4-(methylsulfonyl)thiomorpholine | 98137-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: 4-(methylsulfonyl)thiomorpholine
• 英文别名: 4-methanesulfonyl-thiomorpholine；4-Methylsulfonyl-thiamorpholin；4-Methylsulfonylthiomorpholine
• CAS: 98137-57-6
• 化学式: C₅H₁₁NO₂S₂
• 分子量: 181.28
• InChiKey: UXYZUTMHAJRMKG-UHFFFAOYSA-N

物化性质

• 沸点：
  313.7±52.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氟苯甲酸甲酯 、 4-(methylsulfonyl)thiomorpholine 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到1-(4-fluorophenyl)-2-(thiomorpholinosulfonyl)ethan-1-one
  参考文献：
  名称：

  Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors

  摘要：

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.124
• 作为产物：
  描述：

  硫代吗啉 、 二甲基亚砜 在 potassium iodide 作用下， 反应 8.0h， 以91%的产率得到4-(methylsulfonyl)thiomorpholine
  参考文献：
  名称：

  Electrosynthesis of sulfonamides from DMSO and amines under mild conditions

  摘要：

  在室温下，以DMSO为溶剂，使用带有-SO₂Me基团的前体，开发了一种新的电化学氧化和胺化反应，用于合成磺酰胺。

  DOI：

  10.1039/d1cc00026h

文献信息

• Iodine-Catalyzed Oxidative Amination of Sodium Sulfinates: A Convenient Approach to the Synthesis of Sulfonamides under Mild Conditions
  作者：Chonchanok Buathongjan、Danupat Beukeaw、Sirilata Yotphan

  DOI：10.1002/ejoc.201403531

  日期：2015.3

  The iodine-catalyzed oxidative amination of sodium sulfinates in the presence of sodium percarbonate as the oxidant has been developed. The reaction shows good substrate scope and tolerates a wide range of functionalities in both amine and sodium sulfinate substrates. Aliphatic amines, heteroaromatic amines and hydrochloride salts of amines can be employed as the amine sources in this transformation

  在作为氧化剂的过碳酸钠存在下，碘催化亚磺酸钠的氧化胺化已被开发出来。该反应显示出良好的底物范围，并在胺和亚磺酸钠底物上耐受广泛的官能度。脂族胺、杂芳族胺和胺的盐酸盐可用作该转化中的胺源。机理研究表明，反应过程中可能涉及自由基途径。这种不含过渡金属的方案为在温和条件下以中等至良好的收率制备一系列磺胺类药物提供了一种替代且方便的方法。
• Synthesis of Potential Anticancer Agents. XXI. Nitrosated Sulfonamides Related to Myleran
  作者：THOMAS P. JOHNSTON、CONRAD L. KUSSNER、LEE B. HOLUM

  DOI：10.1021/jo01073a024

  日期：1960.3
• Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors
  作者：William K.C. Park、Robert M. Kennedy、Scott D. Larsen、Steve Miller、Bruce D. Roth、Yuntao Song、Bruce A. Steinbaugh、Kevin Sun、Bradley D. Tait、Mark C. Kowala、Bharat K. Trivedi、Bruce Auerbach、Valerie Askew、Lisa Dillon、Jeffrey C. Hanselman、Zhiwu Lin、Gina H. Lu、Andrew Robertson、Catherine Sekerke

  DOI：10.1016/j.bmcl.2007.11.124

  日期：2008.2

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.
• Electrosynthesis of sulfonamides from DMSO and amines under mild conditions
  作者：Zhiguan Lin、Liangbin Huang、Gaoqing Yuan

  DOI：10.1039/d1cc00026h

  日期：——

  With DMSO as the solvent and the precursor of a –SO₂Me unit at room temperature, a novel electrochemical oxidization and amination of DMSO with amines was developed for the synthesis of sulfonamides.

  在室温下，以DMSO为溶剂，使用带有-SO₂Me基团的前体，开发了一种新的电化学氧化和胺化反应，用于合成磺酰胺。