(-)-α-panasinsen

• 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: (-)-α-panasinsen
• 英文别名: α-panasinsene；Alpha-Panasinsen；(2aS,4aR,8aS)-2,2,4a,8-tetramethyl-1,2a,3,4,5,6-hexahydrocyclobuta[i]indene
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: WHXUZXDWQKUIJL-CFVMTHIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (-)-α-panasinsen 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 生成 Panasinsan A/B
  参考文献：
  名称：

  The Sesquiterpenes of Ginseng

  摘要：

  对人参的倍半萜进行了研究。对挥发油中的 15 种化合物进行了鉴定。其中三个化合物，即 α-花生烯、β-花生烯和β-新花生烯是新化合物，本文对其进行了表征。Panasinsenes 被认为是叶绿素与新烯烃异构化过程中的中间化合物。

  DOI：

  10.1246/bcsj.48.2078
• 作为产物：
  描述：

  (2aS,4aR,8R)-2,2,4a,8-tetramethyl-2a,3,4,5,6,7-hexahydro-1H-cyclobuta[i]inden-8-ol 在 吡啶 、 氯化亚砜 作用下， 反应 0.17h， 以28%的产率得到(2aS,4aR,8aR)-2,2,4A-三甲基-8-亚甲基十氢环丁[c]茚
  参考文献：
  名称：

  Rearrangement of (-)-.beta.-Caryophyllene. A Product Analysis and Force Field Study

  摘要：

  The rearrangement of (-)-beta-caryophyllene (1) with sulfuric acid in ether has been reinvestigated. In the early stage, a multitude of products is formed. Of these, fourteen hydrocarbons (3, 4, 6-17) and four alcohols (5, 18-20) were obtained pure. From the very beginning, the tricycloundecenes 15-17 accumulate quickly. This indicates that a previously unknown rearrangement of 1 by protonation of the exocyclic double bond followed by transannular ring closure is a main reaction, and that the conformation beta alpha is involved. Three hydrocarbons (3, 4, 8) and three alcohols (5, 18, 19) proved to be stable. They are the main components in the late stage. A complete rearrangement scheme followed from a force field analysis using MMP2. First, all conformations up to 4 kcal above the global minimum of each product and each carbenium ion necessary for its formation were detected automatically using the search program HUNTER. Second, the conformation favoring a specific transformation was searched for. For transannular cyclizations, the conformation with the shortest distance between the atoms to be bound and, for ring openings and 1,2-shifts, the conformation with the smallest dihedral angle between the empty p-orbital and the bond to be broken were selected. In all cases, the selection criteria proved valid: The stereochemistry of the conformations selected matched the stereochemistry of the products observed. On the basis of the results presented, a fully automated search prog ram for favorable rearrangement paths may be developed.

  DOI：

  10.1021/ja00141a009

文献信息

• Rearrangement of (-)-.beta.-Caryophyllene. A Product Analysis and Force Field Study
  作者：Lutz Fitjer、Andreas Malich、Carola Paschke、Sabine Kluge、Ralf Gerke、Beate Rissom、Joerg Weiser、Mathias Noltemeyer

  DOI：10.1021/ja00141a009

  日期：1995.9

  The rearrangement of (-)-beta-caryophyllene (1) with sulfuric acid in ether has been reinvestigated. In the early stage, a multitude of products is formed. Of these, fourteen hydrocarbons (3, 4, 6-17) and four alcohols (5, 18-20) were obtained pure. From the very beginning, the tricycloundecenes 15-17 accumulate quickly. This indicates that a previously unknown rearrangement of 1 by protonation of the exocyclic double bond followed by transannular ring closure is a main reaction, and that the conformation beta alpha is involved. Three hydrocarbons (3, 4, 8) and three alcohols (5, 18, 19) proved to be stable. They are the main components in the late stage. A complete rearrangement scheme followed from a force field analysis using MMP2. First, all conformations up to 4 kcal above the global minimum of each product and each carbenium ion necessary for its formation were detected automatically using the search program HUNTER. Second, the conformation favoring a specific transformation was searched for. For transannular cyclizations, the conformation with the shortest distance between the atoms to be bound and, for ring openings and 1,2-shifts, the conformation with the smallest dihedral angle between the empty p-orbital and the bond to be broken were selected. In all cases, the selection criteria proved valid: The stereochemistry of the conformations selected matched the stereochemistry of the products observed. On the basis of the results presented, a fully automated search prog ram for favorable rearrangement paths may be developed.
• The Sesquiterpenes of Ginseng
  作者：Kazuo Yoshihara、Yoshio Hirose

  DOI：10.1246/bcsj.48.2078

  日期：1975.7

  The sesquiterpenes of ginseng have been studied. From the volatile oil, fifteen compounds were characterized. Three of those compounds, α-panasinsene,β-panasinsene and β-neoclovene, were new compounds and were characterized in this paper. Panasinsenes are considered as intermedial compounds in isomerization of caryophyllene to neoclovene.

  对人参的倍半萜进行了研究。对挥发油中的 15 种化合物进行了鉴定。其中三个化合物，即 α-花生烯、β-花生烯和β-新花生烯是新化合物，本文对其进行了表征。Panasinsenes 被认为是叶绿素与新烯烃异构化过程中的中间化合物。