2,2-dimethyl-6-(5-methoxycarbonylpentyl)-4H-1,3-dioxin-4-one | 662152-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-6-(5-methoxycarbonylpentyl)-4H-1,3-dioxin-4-one
• 英文别名: methyl 6-(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)hexanoate
• CAS: 662152-00-3
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: BVVRIDYGYVIXFH-UHFFFAOYSA-N

物化性质

• 沸点：
  361.7±42.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-6-(5-methoxycarbonylpentyl)-4H-1,3-dioxin-4-one 在 盐酸 、 四丁基氟化铵 、 silica gel 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 甲苯 为溶剂， 反应 6.5h， 生成 7-(2-甲基-5-氧代-2H-呋喃-4-基)庚酸甲酯
  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 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 丙酮 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 16.5h， 生成 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