5-methyl-3-octyltetronic acid | 662152-06-9

• 分子结构分类: 有机化合物
• 英文名称: 5-methyl-3-octyltetronic acid
• CAS: 662152-06-9
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: JVQSHDQKZPNFMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-methyl-3-octyltetronic acid 在 四丁基氢氧化铵 作用下， 以 乙醇 为溶剂， 反应 25.0h， 生成 4-benzylamino-5-methyl-3-octylfuran-2(5H)-one
  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：

  5-Methyl-3-octanoyl-furan-2,4-dione 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到5-methyl-3-octyltetronic acid
  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