5-ethoxy-4-(6-methoxycarbonylhexyl)-2,3-dihydrofuran-3-one | 662152-07-0

• 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: 5-ethoxy-4-(6-methoxycarbonylhexyl)-2,3-dihydrofuran-3-one
• 英文别名: 5-Ethoxy-4-(6-methoxycarbonylhexyl)-2,3-di-hydrofuran-3-one；methyl 7-(2-ethoxy-4-oxofuran-3-yl)heptanoate
• CAS: 662152-07-0
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: XGTSUGTWMARYOO-UHFFFAOYSA-N

物化性质

• 沸点：
  379.7±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  5-ethoxy-4-(6-methoxycarbonylhexyl)-2,3-dihydrofuran-3-one 在 二异丁基氢化铝 、 水 作用下， 以 乙醚 、 正己烷 为溶剂， 以12%的产率得到2,5-dihydro-2-oxo-3-furanheptanoate
  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 三乙基硅烷 、 4-二甲氨基吡啶 、 lithium perchlorate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 三氟乙酸 为溶剂， 反应 15.0h， 生成 5-ethoxy-4-(6-methoxycarbonylhexyl)-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

文献信息

• Heterocyclic analogs of prostaglandins: III. Synthesis of 10-oxa-13-aza, 11-oxa-13-aza, and 9-oxa-7-aza prostanoids from 3-acyl-and 3-(3-arylprop-2-enoyl)furan-2,4-diones
  作者：F. S. Pashkovskii、E. M. Shchukina、M. G. Gribovskii、F. A. Lakhvich

  DOI：10.1134/s1070428006040087

  日期：2006.4

  A number of new 10-oxa-13-aza, 11-oxa-13-aza, and 9-oxa-7-aza prostanoids belonging to the B series were synthesized on the basis of 3-acyl- and 3-(3-arylprop-2-enoyl)furan-2,4(3H,5H)-diones. The scheme of synthesis includes selective hydrogenation of the exocyclic carbonyl group and reduction of the conjugated double bond in the acyl fragment of 3-acyl- and 3-(3-arylprop-2-enoyl)furan-2,4(3H, 5H)-diones to obtain 3-alkyl- and 3-(3-arylpropyl)furan-2,4(3H,5H)-diones, transformation of the latter into the corresponding regioisomeric enol ethers via regioselective O-alkylation, and treatment of the enol ethers with primary aliphatic amines.