3-(6-ethoxycarbonylhexyl)tetrahydrofuran-2,4-dione | 367909-50-0

• 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: 3-(6-ethoxycarbonylhexyl)tetrahydrofuran-2,4-dione
• 英文别名: ethyl 7-(2,4-dioxotetrahydrofuran-3-yl)heptanoate；3-(6-Ethoxycarbonyl)tetronic acid；ethyl 7-(2,4-dioxooxolan-3-yl)heptanoate
• CAS: 367909-50-0
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: ZNHDYCLAXDQBFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(6-ethoxycarbonylhexyl)tetrahydrofuran-2,4-dione 以 二氯甲烷 为溶剂， 生成 ethyl 7-(2-heptylamino-4-oxo-4,5-dihydrofuran-3-yl)heptanoate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1134/s1070428006040087
• 作为产物：
  描述：

  庚二酸氢乙酯 在 三乙基硅烷 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 三氟乙酸 为溶剂， 生成 3-(6-ethoxycarbonylhexyl)tetrahydrofuran-2,4-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1134/s1070428006040087

文献信息

• An Efficient Synthesis of Alkyl Substituted Cyclic 1,3-Diones
  作者：Felix S. Pashkovsky、Igor P. Lokot、Fedor A. Lakhvich

  DOI：10.1055/s-2001-16787

  日期：——

  An efficient method for the synthesis of cyclic α-alkyl β-dicarbonyl compounds of cyclopentane, cyclohexane, tetronic acid and α-pyrone series is described. The method consists of the selective transformation of the corresponding cyclic β,β′-tricarbonyl compounds by NaBH3CN in a mixture of THF and 2N aqueous HCl.

  描述了一种合成环状α-烷基β-二酮化合物（包括环戊烷、环己烷、四氢呋喃酸和α-吡喃）高效的方法。该方法包括在THF和2N盐酸水溶液混合物中，利用NaBH3CN选择性转化相应的环状β,β′-三酮化合物。
• ——
  作者：F. S. Pashkovsky、I. P. Lokot"、F. A. Lakhvich

  DOI：10.1023/a:1009511208712

  日期：——

  Efficient synthesis of cyclic alpha-alkyl-beta-dicarbonyl compounds of the cyclopentane, cyclohexane, tetronic acid, and alpha-pyrone series from the corresponding cyclic alpha-acyl-beta-dicarbonyl compounds under the action of NaBH3(CN) in a THF-HCl system is described.
• 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.