terpinene monoxide | 17023-74-4

• 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: terpinene monoxide
• 英文别名: 1,2-Epoxy-p-menthon-(4)；4,5-Epoxy-1-isopropyl-4-methyl-1-cyclohexene；1-methyl-4-propan-2-yl-7-oxabicyclo[4.1.0]hept-3-ene
• CAS: 17023-74-4
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: JVQQTQFGLBPBSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  γ-松油烯 在 水 、 N,N,N,N-tetraethylammonium tetrafluoroborate 、 sodium bromide 作用下， 以 乙腈 为溶剂， 以15%的产率得到terpinene monoxide
  参考文献：
  名称：

  在溴化物介导的电化学过程中使用电作为可再生能源进行烯烃环氧化

  摘要：

  电化学溴化物介导的烯烃环氧化是原位生成自由可用溴 (FAB) 的可行策略同时通过避免使用化学氧化剂和减少有害试剂的使用来最大程度地减少工艺浪费。在此，提出了一种电化学溴化物介导的烯烃环氧化反应，其中溴化物起着双重作用，既作为电解质，又作为即使在中等阳极电压下也很容易被氧化的介质。引入季铵盐作为有机电解质。调整施加的电荷量以及电解质和烯烃的浓度以最大化反应的效率和选择性。以高达 93% 的高产率获得了 1,2-环氧环己烷等目标化合物，并证明了广泛的底物范围。此外，该过程可以避免形成二溴化物（例如, 1,2-二溴环己烷），它们通常是不受欢迎的死端产品。

  DOI：

  10.1039/d2gc02883b

文献信息

• 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。
• Purification method of phosphoric esters
  申请人：DAIHACHI CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0690063A1

  公开（公告）日：1996-01-03

  A purification method of a phosphoric ester, which comprises treating a crude phosphoric ester with an epoxy compound, heating the resultant in the presence of water, washing the resultant with water, and removing the residual water. The obtained phosphoric esters have low acid value and are excellent in physical properties such as heat resistance, resistance to hydrolysis and storage stability, and are useful as plasticizers and/or flame-retardants.

  一种磷酸酯的提纯方法，包括用环氧化合物处理粗磷酸酯，在有水的情况下加热所得产物，用水洗涤所得产物，然后除去残留的水。得到的磷酸酯酸值低，物理性能优异，如耐热性、抗水解性和储存稳定性，可用作增塑剂和/或阻燃剂。
• Selective Oxidation of Monoterpenes with Hydrogen Peroxide Catalyzed by Peroxotungstophosphate (PCWP)
  作者：Satoshi Sakaguchi、Yutaka Nishiyama、Yasutaka Ishii

  DOI：10.1021/jo960275q

  日期：1996.1.1

  Catalytic epoxidation of monoterpenes with aqueous hydrogen peroxide catalyzed by peroxotung-stophosphate (PCWP) under biphase conditions using chloroform as the solvent was examined. A variety of terpenes was oxidized to the corresponding monoepoxides or diepoxides in good yields under mild conditions. For example, limonene (1) was converted into limonene oxide (la) in which the cyclohexene double bond was selectively epoxidized in almost quantitative yield. The oxidation of gamma-terpinene (2) with 2.2 equiv of 35% H2O2 took place with high stereoselectivity to give cis-diepoxide 2c. In terpenes bearing electron-withdrawing groups such as neryl acetate (3), geranyl acetate (4), citral (5), and geranyl nitrile (6), the double bonds remote from the substituents were epoxidized in preference to the others. The epoxidation of linalool (9) by the present catalyst-oxidant system produced the cyclic products, hydroxy furan 9a and hydroxy pyran 9b, rather than epoxide. tert-Butyl alcohol was successfully employed as the solvent by treating a hydrogen peroxide solution of tert-butyl alcohol with MgSO4 prior to use. The regioselectivities in the epoxidation of monoterpenes can be favorably explained from the electron densities of the double bonds which were estimated using the CAChe system.
• US5616768A
  申请人：——

  公开号：US5616768A

  公开（公告）日：1997-04-01
• Olefin epoxidation using electricity as renewable power in a bromide-mediated electrochemical process
  作者：Hongyang Tang、Jef R. Vanhoof、Dirk De Vos

  DOI：10.1039/d2gc02883b

  日期：——

  Electrochemical bromide-mediated olefin epoxidation is a viable strategy to generate freely available bromine (FAB) in situ while minimizing process waste by avoiding chemical oxidants and reducing the use of hazardous reagents. Herein, an electrochemical bromide-mediated olefin epoxidation is presented, wherein bromide plays a double role, as an electrolyte, but also as a mediator that is easily oxidized

  电化学溴化物介导的烯烃环氧化是原位生成自由可用溴 (FAB) 的可行策略同时通过避免使用化学氧化剂和减少有害试剂的使用来最大程度地减少工艺浪费。在此，提出了一种电化学溴化物介导的烯烃环氧化反应，其中溴化物起着双重作用，既作为电解质，又作为即使在中等阳极电压下也很容易被氧化的介质。引入季铵盐作为有机电解质。调整施加的电荷量以及电解质和烯烃的浓度以最大化反应的效率和选择性。以高达 93% 的高产率获得了 1,2-环氧环己烷等目标化合物，并证明了广泛的底物范围。此外，该过程可以避免形成二溴化物（例如, 1,2-二溴环己烷），它们通常是不受欢迎的死端产品。