Methyl (Z,E)-6-methyl-3,5-heptadienonate | 60421-81-0

• 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 (Z,E)-6-methyl-3,5-heptadienonate
• 英文别名: Methyl 6-methylhepta-3,5-dienoate；methyl 6-methylhepta-3,5-dienoate
• CAS: 60421-81-0
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: WGXNFBXADCTXPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl (Z,E)-6-methyl-3,5-heptadienonate
  参考文献：
  名称：

  Lithium 3-Lithio-3-tosylalkanoates: .beta.-Acylvinyl Anion Equivalents of .beta.-Lithiated .alpha.,.beta.-Unsaturated Carboxylic Acids

  摘要：

  The dilithiation of beta-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 degrees C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11. They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12. When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoracetic anhydride and base-promoted elimination alpha,beta-butenolides are obtained. This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci). The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afford alpha,beta- and/or beta,gamma-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively. The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).

  DOI：

  10.1021/jo00090a043