caryophyllene dioxide | 109120-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: caryophyllene dioxide
• 英文别名: 4,12,12-Trimethylspiro[5-oxatricyclo[8.2.0.04,6]dodecane-9,2'-oxirane]
• CAS: 109120-40-3
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: ITCVFHPZQFFEGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,12,12-三甲基-9-亚甲基-5-氧杂三环[8.2.0.04,6]十二烷 在 sodium tungstate (VI) dihydrate 、 磷酸 、 硫酸 、 三辛基甲基硫酸铵 双氧水 、 sodium sulfate 作用下， 以 水 为溶剂， 反应 12.0h， 以85%的产率得到caryophyllene dioxide
  参考文献：
  名称：

  METHOD FOR MANUFACTURING AN EPOXY COMPOUND AND METHOD FOR EPOXIDIZING A CARBON-CARBON DOUBLE BOND

  摘要：

  本发明提供了一种生产环氧化合物的方法，包括在中性无机盐和钨化合物（a）、磷酸、膦酸及其盐（b）和表面活性剂（c）的混合催化剂存在下，通过过氧化氢氧化有机化合物的碳-碳双键，以及一种环氧化方法，包括在催化剂和中性无机盐存在下，通过过氧化氢氧化碳-碳双键。

  公开号：

  US20120108830A1

文献信息

• Enzymatic epoxidation of β-caryophyllene using free or immobilized lipases or mycelia from the Amazon region
  作者：Jaqueline Maria Ramos da Silva、Thiago Bergler Bitencourt、Marcelo Alves Moreira、Maria da Graça Nascimento

  DOI：10.1016/j.molcatb.2013.05.021

  日期：2013.11

  The chemo-enzymatic epoxidation of the terpene beta-caryophyllene is reported herein. This compound can form two products, the mono-epoxide 2 and the di-epoxide 3. Different experimental conditions, varying the source of the lipases (including mycelia from the Amazon region), the oxidizing agents (H2O2 aq. (AHP) or urea-hydrogen peroxide (UHP)) and the substituted acyl donors on the alkyl chain (bromide and alkyl), along with the influence of organic medium, were evaluated. Depending on the experimental conditions the formation of a single product could be obtained. CAL-B was the most efficient catalyst (conv. >99%). When using the commercial lipases product 2 was obtained in conversions of 16-27%, and using the native lipases 2 was obtained in conversions of 20-23%. With the use of mycelia UEA_06 and UEA_53 the conversions were 16 and 21%, respectively. When the 2-bromo alkylated and 2-ethylhexanoic acids were used as acyl donors only the mono-epoxide 2 was obtained in conversions of 14-54% (24 h). AHP was found to be a better oxidizing agent than UHP, a shorter time and lower amount being required to obtain 2 or 3 as the sole product in good conversions (60 up to >99%). The organic solvents were also selective. When using n-hexane the preferred formation of 2 was observed with >99% conversion, and when ethyl acetate or toluene were used the conversion to 3 was also >99% (in 8 and 24 h, respectively). (c) 2013 Published by Elsevier B.V.
• US8742145B2
  申请人：——

  公开号：US8742145B2

  公开（公告）日：2014-06-03
• METHOD FOR MANUFACTURING AN EPOXY COMPOUND AND METHOD FOR EPOXIDIZING A CARBON-CARBON DOUBLE BOND
  申请人：Takumi Kiyoshi

  公开号：US20120108830A1

  公开（公告）日：2012-05-03

  The present invention provides a method for producing an epoxy compound, comprising oxidizing a carbon-carbon double bond of an organic compound by hydrogen peroxide in the presence of a neutral inorganic salt and a mixed catalyst of a tungsten compound (a), at least one phosphorus compound selected from the group consisting of phosphoric acids, phosphonic acids, and salts thereof (b) and a surfactant (c), and an epoxidizing method comprising oxidizing a carbon-carbon double bond by hydrogen peroxide in the presence of the catalyst and the neutral inorganic salt.

  本发明提供了一种生产环氧化合物的方法，包括在中性无机盐和钨化合物（a）、磷酸、膦酸及其盐（b）和表面活性剂（c）的混合催化剂存在下，通过过氧化氢氧化有机化合物的碳-碳双键，以及一种环氧化方法，包括在催化剂和中性无机盐存在下，通过过氧化氢氧化碳-碳双键。