(+/-)-6,7-dihydro-5-oxo-LTB4 methyl ester | 141201-04-9

• 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: (+/-)-6,7-dihydro-5-oxo-LTB4 methyl ester
• 英文别名: methyl (8E,10E,14Z)-12-hydroxy-5-oxoicosa-8,10,14-trienoate
• CAS: 141201-04-9
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: GTZURRIPACMMIK-AAASEFCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 ammonium cerium(IV) nitrate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以69%的产率得到(+/-)-6,7-dihydro-5-oxo-LTB4 methyl ester
  参考文献：
  名称：

  Conjugate reduction vicinal to butadiene tricarbonyl iron complexes. Application to the synthesis of (.+-.)-6,7-dihydro-LTB4 methyl ester

  摘要：

  The conjugate reduction of enones vicinal to butadiene tricarbonyl iron complexes was best performed using Red-Al/CuBr/2-butanol in THF. This reaction was applied to alpha,beta-unsaturated ketone 13 for the synthesis of three possible metabolites of LTB4 (as their methyl esters 4a, 4b, 4c) generated via a 6,7-reductase pathway. Ketone 13 was synthesized in five steps starting from the organometallic complex 5. Conjugate reduction of 13 selectively saturated the 6,7 double bond to give ketone 14. Potassium borohydride reduction of 16 yielded a mixture of diols 17 which upon decomplexation using CAN afforded (+/-)-6,7-dihydro-LTB4 methyl ester 4a along with its 5-epimer 4b. The 5-keto derivative 4c was also prepared by direct decomplexation of 16.

  DOI：

  10.1021/jo00038a026