caryophyllene oxide

• 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: caryophyllene oxide
• 英文别名: (-)-caryophyllene epoxide；caryophylene oxide；β-caryohylline oxide；(1R,4R,10S)-4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.0(4,6)]dodecane；(1R,4R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: NVEQFIOZRFFVFW-CZPDGURSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 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：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  caryophyllene oxide 在 aluminum oxide 、 硫酸 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.17h， 以0.24 g的产率得到caryophylladienol II
  参考文献：
  名称：

  Tkachev, A. V.; Gatilov, Yu. V.; Bagryanskaya, I. Yu., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 3, p. 490 - 503

  摘要：

  DOI：
• 作为产物：
  描述：

  β-caryophyllene 在 phosphotungstic acid 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 生成 caryophyllene oxide
  参考文献：
  名称：

  Chromium(III) Terephthalate Metal Organic Framework (MIL-101): HF-Free Synthesis, Structure, Polyoxometalate Composites, and Catalytic Properties

  摘要：

  Hybrid materials of the metal-organic framework (MOF), chromium(III) terephthalate (MIL-101), and phosphotungstic acid (PTA) were synthesized in aqueous media in the absence of hydrofluoric acid. XRD analysis of the MIL101/PTA composites indicates the presence of ordered PTA assemblies residing in both the large cages and small pores of MIL-101, which suggests the formation of previously undocumented structures. The MIL101/PTA structure enables a PTA payload 1.5-2 times higher than previously achieved. The catalytic performance of the MIL101/PTA composites was assessed in the Baeyer condensation of benzaldehyde and 2-naphthol, in the three-component condensation of benzaldehyde, 2-naphthol, and acetamide, and in the epoxidation of caryophyllene by hydrogen peroxide. The catalytic efficiency was demonstrated by the high (over 80-90%) conversion of the reactants under microwave-assisted heating. In four consecutive reaction cycles, the catalyst recovery was in excess of 75%, whereas the product yields were maintained above 92%. The simplicity of preparation, exceptional stability, and reactivity of the novel composites indicate potential in utilization of these catalytic matrices in a multitude of catalytic reactions and engineering processes.

  DOI：

  10.1021/cm2034382

文献信息

• Natural product derivatization with β-lactones, β-lactams and epoxides toward ‘infinite’ binders
  作者：Morgan Jouanneau、Sreekumar Vellalath、Guowei Kang、Daniel Romo

  DOI：10.1016/j.tet.2019.04.068

  日期：2019.6

  found in both therapeutics and natural products. Herein we report several strategies for annulation of these motifs onto natural products that are not known to covalently modify their cellular targets. These strategies can facilitate identification of previously unidentified cellular targets or identify novel cellular targets of these natural products. The reported strategies include telescoped synthesis

  β-内酯，β-内酰胺和环氧化物是在治疗剂和天然产物中均发现的优先结构基序。本文中，我们报告了几种将这些基序环化到天然产物上的策略，这些策略尚不共价修饰其细胞靶标。这些策略可以促进鉴定先前未鉴定的细胞靶标或鉴定这些天然产物的新型细胞靶标。报道的策略包括从烯丙醇望远镜合成β-内酯，亲核试剂催化的迈克尔·奥尔多-β-内酯化，以及[2 + 2]β-内酰胺环化，其以复杂的，可商购的含烯烃天然产物为底物。还报道了用环氧化物标记酚类天然产物的新方法。
• New Carbonyl Compounds in the High-Boiling Fraction of Lavender Oil. 2nd Communication
  作者：Roman Kaiser、Dietmar Lamparsky

  DOI：10.1002/hlca.19830660624

  日期：1983.9.21

  In addition to the sesquiterpenoid compounds reported in [1] the in-depth analysis of lavender oil also led to the identification of new constituents with caryophyllane (1–6), cedrane (7 and 8) and other skeletons (9–21). Spectroscopic properties as well as partial syntheses of these compounds are discussed.

  除了在[1]中报道的倍半萜类化合物外，对薰衣草油的深入分析还导致鉴定出了石竹素（1 – 6），雪松（7和8）和其他骨架（9 – 21）的新成分。讨论了这些化合物的光谱性质以及部分合成。
• Iron-Catalyzed Fluoromethylene Transfer from a Sulfonium Reagent
  作者：Arturs Sperga、Dzintars Zacs、Janis Veliks

  DOI：10.1021/acs.orglett.2c01757

  日期：2022.6.24

  transfer from (2,4-dimethylphenyl)(fluoromethyl)(phenyl)sulfonium tetrafluoroborate to unactivated alkenes. The fluorocarbene or fluoromethylene synthon is the smallest “organic” node in a molecular graph of the organofluorine compounds. In this work, we present alternative solution to unavailable fluorodiazomethane (CHFN2), a missing one-carbon C1 piece in fluorine chemistry, by using a fluoromethylsulfonium

  在这里，我们报告了铁卟啉催化的氟亚甲基从 (2,4-二甲基苯基)(氟甲基)(苯基) 锍四氟硼酸盐转移到未活化烯烃的第一个例子。氟卡宾或氟亚甲基合成子是有机氟化合物分子图中最小的“有机”节点。在这项工作中，我们通过使用氟甲基锍试剂提出了替代解决方案，以替代不可用的氟重氮甲烷 (CHFN 2 )，这是氟化学中缺少的单碳 C1 部分。
• Photoexcited nitroarenes for the oxidative cleavage of alkenes
  作者：Alessandro Ruffoni、Charlotte Hampton、Marco Simonetti、Daniele Leonori

  DOI：10.1038/s41586-022-05211-0

  日期：2022.10.6

  The oxidative cleavage of alkenes is an integral process that converts feedstock materials into high-value synthetic intermediates1,2,3. The most viable method to achieve this in one chemical step is with ozone4,5,6,7, which however poses technical and safety challenges owing to the explosive nature of ozonolysis products8,9. Herein, we disclose an alternative approach to achieve oxidative cleavage

  烯烃的氧化裂解是将原料转化为高价值合成中间体的完整过程1,2,3。在一个化学步骤中实现这一目标的最可行的方法是使用臭氧4,5,6,7，然而，由于臭氧分解产物的爆炸性8,9 ，这带来了技术和安全挑战。在此，我们公开了一种使用硝基芳烃和紫光照射实现烯烃氧化裂解的替代方法。我们证明光激发硝基芳烃是有效的臭氧替代物，可以轻松地与烯烃发生自由基[3+2]环加成反应。由此产生的“ N“掺杂”臭氧化物可以安全处理，并在温和水解条件下产生相应的羰基产物。这些特征使得能够在存在广泛的常用有机官能团的情况下控制所有类型的烯烃的裂解。此外，通过利用电子、空间和介导的极性效应，硝基芳烃的结构和功能多样性提供了一个模块化平台，可以在含有一种以上烯烃的底物中获得位点选择性。
• Reductive Cross-Coupling of Olefins via a Radical Pathway
  作者：Wei Zhou、Igor A. Dmitriev、Paolo Melchiorre

  DOI：10.1021/jacs.3c11285

  日期：2023.11.22