3-苯基四氢噻吩 | 16766-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-苯基四氢噻吩
• 英文名称: 3-phenyltetrahydrothiophene
• 英文别名: 3-Phenylthiolane
• CAS: 16766-62-4
• 化学式: C₁₀H₁₂S
• 分子量: 164.271
• InChiKey: MMBMCZZLHYNDRS-UHFFFAOYSA-N

物化性质

• 熔点：
  6 °C
• 沸点：
  112-113 °C(Press: 5 Torr)
• 密度：
  1.1009 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-苯基四氢噻吩 在 sodium periodate 作用下， 以 水 为溶剂， 以56%的产率得到3-Phenyl-tetrahydro-thiophene 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-phenylbut-3-en-2-ol 在 三乙基硅烷 、 氢溴酸 、 溶剂黄146 、 二甲基亚砜 、 三氟乙酸 、 potassium bromide 作用下， 以 硝基甲烷 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 44.0h， 生成 3-苯基四氢噻吩
  参考文献：
  名称：

  用 DMSO 构建（二氢）噻吩的氧化还原发散性

  摘要：

  我们在此报告了二氢噻吩、噻吩和溴噻吩的氧化还原发散结构，它们分别来自容易获得的烯丙醇、二甲基亚砜 (DMSO) 和 HBr。该策略可用于生物活性和功能分子的可编程和简洁合成。

  DOI：

  10.1002/anie.202109026

文献信息

• Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides
  作者：Franz-Lucas Haut、Christoph Habiger、Klaus Speck、Klaus Wurst、Peter Mayer、Johannes Nepomuk Korber、Thomas Müller、Thomas Magauer

  DOI：10.1021/jacs.9b07729

  日期：2019.8.28

  Here we present a comprehensive study on the [3+2]-cycloaddition of thiocarbonyl ylides with a wide variety of alkenes and alkynes. The obtained dihydro- and tetrahydrothiophenes products serve as exceptionally versatile intermediates providing access to thiophenes, dienes, dendralenes, and vic-quarternary carbon centers. The use of high-pressure conditions enables thermally unstable, sterically encumbered

  在这里，我们对硫代羰基叶立德与各种烯烃和炔烃的[3+2]-环加成进行了全面的研究。所获得的二氢和四氢噻吩产品作为用途极其广泛的中间体，提供了获得噻吩、二烯、树枝烯和八元碳中心的途径。高压条件的使用使得热不稳定、空间阻碍或中等反应性的底物能够在温和条件下进行环加成，从而将产率提高高达 58%。此外，我们还通过药物 NGB 4420 和替尼拉平的正式合成展示了其实用性。
• [EN] 2-AMINO-N-(AMINO-OXO-ARYL-LAMBDA6-SULFANYLIDENE)ACETAMIDE COMPOUNDS AND THEIR THERAPEUTIC USE<br/>[FR] COMPOSÉS DE 2-AMINO-N-(AMINO-OXO-ARYL-LAMBDA6-SULFANYLIDÈNE)ACÉTAMIDE ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：OXFORD DRUG DESIGN LTD

  公开号：WO2021123237A1

  公开（公告）日：2021-06-24

  The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain 2-amino-N-(amino-oxo-aryl-λ6- sulfanylidene)acetamide compounds (referred to herein as ANASIA compounds) that, inter alia, inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase (aaRS) (e.g., bacterial leucyl-tRNA synthetase, LeuRS). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase; to treat disorders that are ameliorated by the inhibition (e.g., selective inhibition) of bacterial aminoacyl-tRNA synthetase; to treat bacterial infections; etc.

  本发明一般涉及治疗化合物领域。更具体地，本发明涉及某些2-氨基-N-(氨基氧代芳基-λ6-砜基)乙酰胺化合物（以下简称为ANASIA化合物），该化合物在一些情况下抑制（例如，选择性抑制）细菌氨酰-tRNA合成酶（aaRS）（例如，细菌亮氨酰-tRNA合成酶，LeuRS）。本发明还涉及包含这种化合物的药物组合物，以及在体内外使用这种化合物和组合物来抑制（例如，选择性抑制）细菌氨酰-tRNA合成酶；治疗通过抑制（例如，选择性抑制）细菌氨酰-tRNA合成酶而得到改善的疾病；治疗细菌感染等。
• Regio-isomeric effects in tandem mass spectra of sulfonium cations generated from thiacyclane based sulfonium salts under soft ionization conditions
  作者：Vladimir G Zaikin、Anton V Kozlov、Roman S Borisov、Igor Yu Shchapin

  DOI：10.1177/1469066717723909

  日期：2018.2

  corresponding sulfonium salts. The latter salts readily gave off corresponding sulfonium cations under abovementioned desorption/ionization conditions and these cations were precursor ions in collision-induced dissociation experiments. The main quantitative and frequently qualitative differences between collision-induced dissociation spectra of isomers were manifested in mass numbers and relative intensities

  研究了偶电子锍离子的区域异构对串联电喷雾和基质辅助激光解吸/电离质谱的影响，该质谱是使用碰撞诱导解离记录的。最初的有机硫化物属于异构硫杂环烷系列（取代的 7- 和 8- 硫双环 [4.3.0] 壬烷，2- 和 3- 硫双环 [4.4.0] 癸烷）和苯基硫杂环戊烷。为了通过上述质谱法进行研究，将硫化物用甲基碘、乙基碘、它们的氘代类似物和三氟硼酸盐进行初步 S-烷基化，以形成相应的锍盐。后一种盐在上述解吸/电离条件下很容易释放出相应的锍阳离子，这些阳离子是碰撞诱导解离实验中的前体离子。异构体碰撞诱导解离光谱之间的主要定量和经常定性差异表现在离子的质量数和相对强度上，Alk-S+ = CHR（形式结构），源自含硫环的破坏。阳离子 Alk-S+ = CH2 的相应峰特别丰富，并且它们的强度通常大于其他 C 取代的同系物。2- 和 3- 苯基硫鎓阳离子的断裂特征之间的定性差异是只有后者才能消除中性 C2H4S
• Jur'ew; Lukina, Zhurnal Obshchei Khimii, 1954, vol. 24, p. 1449; engl. Ausg. S. 1433
  作者：Jur'ew、Lukina

  DOI：——

  日期：——
• Activity of Sulfonium Bisphosphonates on Tumor Cell Lines
  作者：Yonghui Zhang、Michael P. Hudock、Kilannin Krysiak、Rong Cao、Kyle Bergan、Fenglin Yin、Annette Leon、Eric Oldfield

  DOI：10.1021/jm700991k

  日期：2007.11.1

  We investigated three series of sulfonium bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines. The first series consisted of 6 cyclic sulfonium bisphosphonates, the most active species having an (average) IC50 of 89,mu M. The second consisted of 10 phenylalkyl and phenylalkoxy bisphosphonates, the most active species having an IC50 of 18,mu M. The third series consisted of 17 n-alkyl sulfonium bisphosphonates, the most active species having an IC50 of similar to 240 nM. Three QSAR models showed that the experimental cell growth inhibition results could be well predicted. We also determined the structures of one sulfonium bisphosphonate bound to farnesyl diphosphate synthase, finding that it binds exclusively to the dimethylallyl diphosphate binding site. These results are of interest since they show that sulfonium bisphosphonates can have potent activity against a variety of tumor cell lines, the most active species having IC50 values much lower than conventional nitrogen-containing bisphosphonates.