methyl 7-(6,6-dimethyl-2,4-dioxotetrahydro-2H-pyran-3-yl)-7-oxoheptanoate | 662151-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: methyl 7-(6,6-dimethyl-2,4-dioxotetrahydro-2H-pyran-3-yl)-7-oxoheptanoate
• CAS: 662151-98-6
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: NTFPYVQJPUZWNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 7-(6,6-dimethyl-2,4-dioxotetrahydro-2H-pyran-3-yl)-7-oxoheptanoate 在 丙酮 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以67%的产率得到2,2-dimethyl-6-(5-methoxycarbonylpentyl)-4H-1,3-dioxin-4-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：

  7-甲氧基-7-氧代庚酸 、 6,6-dimethyldihydro-2H-pyran-2,4(3H)-dione 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 15.0h， 生成 methyl 7-(6,6-dimethyl-2,4-dioxotetrahydro-2H-pyran-3-yl)-7-oxoheptanoate
  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