stearoylvelutinal

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: stearoylvelutinal
• 英文别名: [(1S,3S,4R,8S,9R,11S)-6,6,9-trimethyl-2,13-dioxapentacyclo[9.3.0.01,3.04,8.09,11]tetradecan-12-yl] octadecanoate
• 化学式: C₃₃H₅₆O₄
• 分子量: 516.805
• InChiKey: VRKPUGRREPONNX-PTIMBMRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  37
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  stearoylvelutinal 反应 24.0h， 以32%的产率得到Velleral
  参考文献：
  名称：

  Stereostructure of Plagiochiline A and Conversion of Plagiochiline A and Stearoylvelutinal into Hot-Tasting Compounds by Human Saliva.

  摘要：

  通过 X 射线晶体学分析，确定了从肝草 Plagiochila fruticosa 中分离出来的 plagiochiline A（1）的立体结构。Plagiochiline A 在人体唾液的作用下转化为 plagiochilal B (2) 和 furanoplagiochilal (3)，而从 Lactarius vellerus 真菌中分离出来的硬脂酰绒毛醛 (4) 也在人体唾液的作用下转化为 velleral (5)。

  DOI：

  10.1248/cpb.42.1542
• 作为产物：
  描述：

  十八烷酰氯 、 (+/-)-velutinal 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以63%的产率得到stearoylvelutinal
  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

• Bernardi, Maria De; Fronza, Giovanni; Mellerio, Giorgio, Gazzetta Chimica Italiana, 1984, vol. 114, # 3/4, p. 163 - 168
  作者：Bernardi, Maria De、Fronza, Giovanni、Mellerio, Giorgio、Valla, Vera、Vidari, Giovanni、Vita-Finzi, Paola

  DOI：——

  日期：——
• Stereostructure of Plagiochiline A and Conversion of Plagiochiline A and Stearoylvelutinal into Hot-Tasting Compounds by Human Saliva.
  作者：Toshihiro HASHIMOTO、Hironao TANAKA、Yoshinori ASAKAWA

  DOI：10.1248/cpb.42.1542

  日期：——

  The stereostructure of plagiochiline A (1) isolated from the liverwort Plagiochila fruticosa has been established by X-ray crystallographic analysis. Plagiochiline A was converted into plagiochilal B (2) and furanoplagiochilal (3) by human saliva, and stearoylvelutinal (4) isolated from the fungus Lactarius vellerus was converted into velleral (5), also by human saliva.

  通过 X 射线晶体学分析，确定了从肝草 Plagiochila fruticosa 中分离出来的 plagiochiline A（1）的立体结构。Plagiochiline A 在人体唾液的作用下转化为 plagiochilal B (2) 和 furanoplagiochilal (3)，而从 Lactarius vellerus 真菌中分离出来的硬脂酰绒毛醛 (4) 也在人体唾液的作用下转化为 velleral (5)。
• 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.