methyl 5-[(2S,5R)-5-[(1R)-1-(2-bromoacetyl)oxynonyl]oxolan-2-yl]pentanoate | 765300-43-4

• 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 5-[(2S,5R)-5-[(1R)-1-(2-bromoacetyl)oxynonyl]oxolan-2-yl]pentanoate
• CAS: 765300-43-4
• 化学式: C₂₁H₃₇BrO₅
• 分子量: 449.426
• InChiKey: CJDWDCLHSGIKSO-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-[(2S,5R)-5-[(1R)-1-(2-bromoacetyl)oxynonyl]oxolan-2-yl]pentanoate 、 1,3-丙二胺 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以84%的产率得到methyl 5-[(2S,5R)-5-[(1R)-1-[2-(3-aminopropylamino)acetyl]oxynonyl]oxolan-2-yl]pentanoate
  参考文献：
  名称：

  Absolute Configuration of a Hydroxyfuranoid Acid from the Pelage of the Genus Bos, 18-(6S,9R,10R)-Bovidic Acid

  摘要：

  Pelage extracts of the banteng (Bos javanicus), the domestic cattle (B. taurus), the gaur (B. frontalis), and the yak (B. grunniens) were investigated by FABMS and NMR. An 18-carbon hydroxyfuranoid acid, 1 (10-hydroxy-6,9-oxidooctadecanoic acid), first reported from the wool of the domestic sheep (Ovis aries) was confirmed in B. frontalis; we suspend judgment on the occurrence of this compound in the other species we examined. The stereochemistry of 1, determined by Mosher NMR and CD tweezer methods, was assigned as 6S, 9R, 10R. We propose the name bovidic acid for this and homologous alpha-hydroxylated 2,5-tetrahydrofuranoid carboxylic acids, in reference to the family Bovidae, which represents their sole known natural source.

  DOI：

  10.1021/np049937u
• 作为产物：
  描述：

  5-{(2S,5R)-2,3,4,5-tetrahydro-5-[(1R)-1-hydroxynonyl]furan-2-yl}pentanoic acid 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 methyl 5-[(2S,5R)-5-[(1R)-1-(2-bromoacetyl)oxynonyl]oxolan-2-yl]pentanoate
  参考文献：
  名称：

  Absolute Configuration of a Hydroxyfuranoid Acid from the Pelage of the Genus Bos, 18-(6S,9R,10R)-Bovidic Acid

  摘要：

  Pelage extracts of the banteng (Bos javanicus), the domestic cattle (B. taurus), the gaur (B. frontalis), and the yak (B. grunniens) were investigated by FABMS and NMR. An 18-carbon hydroxyfuranoid acid, 1 (10-hydroxy-6,9-oxidooctadecanoic acid), first reported from the wool of the domestic sheep (Ovis aries) was confirmed in B. frontalis; we suspend judgment on the occurrence of this compound in the other species we examined. The stereochemistry of 1, determined by Mosher NMR and CD tweezer methods, was assigned as 6S, 9R, 10R. We propose the name bovidic acid for this and homologous alpha-hydroxylated 2,5-tetrahydrofuranoid carboxylic acids, in reference to the family Bovidae, which represents their sole known natural source.

  DOI：

  10.1021/np049937u