14-acetoxy-β-caryophyllene | 163956-14-7

• 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: 14-acetoxy-β-caryophyllene
• CAS: 163956-14-7
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: XLKYRVILZQUEJC-IAGRGRHTSA-N

物化性质

• 沸点：
  338.0±21.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  14-acetoxy-β-caryophyllene 在 二甲基硫 、 臭氧 作用下， 生成 Acetic acid 4-[(1R,4S)-2,2-dimethyl-4-(1-methylene-4-oxo-butyl)-cyclobutyl]-2-oxo-butyl ester
  参考文献：
  名称：

  Stereochemistry of 14-hydroxy-β-caryophyllene and related compounds

  摘要：

  The isomerization of beta-caryophyllene (3), under treatment with SeO2, is described. Chemical correlations, between 3 and 14-hydroxy-beta-caryophyllene (6) from Juniperus oxycedrus, are established. High resolution H-1 NMR spectra and analysis by molecular mechanics of 3, 6 and 14-acetoxy-beta-taryophyllene (1) indicate the existence of two conformational isomers, beta alpha and beta beta, in each compound. At 25 degrees C, the beta alpha conformer predominates in 3 and 7 but the beta beta conformer predominates in 6. The higher percentage of 6 beta beta possibly derives from an intramolecular hydrogen bond. The treatment of 3, 6 and 7 with m-CPBA generates, in each case, two diastereomeric 4,5-epoxi-derivatives. The epoxides obtained from 6 have been isolated and analysed separately.

  DOI：

  10.1016/0040-4020(95)00104-g
• 作为产物：
  描述：

  14-hydroxy-4,5-dihydro-caryophyllene 、 乙酸酐 以 吡啶 为溶剂， 生成 14-acetoxy-β-caryophyllene
  参考文献：
  名称：

  Stereochemistry of 14-hydroxy-β-caryophyllene and related compounds

  摘要：

  The isomerization of beta-caryophyllene (3), under treatment with SeO2, is described. Chemical correlations, between 3 and 14-hydroxy-beta-caryophyllene (6) from Juniperus oxycedrus, are established. High resolution H-1 NMR spectra and analysis by molecular mechanics of 3, 6 and 14-acetoxy-beta-taryophyllene (1) indicate the existence of two conformational isomers, beta alpha and beta beta, in each compound. At 25 degrees C, the beta alpha conformer predominates in 3 and 7 but the beta beta conformer predominates in 6. The higher percentage of 6 beta beta possibly derives from an intramolecular hydrogen bond. The treatment of 3, 6 and 7 with m-CPBA generates, in each case, two diastereomeric 4,5-epoxi-derivatives. The epoxides obtained from 6 have been isolated and analysed separately.

  DOI：

  10.1016/0040-4020(95)00104-g

文献信息

• Palladium catalyzed aerobic oxidation for the incorporation of an olfactory group on naturally occurring β-caryophyllene
  作者：Amanda de Camargo Faria、Taciano A. dos Santos Wanderley、Eduardo E. Alberto、Elena V. Gusevskaya

  DOI：10.1016/j.apcata.2017.07.042

  日期：2017.11

  selective oxidation of β-caryophyllene by molecular oxygen using the chloride-free Pd(OAc)2/p-benzoquinone (BQ) catalytic system has been developed. The reaction gives two main products, both arising from the allylic oxidation of the sterically encumbered endocyclic double bond, whereas the terminal double bond of the substrate remains intact. The catalytic process efficiently operates under 10 atm

  β-石竹烯是倍半萜烯中最广泛的一种，在各种香精油（例如copaiba油）中被发现是主要的碳氢化合物，在民间药中已使用多年，在巴西药品出口中占有重要地位。使用无氯的Pd（OAc）2 / p新型的分子氧选择性氧化β-石竹烯-已开发了苯并醌（BQ）催化系统。该反应产生两个主要产物，两者均由空间上受累的环内双键的烯丙基氧化产生，而底物的末端双键保持完整。在不存在通常在相关系统中使用的辅助金属助催化剂的情况下，催化过程可在10atm的氧气下有效地进行。该反应也可以在大气压下在Cu（OAc）2存在下发生，以加速对氧苯醌被分子氧的再氧化。两种由β获得的乙酸烯丙酯-石竹烯在这两个系统中的总收率为75-85％，是一些植物精油中的天然化合物，并具有明显的香料特性。据我们所知，本工作报道了这些功能化的倍半萜化合物的首次合成，这些化合物可能用作合成香料和药理组合物的成分。