3-甲基丁内酯 | 78920-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 3-甲基丁内酯
• 英文名称: 3-methylbutyrolactone
• 英文别名: 5-ethoxy-4-methyl-dihydro-furan-2-one；5-Aethoxy-4-methyl-dihydro-furan-2-on；γ-Ethoxy-γ-isovalerolacton；5-Ethoxy-4-methyloxolan-2-one
• CAS: 78920-23-7
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: JHPRICYFXCXKRA-UHFFFAOYSA-N

物化性质

• 沸点：
  65 °C(Press: 1 Torr)
• 密度：
  1.0496 g/cm3(Temp: 16 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  3-甲基丁内酯 生成 二氢-4-甲基 2(3H)-呋喃酮
  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：

  4-甲基-5-羟基呋喃-2-酮 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 20.25h， 生成 3-甲基丁内酯
  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

• Pino et al., Rendiconti - Istituto Lombardo Accademia di Scienze e Lettere, A: Scienze Matematiche, Fisiche, Chimiche e Geologiche, 1954, vol. 87, p. 200,211
  作者：Pino et al.

  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：——
• Analogs of .gamma.-hydroxybutyric acid. Synthesis and binding studies
  作者：Jean Jacques Bourguignon、Angele Schoenfelder、Martine Schmitt、Camille Georges Wermuth、Viviane Hechler、Brigitte Charlier、Michel Maitre

  DOI：10.1021/jm00400a001

  日期：1988.5

  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.
• Lactone chemistry. Synthesis of .beta.-substituted, .gamma.-functionalized butan- and butenolides and succinaldehydic acids from glyoxylic acid
  作者：J. J. Bourguignon、C. G. Wermuth

  DOI：10.1021/jo00337a013

  日期：1981.11