7-(2-甲基-5-氧代-2H-呋喃-4-基)庚酸甲酯 | 352007-97-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 7-(2-甲基-5-氧代-2H-呋喃-4-基)庚酸甲酯
• 英文名称: 3-(6-carbomethoxyhexyl)-5-methylfuran-2(5H)-one
• 英文别名: 3-Furanheptanoic acid, 2,5-dihydro-5-methyl-2-oxo-, methyl ester；methyl 7-(2-methyl-5-oxo-2H-furan-4-yl)heptanoate
• CAS: 352007-97-7
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: RYWKKKWQEVCLSI-UHFFFAOYSA-N

物化性质

• 沸点：
  364.7±25.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(2-甲基-5-氧代-2H-呋喃-4-基)庚酸甲酯 在 1,1,2,3-四甲基胍 异氰酸苯酯 、 三乙胺 作用下， 以 苯 为溶剂， 生成 methyl 7-{5-methyl-2-oxo-4-[5-(pyridin-4-yl)-4,5-dihydroisoxazol-3-yl]tetrahydrofuran-3-yl}heptanoate
  参考文献：
  名称：

  前列腺素的杂环类似物：II。α-和ω-链上的异恶唑和异恶唑啉片段合成10-氧杂前列腺素

  摘要：

  By the use of "nitrile oxide procedure" from 3-aIkyl(arylalkyl)-substituted 2,5-dihydro-2-furanones new 10-oxaprostanoids were prepared containing an isoxazole (isoxazoline) fragment in the alpha- or omega-prostanoid chain.

  DOI：

  10.1134/s1070428002120126
• 作为产物：
  描述：

  7-甲氧基-7-氧代庚酸 在 盐酸 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 silica gel 、 sodium cyanoborohydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 丙酮 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 溶剂黄146 、 甲苯 为溶剂， 反应 23.0h， 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

文献信息

• ——
  作者：F. S. Pashkovsky、Ya. M. Katok、E. V. Koroleva、F. A. Lakhvich

  DOI：10.1023/a:1017535904788

  日期：——
• Heterocyclic analogs of prostaglandins: II. Synthesis of 10-oxaprostanoids with isoxazole and isoxazoline fragments in α-and ω-chain
  作者：F. S. Pashkovskii、Ya. M. Katok、E. M. Shchukina、E. V. Koroleva、F. A. Lakhvich

  DOI：10.1134/s1070428002120126

  日期：2006.2

  By the use of "nitrile oxide procedure" from 3-aIkyl(arylalkyl)-substituted 2,5-dihydro-2-furanones new 10-oxaprostanoids were prepared containing an isoxazole (isoxazoline) fragment in the alpha- or omega-prostanoid chain.
• Heterocyclic Analogs of Prostaglandins: I. Synthesis of 3-Alkyl(Aralkyl)-2,5-dihydrofuran-2-ones as Synthons for 11-Deoxy-10-oxaprostanoids
  作者：F. S. Pashkovskii、Ya. M. Katok、T. S. Khlebnikova、E. V. Koroleva、F. A. Lakhvich

  DOI：10.1023/b:rujo.0000003193.75790.de

  日期：2003.7

  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.