velutinal | 83481-29-2

• 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: velutinal
• 英文别名: 2H,4H-Cycloprop(4,5)oxireno(6,7)indeno(5,6-c)furan-4-ol,octahydro-5a,7,7-trimethyl-, (1aS,4S,4aS,5aR,5bS,8aR,8bS)-；(1S,3S,4R,8S,9R,11S,12S)-6,6,9-trimethyl-2,13-dioxapentacyclo[9.3.0.01,3.04,8.09,11]tetradecan-12-ol
• CAS: 83481-29-2
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: GYCYIRSSVBOBAX-UAMZPEQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  velutinal 在 钾硼氢 作用下， 生成 lactarol
  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
• 作为产物：
  描述：

  6-stearylvelutinal 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 velutinal
  参考文献：
  名称：

  Velutinal esters of lactarius vellereus and L. Necator. The preparation of free velutinal.

  摘要：

  DOI：

  10.1016/s0040-4039(00)81670-6

文献信息

• Basidiomycete sesquiterpenes: the silica gel induced degradation of velutinal derivatives
  作者：Olov Sterner、Rolf Bergman、Jan Kihlberg、James Oluwadiya、Boerje Wickberg、Giovanni Vidari、Maria De Bernardi、Federica De Marchi、Giovanni Fronza、Paola Vita Finzi

  DOI：10.1021/jo00207a008

  日期：1985.4
• 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。
• Velutinal esters of lactarius vellereus and L. Necator. The preparation of free velutinal.
  作者：Olov Sterner、Rolf Bergman、Ewa Kesler、Liselott Nilsson、James Oluwadiya、Börje Wickberg

  DOI：10.1016/s0040-4039(00)81670-6

  日期：1983.1