methyl-2-dodecyl-2-oxiranepentanoate | 149070-34-8

• 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-2-dodecyl-2-oxiranepentanoate
• 英文别名: Methyl 5-(2-dodecyloxiran-2-yl)pentanoate
• CAS: 149070-34-8
• 化学式: C₂₀H₃₈O₃
• 分子量: 326.52
• InChiKey: YVRJJWBDAGDJEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-巯基丙酸甲酯 、 methyl-2-dodecyl-2-oxiranepentanoate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 10.5h， 以86%的产率得到methyl-<6-hydroxy-6-<(2-methoxycarbonylethyl)-thio>methyl>-octadecanoate
  参考文献：
  名称：

  Synthesis and biological properties of hydroxythioether fatty acids related to leukotrienes: Antagonists and agonists of slow-reacting substance of anaphylaxis (SRS-A)

  摘要：

  A series of 6-hydroxy-7-thioether and 6-thioether-7-hydroxy derivatives of commercially available petroselinic acid and 5-hydroxy-6-thioether derivatives of fatty acids containing an aromatic moiety were synthesized. Several of the compounds have exhibited SRS-A antagonist (eg, 5, 10)/agonist (eg, 34, 35) activity. Compound 5 antagonized SRS-A-induced contractions of the isolated guinea pig ileum with IC50 = 0.09 muM.

  DOI：

  10.1016/0223-5234(93)90073-n
• 作为产物：
  描述：

  methyl 6-oxooctadecanoate 在 3-tert-butyl-4-hydroxy-5-methylbenzenethiol 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 methyl-2-dodecyl-2-oxiranepentanoate
  参考文献：
  名称：

  Synthesis and biological properties of hydroxythioether fatty acids related to leukotrienes: Antagonists and agonists of slow-reacting substance of anaphylaxis (SRS-A)

  摘要：

  A series of 6-hydroxy-7-thioether and 6-thioether-7-hydroxy derivatives of commercially available petroselinic acid and 5-hydroxy-6-thioether derivatives of fatty acids containing an aromatic moiety were synthesized. Several of the compounds have exhibited SRS-A antagonist (eg, 5, 10)/agonist (eg, 34, 35) activity. Compound 5 antagonized SRS-A-induced contractions of the isolated guinea pig ileum with IC50 = 0.09 muM.

  DOI：

  10.1016/0223-5234(93)90073-n

文献信息

• Synthesis and biological properties of hydroxythioether fatty acids related to leukotrienes: Antagonists and agonists of slow-reacting substance of anaphylaxis (SRS-A)
  作者：W Ho、WE Hageman、KG Stanley、WR Gallant、DA Cherry、RJ Mohrbacher、BE Maryanoff、AB Reitz、BA Duhl-Emswiler

  DOI：10.1016/0223-5234(93)90073-n

  日期：1993.1

  A series of 6-hydroxy-7-thioether and 6-thioether-7-hydroxy derivatives of commercially available petroselinic acid and 5-hydroxy-6-thioether derivatives of fatty acids containing an aromatic moiety were synthesized. Several of the compounds have exhibited SRS-A antagonist (eg, 5, 10)/agonist (eg, 34, 35) activity. Compound 5 antagonized SRS-A-induced contractions of the isolated guinea pig ileum with IC50 = 0.09 muM.