isovellerol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: isovellerol
• 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-ol
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: JPFARHSFKRUMBZ-SZNYSYDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	13-Hydroxymarasm-7(8)-en-5-oic acid γ-lactone	141947-36-6	C15H20O2	232.323
  ——	(1aα,3aβ,6aβ,6bα)-(+/-)-dimethyl 3a,4,5,6,6a,6b-hexahydro-5,5,6b-trimethylcyclopropindene-1a,2(1H)-dicarboxylate	126753-76-2	C17H24O4	292.375
  ——	(1aα,3aβ,6aβ,6bα)-(+/-)-methyl 2-formyl-3a,4,5,6,6a,6b-hexahydro-5,5,6b-trimethyl-1H-cyclopropindene-1a-carboxylate	143347-42-6	C16H22O3	262.349

反应信息

• 作为产物：
  描述：

  异绒白乳菇醛 在 fungal enzim 作用下， 生成 isovellerol
  参考文献：
  名称：

  拟建的俄科化学防御系统中的新倍半萜

  摘要：

  除了已知的倍半萜烯醛外，还从胡椒乳杆菌，托米诺氏梭菌和红菇（大型真菌）的提取物中分离出了内酰胺哌啶1和哌拉洛尔2。

  DOI：

  10.1016/s0040-4039(00)98646-5

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.
• New sesquiterpenes in a proposed russulaceae chemical defense system
  作者：Olov Sterner、Rolf Bergman、Claes Franzén、Börje Wickberg

  DOI：10.1016/s0040-4039(00)98646-5

  日期：1985.1

  In addition to already known sesquiterpene aldehydes, the lactaranes piperdial 1 and piperalol 2 were isolated from extracts of Lactarius piperatus, L. torminosus and Russula queletii (larger fungi).

  除了已知的倍半萜烯醛外，还从胡椒乳杆菌，托米诺氏梭菌和红菇（大型真菌）的提取物中分离出了内酰胺哌啶1和哌拉洛尔2。