clovan-2β-ol | 62560-57-0

• 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: clovan-2β-ol
• CAS: 62560-57-0
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: NMXIRPDQDDCGRJ-VIRABCJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 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：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  clovan-2β-ol 、 苯甲酰氯 生成 2c-benzoyloxy-(5rH)-clovane
  参考文献：
  名称：

  倍半萜。第六部分 石竹烯的绝对构型

  摘要：

  DOI：

  10.1039/jr9540004665
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium ethanolate 、 肼 作用下， 生成 clovan-2β-ol
  参考文献：
  名称：

  倍半萜。第六部分 石竹烯的绝对构型

  摘要：

  DOI：

  10.1039/jr9540004665

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。
• Heteropoly acid-catalyzed β-caryophyllene chemical transformations: Synthesis route of value-added commercial products from components found in biorenewable resources
  作者：Marcelly M. B. Silva、Camila G. Vieira、Kelly A. da Silva Rocha

  DOI：10.1016/j.mcat.2023.113302

  日期：2023.8

  its processes for obtaining inputs not produced in sufficient quantity by nature, or with superior physicochemical properties to those of compounds acquaintances. This work reports the chemical transformation of β-caryophyllene, a sesquiterpene present in biorenewable materials, using the commercial heteropoly acid catalyst H3PW12O40. The process performed under conditions technologically and environmentally

  将更可持续的催化过程应用于生物可再生衍生物生产的不同反应是化学工业的一个重要趋势，化学工业需要不断更新其过程以获得自然界无法产生的足够数量的投入，或者具有优于熟人化合物的物理化学性质。这项工作报告了使用商用杂多酸催化剂 H 3 PW 12 O 40对生物可再生材料中存在的倍半萜烯 β-石竹烯进行的化学转化. 该过程在技术和环境吸引力的条件下进行，使用危害较小的酮类溶剂（2-丁酮和丙酮）。通过伴随水化反应的异构化反应，得到的产物为(-)-丁香烯、β-丁香酚和β-氯烷醇，总收率为70-80%。所有这些产品在精细化工行业的不同领域都有已知的应用，无论是分离形式还是混合物形式。与 β-石竹烯相比，(-)-Clovene 和 β-caryolanol 具有显着更高的商业价值。β-氯烷醇有已知的应用，尽管该化合物尚未商业化，这使得此处描述的过程对于工业规模的生产具有吸引力。H 3 PW 12 O 40显示出优于传统无机酸催化剂H
• 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：——
• 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.
• Stereospecific syntheses of deuterated clovane and caryolane derivatives related to the cyclization of caryophyllene
  作者：Fred Y. Edamura、Alex Nickon

  DOI：10.1021/jo00830a055

  日期：1970.5