7-(2,4-Dioxo-tetrahydro-furan-3-yl)-7-oxo-heptanoic acid methyl ester | 375374-83-7

• 分子结构分类: 有机化合物
• 英文名称: 7-(2,4-Dioxo-tetrahydro-furan-3-yl)-7-oxo-heptanoic acid methyl ester
• CAS: 375374-83-7
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: RGWZKYVZNAQJRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  7-(2,4-Dioxo-tetrahydro-furan-3-yl)-7-oxo-heptanoic acid methyl ester 在 三乙基硅烷 、 lithium perchlorate 作用下， 以 三氟乙酸 为溶剂， 以88%的产率得到3-Carboxyhexyltetronic acid methyl ester
  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：

  4-羟乙酰乙酸内酯 、 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 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以87%的产率得到7-(2,4-Dioxo-tetrahydro-furan-3-yl)-7-oxo-heptanoic acid methyl ester
  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

• 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。