1-(3-丁基-2-环氧乙烷基)乙酮 | 17257-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-丁基-2-环氧乙烷基)乙酮
• 英文名称: Z-3,4-epoxy-2-octanone
• 英文别名: 3,4-epoxyoctan-2-one；3,4-epoxy-2-octanone；3,4-Epoxy-octan-2-on；1-(3-butyl-oxiranyl)-ethanone；1-(3-butyloxiran-2-yl)ethanone
• CAS: 17257-80-6
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: VKRREPCLXWIPRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914190090

反应信息

• 作为反应物：
  描述：

  1-(3-丁基-2-环氧乙烷基)乙酮 在 溶剂黄146 、 sodium phenylseleno(triethyl)borate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以100%的产率得到4-羟基辛烷-2-酮
  参考文献：
  名称：

  有机硒介导的α，β-环氧酮，α，β-环氧酯及其同系物还原为β-羟基羰基化合物：合成羟醛及其类似物的新方法

  摘要：

  描述了通过使用有机硒试剂将α，β-环氧酮，α，β-环氧酯（缩水甘油酯）及其同类物还原为β-羟基羰基化合物（醛醇）的新方法。通过在EtOH中用NaBH 4还原（PhSe）2和原位生成的苯硒酚（PhSeH），可以轻松制备苯基硒基（三乙基）硼酸钠复合物Na [PhSeB（OEt）3 ]通过添加乙酸从硼酸盐配合物中得到的氯已被证明可作为这些转化的极好的还原剂。有机硒介导的α，β-环氧羰基化合物在α-碳上区域特异性还原，从而以优异的收率生产出多种环状（分子内）醇醛和非环状（分子间）醇醛。定量机理研究表明，与常见的电子转移还原剂相比，有机硒介导的还原通过α取代过程进行。

  DOI：

  10.1016/s0040-4020(97)00781-3
• 作为产物：
  描述：

  3-辛烯-2-酮 在 (cetylpyridinium)3VMo12O40 双氧水 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 1-(3-丁基-2-环氧乙烷基)乙酮
  参考文献：
  名称：

  Gao, Qiang; Ding, Yong; Liu, Haitao, Journal of Chemical Research, 2005, # 11, p. 716 - 718

  摘要：

  DOI：

文献信息

• Gold Nanoparticle-Catalyzed Environmentally Benign Deoxygenation of Epoxides to Alkenes
  作者：Akifumi Noujima、Takato Mitsudome、Tomoo Mizugaki、Koichiro Jitsukawa、Kiyotomi Kaneda

  DOI：10.3390/molecules16108209

  日期：——

  and green catalytic deoxygenation of epoxides to alkenes using gold nanoparticles (NPs) supported on hydrotalcite [HT: Mg6Al2CO3(OH)16] (Au/HT) with alcohols, CO/H2O or H2 as the reducing reagent. Various epoxides were selectively converted to the corresponding alkenes. Among the novel metal NPs on HT, Au/HT was found to exhibit outstanding catalytic activity for the deoxygenation reaction. Moreover

  我们开发了一种高效、绿色的环氧化物催化脱氧为烯烃的方法，使用负载在水滑石 [HT: Mg6Al2CO3(OH)16] (Au/HT) 上的金纳米粒子 (NPs)，并以醇、CO/H2O 或 H2 作为还原剂。各种环氧化物被选择性地转化为相应的烯烃。在 HT 上的新型金属 NPs 中，发现 Au/HT 对脱氧反应具有出色的催化活性。此外，Au/HT 可以从反应混合物中分离出来并在保留其催化活性和选择性的情况下重复使用。Au/HT 的高催化性能归因于 Au NPs 和 HT 之间的协同作用选择性形成 Au 氢化物物种。
• Supported Gold and Silver Nanoparticles for Catalytic Deoxygenation of Epoxides into Alkenes
  作者：Takato Mitsudome、Akifumi Noujima、Yusuke Mikami、Tomoo Mizugaki、Koichiro Jitsukawa、Kiyotomi Kaneda

  DOI：10.1002/anie.201001055

  日期：——

  Supported gold and silver nanoparticles (NPs), which are well‐known epoxidation catalysts, were found to have intrinsic catalytic ability for the deoxygenation of epoxides into alkenes using alcohol as a reductant (see picture). The selectivity for all the alkenes were over 99 %, and an excellent turnover number was achieved. Furthermore, these supported gold and silver nanoparticles were recyclable.

