2-(4-methylthiophen-5-yl)ethanol | 159144-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(4-methylthiophen-5-yl)ethanol
• 英文别名: 2-(3-methylthiophen-2-yl)ethanol
• CAS: 159144-69-1
• 化学式: C₇H₁₀OS
• 分子量: 142.222
• InChiKey: XUDJPAANMBCCAC-UHFFFAOYSA-N

物化性质

• 沸点：
  232.3±25.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-methylthiophen-5-yl)ethanol 在 氯化亚砜 、 三氧化硫 、 氨 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-{[6-Amino-5-fluoro-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}-5-(2-hydroxyethyl)-4-methylthiophene-2-sulfonamide
  参考文献：
  名称：

  Orally active aminopyridines as inhibitors of tetrameric fructose-1,6-bisphosphatase

  摘要：

  A novel sulfonylureido pyridine series exemplified by compound 19 yielded potent inhibitors of FBPase showing significant glucose reduction and modest glycogen lowering in the acute db/db mouse model for Type-2 diabetes. Our inhibitors occupy the allosteric binding site and also extend into the dyad interface region of tetrameric FBPase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.044
• 作为产物：
  描述：

  2-(4-bromo-3-methylthiophen-2-yl)ethan-1-ol 在 正丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-(4-methylthiophen-5-yl)ethanol
  参考文献：
  名称：

  A protecting group-free synthesis of deazathiamine: A step toward inhibitor design

  摘要：

  The discovery of 3-deazathiamine diphosphate (deazaThDP) as a potent inhibitor analog of the cofactor thiamine diphosphate (ThDP) has highlighted the need for an efficient and scalable synthesis of deazaThDP. Such a method would facilitate development of analogs with the ability to inhibit individual ThDP-dependent enzymes selectively. Toward the goal of developing selective inhibitors of the mycobacterial enzyme 2-hydroxy-3-oxoadipate synthase (HOAS), we report an improved synthesis of deazaThDP without use of protecting groups. Tribromo-3-methylthiophene served as a versatile starting material whose selective functionalization permitted access to deazaThDP in five steps, with potential to make other analogs accessible in substantial amounts. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.053

文献信息

• Synthesis of 3-(Alkylamino)-, 3-(Alkoxy)-, 3-(Aryloxy)-, 3-(Alkylthio)-, and 3-(Arylthio)-1,2,4-triazines by Using a Unified Route with 3-(Methylsulfonyl)-1,2,4-triazine
  作者：Da-Hua Shi、Jitendra R. Harjani、Robert W. Gable、Jonathan B. Baell

  DOI：10.1002/ejoc.201600267

  日期：2016.6

  3-(methylsulfonyl)-1,2,4 triazine was also optimized. The reactivity of 3-(methylsulfonyl)-1,2,4-triazine towards alkyl and aryl thiols, primary and secondary alkylamines, phenols, and alcohols was explored, and the reactions were optimized to maximize the isolation of the corresponding 3-substituted 1,2,4-triazine. Good yields were obtained for the products of the reactions with all of the aforementioned nucleophiles

  在我们尝试合成 3-(烷硫基)-和 3-(烷氧基)-1,2,4-三嗪时，在 5-或 6-位没有取代基，合成它们预期的前体 3-(甲基磺酰基)-1， 2,4 三嗪也进行了优化。探索了 3-(甲基磺酰基)-1,2,4-三嗪对烷基和芳基硫醇、伯和仲烷基胺、酚和醇的反应性，并对反应进行了优化，以最大限度地分离相应的 3-取代 1 ,2,4-三嗪。通过使用碱金属碳酸盐，与除醇之外的所有上述亲核试剂的反应产物获得了良好的产率。通过使用合适的醇镁作为亲核试剂获得更高产率的 3-(烷氧基)-1,2,4-三嗪。
• Orally active aminopyridines as inhibitors of tetrameric fructose-1,6-bisphosphatase
  作者：Paul Hebeisen、Wolfgang Haap、Bernd Kuhn、Peter Mohr、Hans Peter Wessel、Ulrich Zutter、Stephan Kirchner、Armin Ruf、Jörg Benz、Catherine Joseph、Rubén Alvarez-Sánchez、Marcel Gubler、Brigitte Schott、Agnes Benardeau、Effie Tozzo、Eric Kitas

  DOI：10.1016/j.bmcl.2011.04.044

  日期：2011.6

  A novel sulfonylureido pyridine series exemplified by compound 19 yielded potent inhibitors of FBPase showing significant glucose reduction and modest glycogen lowering in the acute db/db mouse model for Type-2 diabetes. Our inhibitors occupy the allosteric binding site and also extend into the dyad interface region of tetrameric FBPase. (C) 2011 Elsevier Ltd. All rights reserved.
• A protecting group-free synthesis of deazathiamine: A step toward inhibitor design
  作者：Hong Zhao、Luiz Pedro S. de Carvalho、Carl Nathan、Ouathek Ouerfelli

  DOI：10.1016/j.bmcl.2010.09.053

  日期：2010.11

  The discovery of 3-deazathiamine diphosphate (deazaThDP) as a potent inhibitor analog of the cofactor thiamine diphosphate (ThDP) has highlighted the need for an efficient and scalable synthesis of deazaThDP. Such a method would facilitate development of analogs with the ability to inhibit individual ThDP-dependent enzymes selectively. Toward the goal of developing selective inhibitors of the mycobacterial enzyme 2-hydroxy-3-oxoadipate synthase (HOAS), we report an improved synthesis of deazaThDP without use of protecting groups. Tribromo-3-methylthiophene served as a versatile starting material whose selective functionalization permitted access to deazaThDP in five steps, with potential to make other analogs accessible in substantial amounts. (C) 2010 Elsevier Ltd. All rights reserved.