4-hydroxy-2-octyl-acetoacetic acid-lactone | 351499-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-hydroxy-2-octyl-acetoacetic acid-lactone
• 英文别名: 4-Hydroxy-2-octyl-acetessigsaeure-lacton；3-Octyloxolane-2,4-dione
• CAS: 351499-09-7
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: ZVCWIIMAGNIUMT-UHFFFAOYSA-N

物化性质

• 沸点：
  358.7±35.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-octyl-acetoacetic acid-lactone 以 二氯甲烷 为溶剂， 生成 5-cyclohexylamino-4-octylfuran-3(2H)-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：

  2-辛基乙酰乙酸乙酯 在 氯仿 、 溴 作用下， 生成 4-hydroxy-2-octyl-acetoacetic acid-lactone
  参考文献：
  名称：

  [四元酸衍生物。二。3-取代的反式酸[]。

  摘要：

  DOI：

  10.1002/ardp.19582910407

文献信息

• A new efficient synthesis of alkyl substituted Δ 2 -butenolides
  作者：Felix S Pashkovsky、Yadviga M Katok、Tatyana S Khlebnicova、Fedor A Lakhvich

  DOI：10.1016/s0040-4039(01)00534-2

  日期：2001.5

  A new three-step route to 2-alkyl substituted Δ2-butenolides from 3-alkyltetronic acids is described.

  一种新的三步路线2 -烷基取代的Δ 2个从3- alkyltetronic酸-butenolides进行说明。
• 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.