methyl (3S)-acetylsulfanylbutanoate | 142148-08-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (3S)-acetylsulfanylbutanoate
• 英文别名: Methyl 3(S)-(acetylthio)butanoate；methyl (3S)-3-acetylsulfanylbutanoate
• CAS: 142148-08-1
• 化学式: C₇H₁₂O₃S
• 分子量: 176.236
• InChiKey: JWJRIOOXTVVAGA-YFKPBYRVSA-N

物化性质

• 沸点：
  232.0±23.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3S)-acetylsulfanylbutanoate 在 甲醇 、 sodium methylate 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Alkylsulfanyl analogs as potent α 2 δ ligands

  摘要：

  We identified novel (3R, 5S)-3-aminomethyl-5-methanesulfanyl hexanoic acid (5a: DS75091588) and (3R, 5S)-3-aminomethyl-5-ethanesulfanyl hexanoic acid (6a: DS18430756) as sulfur-containing y-amino acid derivatives that were useful for the treatment of neuropathic pain. These two compounds exhibited a potent analgesic effect in animal models of both type I diabetes and type II diabetes, and good pharmacokinetics. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.05.006
• 作为产物：
  描述：

  (-)-(R)-Methyl 3-(mesyloxy)butanoate 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以8.1 g的产率得到methyl (3S)-acetylsulfanylbutanoate
  参考文献：
  名称：

  Alkylsulfanyl analogs as potent α 2 δ ligands

  摘要：

  We identified novel (3R, 5S)-3-aminomethyl-5-methanesulfanyl hexanoic acid (5a: DS75091588) and (3R, 5S)-3-aminomethyl-5-ethanesulfanyl hexanoic acid (6a: DS18430756) as sulfur-containing y-amino acid derivatives that were useful for the treatment of neuropathic pain. These two compounds exhibited a potent analgesic effect in animal models of both type I diabetes and type II diabetes, and good pharmacokinetics. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.05.006

文献信息

• Effect of the α-Methyl Substituent on Chemoselectivity in Esterase-Catalyzed Hydrolysis of <i>S</i>-Acetyl Sulfanylalkanoates
  作者：Ish Kumar、Ravinder S. Jolly

  DOI：10.1021/ol990544+

  日期：1999.7.1

  The isomeric compounds 1 and 3, which differ only in the position of a methyl substituent, give opposite chemoselectivities in an esterase-catalyzed hydrolysis reaction. The esterase was chemoselective for the oxoester in 1, but for the thiol ester group in 3. A high enantioselectivity was observed for both 1 and 3.

  仅在甲基取代基的位置上不同的异构体化合物1和3在酯酶催化的水解反应中具有相反的化学选择性。酯酶对1中的氧代酯具有化学选择性，但对3中的硫醇酯基具有化学选择性。对1和3均观察到高对映选择性。
• Fluorinated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：Merck Frosst Canada, Inc.

  公开号：US05270324A1

  公开（公告）日：1993-12-14

  Compounds having the formula I: ##STR1## are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.

  具有以下化学式的化合物 I: ##STR1## 是白三烯拮抗剂，也是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎症和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥反应。
• Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：Merck Frosst Canada, Inc.

  公开号：US05565473A1

  公开（公告）日：1996-10-15

  Compounds having the formula I: ##STR1## are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.

  具有以下化学式I的化合物是白三烯拮抗剂和白三烯生物合成抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥反应。
• Saturated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：Merck Frosst Canada, Inc.

  公开号：US05428033A1

  公开（公告）日：1995-06-27

  Compounds having the formula I: ##STR1## are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.

  化学式为I：##STR1##的化合物是白三烯拮抗剂和白三烯生物合成抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑血管痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和同种异体移植排斥反应。
• US5270324A
  申请人：——

  公开号：US5270324A

  公开（公告）日：1993-12-14