2-mercapto-5-methoxy-5-oxopentanoic acid | 1072103-52-6

• 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: 2-mercapto-5-methoxy-5-oxopentanoic acid
• CAS: 1072103-52-6
• 化学式: C₆H₁₀O₄S
• 分子量: 178.209
• InChiKey: MJXVJOIPYGBDPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-methyl-2-phenyl-1,3-oxathiolan-5-one 、 丙烯酸甲酯（MA） 在 cerium(III) chloride 、 sodium iodide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 以85%的产率得到2-mercapto-5-methoxy-5-oxopentanoic acid
  参考文献：
  名称：

  Direct introduction of glycine/mercaptoacetic acid units into electron-poor alkenes: a novel route to functionally rich α-amino/α-mercapto acids

  摘要：

  The first example of an operationally simple direct introduction of glycine/mercaptoacetic acid units into electron-poor alkenes is reported. In this protocol, Lewis acid-catalyzed Michael addition of activated glycine or mercaptoacetic acid, that is 2-phenyl-1,3-oxazol-5-one or 2-methyl-2-phenyl-1,3-oxathiolan-5-one, to various electron-poor alkenes in water/1,4-dioxane (1:2, v/v) solvent system diastereoselectively affords the corresponding functionally rich alpha-amino acids or alpha-mercapto acids, respectively, in high yields at ambient temperature. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.103

文献信息

• Direct introduction of glycine/mercaptoacetic acid units into electron-poor alkenes: a novel route to functionally rich α-amino/α-mercapto acids
  作者：Lal Dhar S. Yadav、Ankita Rai

  DOI：10.1016/j.tetlet.2008.07.103

  日期：2008.9

  The first example of an operationally simple direct introduction of glycine/mercaptoacetic acid units into electron-poor alkenes is reported. In this protocol, Lewis acid-catalyzed Michael addition of activated glycine or mercaptoacetic acid, that is 2-phenyl-1,3-oxazol-5-one or 2-methyl-2-phenyl-1,3-oxathiolan-5-one, to various electron-poor alkenes in water/1,4-dioxane (1:2, v/v) solvent system diastereoselectively affords the corresponding functionally rich alpha-amino acids or alpha-mercapto acids, respectively, in high yields at ambient temperature. (C) 2008 Elsevier Ltd. All rights reserved.