  以“ O”为例：人们发现，负载的金和银纳米颗粒（NPs）是众所周知的环氧化催化剂，具有使用醇作为还原剂将环氧化物脱氧成烯烃的固有催化能力（参见图片）。所有烯烃的选择性均超过99％，并获得了极佳的周转率。此外，这些负载的金和银纳米颗粒是可回收的。
• Crystal Structure and Catalytic Behavior in Olefin Epoxidation of a One-Dimensional Tungsten Oxide/Bipyridine Hybrid
  作者：Tatiana R. Amarante、Margarida M. Antunes、Anabela A. Valente、Filipe A. Almeida Paz、Martyn Pillinger、Isabel S. Gonçalves

  DOI：10.1021/acs.inorgchem.5b00928

  日期：2015.10.19

  The tungsten oxide/2,2'-bipyridine hybrid material [WO3(2,2'-bpy)]center dot nH(2)O (n = 1-2) (1) has been prepared in near quantitative yield by the reaction of H2WO4, 2,2'-bpy, and H2O in the mole ratio of ca. 1:2:700 at 160 degrees C for 98 h in a rotating Teflon-lined digestion bomb. The solid-state structure of 1 was solved and refined through Rietveld analysis of high-resolution synchrotron X-ray diffraction data collected for the microcrystalline powder. The material, crystallizing in the orthorhombic space group Iba2, is composed of a one-dimensional organic-inorganic hybrid polymer, (1)(infinity)[WO3(2,2'-bpy)], topologically identical to that found in the previously reported anhydrous phases [MO3(2,2'-bpy)] (M = Mo, W). While in the latter the N,N'-chelated 2,2'-bpy ligands of adjacent corner-shared MO4N2} octahedra are positioned on the same side of the 1D chain, in 1 the 2,2'-bpy ligands alternate above and below the chain. The catalytic behavior of compound 1 for the epoxidation of cis-cyclooctene was compared with that for several other tungsten- or molybdenum-based (pre)catalysts, including the hybrid polymer [MoO3(2,2'-bpy)]. While the latter exhibits superior performance when tert-butyl hydropercndde (TBHP) is used as the oxidant, compound 1 is superior when aqueous hydrogen peroxide is used, allowing near-quantitative conversion of the olefin to the epoxide. With H2O2, compounds 1 and [MoO3(2,2'-bpy)] act as sources of soluble active species, namely, the oxodiperoxo complex [MO(O-2)(2)(2,2'-bpy)], which is formed in situ. Compounds 1 and [WO(O-2)(2)(2,2'-bpy)] (2) were further tested in the epoxidation of cydododecene, trans-2-octene, 1-octene, (R)-limonene, and styrene. The structure of 2 was determined by single-crystal X-ray diffraction and found to be isotypical with the molybdenum analogue.
• First lipase catalysed resolution of epoxy enol esters
  作者：Sébastien Gravil、Henri Veschambre、Robert Chênevert、Jean Bolte

  DOI：10.1016/j.tetlet.2006.06.009

  日期：2006.8

  We report the first enzyme-catalysed kinetic resolution of epoxy enol esters. The lipase-promoted hydrolysis of these compounds provided alpha-hydroxyketones or alpha-hydroxyaldehydes (arising from the spontaneous rearrangement of the epoxy enols) and the residual esters with moderate to good enantioselectivity (E up to 100). (c) 2006 Elsevier Ltd. All rights reserved.
• A novel oxidation of internal alkynes with hydrogen peroxide catalyzed by peroxotungsten compounds
  作者：Yasutaka Ishii、Yasuyuki Sakata

  DOI：10.1021/jo00308a002

  日期：1990.10