5-ethoxy-4,5-dihydro-4-phenylfuran-2(3H)-one | 78920-27-1

• 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: 5-ethoxy-4,5-dihydro-4-phenylfuran-2(3H)-one
• 英文别名: 5-Ethoxy-4-phenyloxolan-2-one
• CAS: 78920-27-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: XOEYRPUAYRUTID-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 0.05 Torr)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-ethoxy-4,5-dihydro-4-phenylfuran-2(3H)-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 sodium 4-hydroxy-3-phenylbutanoate
  参考文献：
  名称：

  Analogs of .gamma.-hydroxybutyric acid. Synthesis and binding studies

  摘要：

  Substituted 4-hydroxybutyric (GHB) or trans-4-hydroxycrotonic acids (T-HCA) and structurally related compounds were synthesized and submitted to [3H]GHB binding. Structure-activity relationships studies highlighted for [3H]GHB binding (a) the necessity of a nonlactonic, relatively extended conformation of the gamma-hydroxybutyric chain, (b) the existence of some bulk tolerance in the vicinity of the hydroxyl group, and (c) the high sensitivity toward isosteric replacements of the carboxyl or the hydroxyl groups. T-HCA has been recently identified as a naturally occurring substance in the central nervous system (CNS) and shows a better affinity than GHB. Our findings are in favor of the presence in the CNS of specific GHB binding sites, which are different from the GABA and the picrotoxin binding sites, and for which T-HCA may be an endogenous ligand.

  DOI：

  10.1021/jm00400a001
• 作为产物：
  描述：

  3-phenyl-4-ethoxy-2-butenolide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到5-ethoxy-4,5-dihydro-4-phenylfuran-2(3H)-one
  参考文献：
  名称：

  Lactone chemistry. Synthesis of .beta.-substituted, .gamma.-functionalized butan- and butenolides and succinaldehydic acids from glyoxylic acid

  摘要：

  DOI：

  10.1021/jo00337a013

文献信息

• Breukelman, Stephen P.; Meakins, G. Denis, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1627 - 1636
  作者：Breukelman, Stephen P.、Meakins, G. Denis

  DOI：——

  日期：——
• BOURGUIGNON, J. J.;WERMUTH, C. G., J. ORG. CHEM., 1981, 46, N 24, 4889-4894
  作者：BOURGUIGNON, J. J.、WERMUTH, C. G.

  DOI：——

  日期：——
• BREUKELMAN, S. P.;MEAKINS, G. D.;ROE, A. M., J. CHEM. SOC. PERKIN TRANS., 1985, N 8, 1627-1635
  作者：BREUKELMAN, S. P.、MEAKINS, G. D.、ROE, A. M.

  DOI：——

  日期：——