pyrovellerofuran | 69905-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七呋喃
• 英文名称: pyrovellerofuran
• CAS: 69905-56-2
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: NSEGVMZMLVIRTH-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  13.14
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  异绒白乳菇醛 在 溶剂黄146 作用下， 生成 pyrovellerofuran
  参考文献：
  名称：

  Marasmane倍半萜烯（+）-异戊二烯的热重排机理。通过分子内烯反应进行环丙烷闭环

  摘要：

  真菌倍半萜异戊二醛（2）到（1）的可逆热转化是通过双环烯醇（3）进行的独特的分子内烯反应，这通过动力学研究，氘掺入和（3）的俘获得以证明。

  DOI：

  10.1039/c39900001260

文献信息

• The structure of a novel sesquiterpene furna alcohol with a lactarane skeleton
  作者：Jan Kihlberg、Rolf Bergman、Liselott Nilsson、Olov Sterner、Börgje Wickberg

  DOI：10.1016/s0040-4039(00)85975-4

  日期：1983.1

  The exomethylene furan alcohol 2, which is formed when fatty acid esters of velutinal 1 isolated from Lactarius species are degraded on silica gel, correlates the absolute configuration of isovelleral 5a with that of other sesquiterpenes isolated from Lactarius sp.

  当从乳杆菌属物种分离的维他命1的脂肪酸酯在硅胶上降解时形成的exomethyl呋喃醇2使异黄酮5a的绝对构型与从乳杆菌属物种分离的其他倍半萜的绝对构型相关。
• The mechanism of the thermal rearrangement of the marasmane sesquiterpene (+)-isovelleral. Cyclopropane ring closure via an intramolecular ene reaction
  作者：Thomas Hansson、Rolf Bergman、Olov Sterner、B�rje Wickberg

  DOI：10.1039/c39900001260

  日期：——

  The reversible thermal conversion of the fungal sesquiterpene Isovelleral (2) into (1) is a unique Intramolecular ene reaction proceeding via the bicyclic enol (3), which is demonstrated by kinetic studies, deuterium incorporation, and the trapping of (3).

  真菌倍半萜异戊二醛（2）到（1）的可逆热转化是通过双环烯醇（3）进行的独特的分子内烯反应，这通过动力学研究，氘掺入和（3）的俘获得以证明。
• The thermal isomerization of the sesquiterpenes isovelleral and merulidial. A reversible ring opening of the cis-methylcyclopropanecarboxaldehyde group via an intramolecular ene reaction.
  作者：Thomas Hansson、Olov Sterner、Boerje Wickberg、Rolf Bergman

  DOI：10.1021/jo00040a020

  日期：1992.7

  Fungal sesquiterpene dialdehydes of marasmane and isolactarane types, such as isovelleral (1) and merulidial (7), undergo a reversible thermal rearrangement to products (e.g., 2 and 8) with inverted orientations of the cyclopropane rings. The process is shown to involve an intramolecular ene reaction with a bicyclic enol intermediate 13 which was trapped as an E-silyl ether 17. In the presence of D2O, deuterium is incorporated quantitatively into the C-12 methyl groups of 1 and 2. A high kinetic isotope effect is observed for the rearrangement of 1 and its deuterated analogue 24, and the reaction parameters are comparable to those reported for the thermal ring-opening reactions of cis-alkylvinylcyclopropanes and cis-alkyl cyclopropyl ketones. In the presence of weak acid or base, an equilibrium is established between 1, 2, and the hydroazulenic dialdehydes 14 and 15. Dialdehyde 7 reacts less cleanly and incorporates deuterium not only at C-13 but also at C-1 (26). The latter process presumably involves enolization via a [1,5] sigmatropic hydrogen shift.