5-Methyl-3-octanoyl-furan-2,4-dione | 662152-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Methyl-3-octanoyl-furan-2,4-dione
• CAS: 662152-03-6
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: VGMHSVYYBJWREM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Methyl-3-octanoyl-furan-2,4-dione 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 5-ethoxy-2-methyl-4-octyl-2,3-dihydrofuran-3-one
  参考文献：
  名称：

  Heterocyclic Analogs of Prostaglandins: I. Synthesis of 3-Alkyl(Aralkyl)-2,5-dihydrofuran-2-ones as Synthons for 11-Deoxy-10-oxaprostanoids

  摘要：

  3-Acyl(arylmethyleneacyl)tetronic acids were synthesized. Selective hydrogenation of the carbonyl group in the acyl fragment and reduction of the conjugated double bond afforded in high yield the corresponding 3-alkyl(aralkyl) derivatives possessing either natural or modified prostaglandin alpha-chain. Reduction of the conjugated double bond in vinylogous 3-alkyl(aralkyl)tetronic acid amides with sodium cyanotrihydridoborate gave a mixture of stereoisomeric beta-amino lactones which underwent retro-Michael elimination of the amine residue, leading to 3-alkyl(aralkyl)-2,5-dihydrofuran-2-ones. The latter can be regarded as synthons for 11-deoxy-10-oxaprostanoids.

  DOI：

  10.1023/b:rujo.0000003193.75790.de
• 作为产物：
  描述：

  1-ethoxycarbonylethyl 3-oxodecanoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到5-Methyl-3-octanoyl-furan-2,4-dione
  参考文献：
  名称：

  Heterocyclic Analogs of Prostaglandins: I. Synthesis of 3-Alkyl(Aralkyl)-2,5-dihydrofuran-2-ones as Synthons for 11-Deoxy-10-oxaprostanoids

  摘要：

  3-Acyl(arylmethyleneacyl)tetronic acids were synthesized. Selective hydrogenation of the carbonyl group in the acyl fragment and reduction of the conjugated double bond afforded in high yield the corresponding 3-alkyl(aralkyl) derivatives possessing either natural or modified prostaglandin alpha-chain. Reduction of the conjugated double bond in vinylogous 3-alkyl(aralkyl)tetronic acid amides with sodium cyanotrihydridoborate gave a mixture of stereoisomeric beta-amino lactones which underwent retro-Michael elimination of the amine residue, leading to 3-alkyl(aralkyl)-2,5-dihydrofuran-2-ones. The latter can be regarded as synthons for 11-deoxy-10-oxaprostanoids.

  DOI：

  10.1023/b:rujo.0000003193.75790.de