13-Hydroxymarasm-7(8)-en-5-oic acid γ-lactone | 141947-36-6

• 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: 13-Hydroxymarasm-7(8)-en-5-oic acid γ-lactone
• 英文别名: (1S,3R,4S,8S)-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.01,3.04,8]tridec-9-en-13-one
• CAS: 141947-36-6
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: UIIAKAJYKXAUKF-QFEPDWEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  13-Hydroxymarasm-7(8)-en-5-oic acid γ-lactone 在 吡啶 、 四氧化锇 、 sodium hydrogensulfite 作用下， 生成 7α,8α,13-Trihydroxy-marasm-5-oic acid γ-lactone
  参考文献：
  名称：

  Marasmane lactones from Lactarius vellereus

  摘要：

  DOI：

  10.1016/0031-9422(92)80038-g
• 作为产物：
  描述：

  (1aα,3aβ,6aβ,6bα)-(+/-)-methyl 3a,4,5,6,6a,6b-hexahydro-5,5,6b-trimethyl-2<<(trifluoromethyl)sulfonyl>oxy>cyclopropindene-1a(1H)-carboxylate 在 palladium diacetate 二异丁基氢化铝 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 13-Hydroxymarasm-7(8)-en-5-oic acid γ-lactone
  参考文献：
  名称：

  Total synthesis of some marasmane and lactarane sesquiterpenes.

  摘要：

  A general and efficient synthetic route to the marasmane sesquiterpenes (+/-)-isovelleral (2) and (+/-)-stearoylvelutinal (1b) is described. Total syntheses of two other naturally occurring sesquiterpenes, deconjugated anhydrolactarorufin A (5) and lactarorufin A (6), were achieved using an acid-catalyzed ring expansion of lactone 25. All four syntheses are highly stereoselective and do not require the use of any protecting groups. Finally, the protic acid-catalyzed degradation of velutinal (1a) was investigated in an effort to chemically induce the biologically important conversion of velutinal (1a) to isovelleral (2). The experimental results thus obtained indicate that an enzymatic mechanism for the key transformation of velutinal (1a) into isovelleral (2) is more plausible than one that is acid-catalyzed.

  DOI：

  10.1021/jo00048a036

文献信息

• Total synthesis of some marasmane and lactarane sesquiterpenes.
  作者：Scott K. Thompson、Clayton H. Heathcock

  DOI：10.1021/jo00048a036

  日期：1992.10

  A general and efficient synthetic route to the marasmane sesquiterpenes (+/-)-isovelleral (2) and (+/-)-stearoylvelutinal (1b) is described. Total syntheses of two other naturally occurring sesquiterpenes, deconjugated anhydrolactarorufin A (5) and lactarorufin A (6), were achieved using an acid-catalyzed ring expansion of lactone 25. All four syntheses are highly stereoselective and do not require the use of any protecting groups. Finally, the protic acid-catalyzed degradation of velutinal (1a) was investigated in an effort to chemically induce the biologically important conversion of velutinal (1a) to isovelleral (2). The experimental results thus obtained indicate that an enzymatic mechanism for the key transformation of velutinal (1a) into isovelleral (2) is more plausible than one that is acid-catalyzed.
• Marasmane lactones from Lactarius vellereus
  作者：Włodzimierz M. Daniewski、Maria Gumułka、Katarzyna Ptaszyńska、Piotr Skibicki、Janusz Krajewski、Przemysław Gluziński

  DOI：10.1016/0031-9422(92)80038-g

  日期：1992.3