyl derivative was the best inhibitor of ethanol metabolism in rats, with a Kii value of 11 mumol/kg. The acute toxicity in mice of the butyl derivative was 1.4 mmol/kg. Since high concentrations of alcohol do not prevent the inhibitory effects of these compounds, they may be particularly useful for preventing poisoning by methanol or ethylene glycol.

  DOI：

  10.1021/jm00379a009
• 作为产物：
  描述：

  2-butyl-1,4-diiodobutane 在 sodium sulfide 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 3-(n-butyl)tetrahydrothiophene
  参考文献：
  名称：

  Inhibition of liver alcohol dehydrogenase and ethanol metabolism by 3-substituted thiolane 1-oxides

  摘要：

  3-Substituted thiolane 1-oxides (methyl, n-butyl, n-hexyl, and phenyl) were prepared and tested as inhibitors of horse, monkey, and rat liver alcohol dehydrogenases and of ethanol metabolism in rats. These compounds inhibit alcohol oxidation in an uncompetitive manner with respect to ethanol as a varied substrate. Lengthening the alkyl substituent increased the inhibitory potency because of tighter binding in the hydrophobic substrate binding pocket of the alcohol dehydrogenases. Thus, the 3-hexyl derivative was the most potent inhibitor of the purified rat liver alcohol dehydrogenase, with a Kii value of 0.13 microM. The 3-butyl derivative was the best inhibitor of ethanol metabolism in rats, with a Kii value of 11 mumol/kg. The acute toxicity in mice of the butyl derivative was 1.4 mmol/kg. Since high concentrations of alcohol do not prevent the inhibitory effects of these compounds, they may be particularly useful for preventing poisoning by methanol or ethylene glycol.

  DOI：

  10.1021/jm00379a009

文献信息

• Zirconium-catalyzed preparation of aluminacyclopentanes and synthesis of five-membered carbo- and heterocycles
  作者：Usein M Dzhemilev、Askhat G Ibragimov、Ruslan R Gilyazev、Leila O Khafizova

  DOI：10.1016/j.tet.2003.10.082

  日期：2004.2

  Novel ‘one-pot’ catalytic methods for the synthesis of cyclopentanols, tetrahydrothiophenes, silacyclopentanes and phospholanes are based on successive transformations of olefins and organoaluminium compounds (R2AlR′) in the presence of Cp2ZrCl2 catalyst. In situ generated aluminacyclopentanes serve as common intermediates in these processes.

  用于合成环戊醇，四氢噻吩，硅环戊烷和膦酸酯的新型“一锅法”催化方法是基于在Cp 2 ZrCl 2催化剂存在下烯烃和有机铝化合物（R 2 AlR'）的连续转化。原位生成的氧化铝环戊烷在这些过程中用作常见的中间体。
• Inhibition of alcohol metabolism by tetramethylene sulfoxides
  申请人：University of Iowa Research Foundation

  公开号：US04482568A1

  公开（公告）日：1984-11-13

  Tetramethylene sulfoxide and its substituted derivatives have been found to be exceptionally potent inhibitors of oxidation of alcohols by liver alcohol dehydrogenases.

  四亚甲基亚砜及其衍生物已被发现是肝脏酒精脱氢酶氧化醇的非常强效抑制剂。
• Process for the carbonylation of alkanols and/or ethers
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0042633A1

  公开（公告）日：1981-12-30

  Process forthe carbonylation of alkanols and/or ethers at elevated temperature and pressure in the presence of a Group VIII metal compound and pentachlorobenzenethiol and/or salts thereof, using a pentachlorobenzenethiol compound : Group VIII metal compound molar ratio of not more than 10. The process is of special interest for the production of methyl acetate from methanol using an active, iodine-free catalytic system.

  在第八族金属化合物和五氯苯硫酚和/或其盐存在下，在高温高压下对烷 醇和/或醚进行羰基化的工艺，使用的五氯苯硫酚化合物：第八族金属化合物摩尔比不超过 10。该工艺特别适用于使用活性无碘催化体系从甲醇中生产醋酸甲酯。
• Process for the preparation of carbonate esters
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0071286A1

  公开（公告）日：1983-02-09

  A process for the oxidative carbonylatioh of an alcohol to produce a carbonate, which comprises reacting together carbon monoxide, oxygen and an alcohol, in the presence of a copper compound and in the presence of a sulphone.

  一种将醇氧化羰基化生成碳酸盐的工艺，包括一氧化碳、氧气和醇在铜化合物和砜的存在下一起反应。
• Process for hydration of olefins
  申请人：TOA NENRYO KOGYO KABUSHIKI KAISHA

  公开号：EP0127486A1

  公开（公告）日：1984-12-05

  An improved process for producing an alcohol by hydrating an olefin wherein the improvement comprises hydrating an olefin in the presence of a hydrogen-type catalyst having a silica/alumina molar ratio of 20 to 500 and a solvent using either: A. hydrogen-type mordenite or hydrogen-type zeolite Y, and a sulfone; or B. hydrogen-type crystalline aluminosilicate in which the entrance of the main void is formed by a 10-membered or 12-membered oxygen ring, and a C2 to C5 oxy acid or the lactones, lactides, methyl or ethyl esters thereof.

  一种通过水合烯烃生产醇的改进工艺，其改进包括在二氧化硅/氧化铝摩尔比为 20 至 500 的氢型催化剂和溶剂存在下水合烯烃： A. 氢型莫来石或氢型沸石 Y，以及砜；或 B. 氢型结晶铝硅酸盐，其中主空隙入口由 10 元或 12 元氧环和 C2 至 C5 氧酸或其内酯、内酯、甲基或乙基酯形成。