Oxiranemethanol, 3-[2-(3,3-dimethyloxiranyl)ethyl]-3-methyl-, acetate | 79238-73-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Oxiranemethanol, 3-[2-(3,3-dimethyloxiranyl)ethyl]-3-methyl-, acetate
• 英文别名: 2,3:6,7-diepoxy-3,7-dimethyloctyl acetate；cis-2,3:6,7-Diepoxy-3,7-dimethyloctyl Acetate；2,6-diepoxy-3,7-dimethyl-octan-1-ol acetate
• CAS: 79238-73-6；81520-62-9；81520-63-0
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: AHPZYAGHNPQCBR-YWTFCRFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  51.36
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙酸香叶酯 在 Fe(dmp)3 (11a) 氧气 、 异丁醛 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.0h， 以38%的产率得到Oxiranemethanol, 3-[2-(3,3-dimethyloxiranyl)ethyl]-3-methyl-, acetate
  参考文献：
  名称：

  三(1,3-二酮)铁(III)催化烯烃类化合物的好氧环氧化

  摘要：

  三[1,3-双(对甲氧基苯基)-1,3-丙二酮基]铁(III) (Fe(dmp)3) 被发现是许多烯烃化合物（包括苯乙烯类似物和烯烃化合物）氧化的极好催化剂。在室温下结合使用分子氧和醛，将醇以良好到定量的产率转化为相应的环氧化物。

  DOI：

  10.1246/bcsj.64.2513

文献信息

• Direct Epoxidation of Olefins Catalyzed by Nickel(II) Complexes with Molecular Oxygen and Aldehydes
  作者：Tohru Yamada、Toshihiro Takai、Oliver Rhode、Teruaki Mukaiyama

  DOI：10.1246/bcsj.64.2109

  日期：1991.7

  In the presence of a bis(1,3-diketonato)nickel(II) complex, various olefins are directly monooxygenated into the corresponding epoxides on treatment with atmospheric pressure of oxygen or air and aldehydes. Especially, it is noted that bis[1,3-bis(p-methoxyphenyl)-1,3-propanedionato]nickel(II) behaves as an excellent catalyst in the present epoxidation.

  在双(1,3-二酮基)镍(II)配合物存在下，各种烯烃在氧气或空气和醛的常压处理下直接单氧化成相应的环氧化物。特别值得注意的是，双[1,3-双(对甲氧基苯基)-1,3-丙二酮基]镍(II)在本环氧化反应中是一种极好的催化剂。
• Selective epoxidation of monoterpenes with methyltrioxorhenium and H2O2
  作者：Aída L.P. de Villa、Dirk E. De Vos、Consuelo C. de Montes、Pierre A. Jacobs

  DOI：10.1016/s0040-4039(98)01853-x

  日期：1998.11

  terpenes such as α-pinene with H2O2 with minimal rearrangement of the epoxide. Pyridine is also critical to suppress isomerisation of the olefin substrate (in case of nerol, geraniol). The reaction can be directed towards selective single or double epoxidation, or in one step towards the rearranged product (e.g. from linalool to the ring-closure product linalool oxide).

  在吡啶作为助催化剂的存在下，CH 3 ReO 3以最小的环氧基重排催化H 2 O 2对萜烯（如α-pine烯）的环氧化。吡啶对于抑制烯烃底物的异构化也是至关重要的（如果是神经醇，香叶醇）。该反应可以针对选择性的单或双环氧化，或在一步中针对重排的产物（例如从芳樟醇到闭环产物芳樟醇氧化物）。
• The selectivities and the mechanism on highly efficient epoxidation of olefins with 2,6-disubstituted pyridine N-oxides catalyzed by ruthenium porphyrin
  作者：Hiro Ohtake、Tsunehiko Higuchi、Masaaki Hirobe

  DOI：10.1016/s0040-4039(00)92231-7

  日期：1992.4

  Several remarkable selectivities in competitive epoxidations using a ruthenium porphyrin/ 2,6-disubstittuted pyridine N-oxide system were observed. The proposl that the active intermediate of this system differed from the trans-dioxo complex of ruthenium porphyrin was indicated.

  在使用钌卟啉/ 2,6-二取代吡啶N-氧化物体系的竞争性环氧化反应中，观察到了几种显着的选择性。指出了该体系的活性中间体与卟啉钌的反式-二氧杂配合物不同的建议。
• Highly Efficient Method for Epoxidation of Olefms with Molecular Oxygen and Aldehydes Catalyzed by Nickel(II) Complexes
  作者：Tohru Yamada、Toshihiro Takai、Oliver Rhode、Teruaki Mukaiyama

  DOI：10.1246/cl.1991.1

  日期：1991.1

  In the presence of a catalytic amount of a bis(1,3-diketonato)nickel(II) complex, trisubstituted and exo-terminal olefins or norbornene analogues are smoothly monooxygenated into the corresponding epoxides in high to quantitative yields on treatment with aldehyde under an atmospheric pressure of oxygen at room temperature.

  在催化量的双（1,3-二酮基）镍（II）配合物存在下，三取代和外末端烯烃或降冰片烯类似物在用醛处理时顺利单氧化成相应的环氧化物室温下氧气的大气压。
• 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.