(1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undec-3-ene | 136296-35-0

• 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: (1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undec-3-ene
• 英文别名: (1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undeca-3-ene；1R,3Z,9S,4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-ene；(1R,3Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-3-ene
• CAS: 136296-35-0
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: NSMRKFBAPAOVQL-RDNHTORASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undec-3-ene 、 硫酸 生成 α-neoclovene
  参考文献：
  名称：

  XOMENKO, T. M.;KORCHAGINA, D. V.;GATILOV, YU. V.;BAGRYANSKAYA, YU. I.;TKA+, ZH. ORGAN. XIMII, 26,(1990) N0, S. 2129-2145

  摘要：

  DOI：
• 作为产物：
  描述：

  caryophyllene oxide 在 lithium aluminium tetrahydride 、 磷酸 、 silica gel 、 四氯化钛 作用下， 生成 β-caryophyllene 、 (1R,3Z,9S)-4,11,11-trimethyl-8-methylenebicyclo<7.2.0>undec-3-ene 、 (1R,9S)-4,8-bismethylenebicyclo<7.2.0>undecane
  参考文献：
  名称：

  Khomenko, T. M.; Korchagina, D. V.; Gatilov, Yu. V., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 10.2, p. 1839 - 1852

  摘要：

  DOI：

文献信息

• Acid-catalyzed isomerization of caryophyllene in the presence of SiO2 and Al2O3 impregnated with sulfuric acid
  作者：E. P. Romanenko、A. V. Tkachev

  DOI：10.1007/s11172-018-2179-3

  日期：2018.6

  The conversion of caryophyllene upon contact with Al2O3 and SiO2 impregnated with sulfuric acid was carried out, and the components of the resulting mixtures were identified. Having in hands such “standard” mixtures greatly facilitates identification of components of sesquiterpene fractions of essential oils and other mixtures of natural origin. The catalytic activity of silica gel impregnated with

  在与硫酸浸渍的 Al2O3 和 SiO2 接触时进行石竹烯的转化，并确定所得混合物的组分。掌握这样的“标准”混合物极大地促进了精油和其他天然来源混合物的倍半萜成分成分的鉴定。用硫酸(H+-SiO2)浸渍的硅胶对石竹烯酸催化异构化的催化活性明显高于H+-Al2O3，与浓硫酸的活性相当。
• 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.
• XOMENKO, T. M.;KORCHAGINA, D. V.;GATILOV, YU. V.;BAGRYANSKAYA, YU. I.;TKA+, ZH. ORGAN. XIMII, 26,(1990) N0, S. 2129-2145
  作者：XOMENKO, T. M.、KORCHAGINA, D. V.、GATILOV, YU. V.、BAGRYANSKAYA, YU. I.、TKA+

  DOI：——

  日期：——
• KHOMENKO, T. M.;KORCHAGINA, D. V.;BAGRYANSKAYA, I. YU.;GATILOV, YU. V.;TK+, 12TH CONF. ISOPRENOIDS, PEC POD SNEZKOU, OCT. 4-11, 1987. ABSTR. PAP., PR+
  作者：KHOMENKO, T. M.、KORCHAGINA, D. V.、BAGRYANSKAYA, I. YU.、GATILOV, YU. V.、TK+

  DOI：——

  日期：——
• Khomenko, T. M.; Korchagina, D. V.; Gatilov, Yu. V., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 10.2, p. 1839 - 1852
  作者：Khomenko, T. M.、Korchagina, D. V.、Gatilov, Yu. V.、Bagryanskaya, Yu. I.、Tkachev, A. V.、et al.

  DOI：——

  日期：——