15-bromo-16-hydroxy-α-linolenic acid methyl ester | 271780-31-5

• 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: 15-bromo-16-hydroxy-α-linolenic acid methyl ester
• CAS: 271780-31-5
• 化学式: C₁₉H₃₃BrO₃
• 分子量: 389.373
• InChiKey: YSHDRAKFJMTTNW-DPTWWRMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  23.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  15-bromo-16-hydroxy-α-linolenic acid methyl ester 在 4-二甲氨基吡啶 、 1,4,8,11-四硫杂环十四烷 、 Lipase PS 、 4 A molecular sieve 、 N,N'-二环己基碳二亚胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 66.0h， 生成 (9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester
  参考文献：
  名称：

  Preparation of Optically Active 15-Epoxy-a-linolenic Acids and Their Anti-Rice Blast Fungus Activities

  摘要：

  By the action of NBS in aq. DME, alpha-linolenic acid was oxidized to 15-bromo-16-hydroxy-alpha-linolenic acid in 35% conversion yield. The bromohydrin was treated with lipase-PS and vinyl acetate to give the resolved acetate and bromohydrin. (15S,16R)- and (15R,16S)-Epoxy-alpha-linolenic acids were prepared from the corresponding resolved products. A comparison of anti-rice blast fungus activities showed that an unnatural epoxide is stronger than the natural epoxide.

  DOI：

  10.3987/com-99-s147
• 作为产物：
  描述：

  亚麻酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙二醇二甲醚 为溶剂， 以35%的产率得到15-bromo-16-hydroxy-α-linolenic acid methyl ester
  参考文献：
  名称：

  Preparation of Optically Active 15-Epoxy-a-linolenic Acids and Their Anti-Rice Blast Fungus Activities

  摘要：

  By the action of NBS in aq. DME, alpha-linolenic acid was oxidized to 15-bromo-16-hydroxy-alpha-linolenic acid in 35% conversion yield. The bromohydrin was treated with lipase-PS and vinyl acetate to give the resolved acetate and bromohydrin. (15S,16R)- and (15R,16S)-Epoxy-alpha-linolenic acids were prepared from the corresponding resolved products. A comparison of anti-rice blast fungus activities showed that an unnatural epoxide is stronger than the natural epoxide.

  DOI：

  10.3987/com-99-s147

文献信息

• Preparation of the enantiomers of hydroxy-C18 fatty acids and their anti-rice blast fungus activities
  作者：Tadahiro Kato、Toshio Nakai、Rumiko Ishikawa、Aya Karasawa、Tsuneo Namai

  DOI：10.1016/s0957-4166(01)00486-4

  日期：2001.10

  the infected rice plants as an enantiomeric mixture with <10% e.e., a procedure for the chemical preparation of both enantiomers was explored, starting from the original fatty acids 4 and 5. The anti-rice blast fungus activities of both enantiomers of the allylic alcohols 1–3 and epoxy α-linolenic acids 12 and 13 demonstrate no noticeable correlation between the activity and chirality.

  为了检查抗稻瘟病菌的活性和烯丙基醇的手性之间的相关性1 - 3，这是从受感染的水稻植物，其特征为具有<10％ee的，对于两者的化学制备过程对映体混合物从原始脂肪酸4和5开始探索对映体。烯丙基醇的两种对映体的抗稻瘟病菌的活动13和环氧树脂α-亚麻酸12和13表现出的活性和手性之间没有明显的相关性。