1,2-Epoxy-2-methyldecane | 29195-12-8

• 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: 1,2-Epoxy-2-methyldecane
• 英文别名: 2-Methyl-2-octyloxirane；2-methyl-1,2-epoxydecane；1,2-Epoxy-2-methyl-decan
• CAS: 29195-12-8
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: IJIIJXCCQIJKQG-UHFFFAOYSA-N

物化性质

• 沸点：
  208.5±8.0 °C(Predicted)
• 密度：
  0.854±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-Epoxy-2-methyldecane 在 二氯二茂钛 、 锰 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以89%的产率得到2-甲基-1-癸醇
  参考文献：
  名称：

  使用二茂钛 (III)/水系统彻底还原环氧化物：β-氘代醇的合成及其在食品分析中作为内标的用途

  摘要：

  我们描述了使用水作为氢源或使用氧化氘作为氘源的 Cp 2 TiCl 介导的还原性环氧化物开环的综合研究。该反应的显着化学特征允许从不同的环氧化物中获得具有抗马尔科夫尼科夫区域化学的醇。使用 D 2 O 作为氘源可有效合成 β-氘化醇，包括酪醇的氘化样品，酪醇是一种包含在橄榄叶中的生物活性化合物，已成功用作食品分析中的内标.

  DOI：

  10.1002/ejoc.201000487
• 作为产物：
  描述：

  2-癸酮 在 三甲基碘化亚砜 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以78%的产率得到1,2-Epoxy-2-methyldecane
  参考文献：
  名称：

  Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors

  摘要：

  Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase ( complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 structural analogues were prepared and analyzed for their effects on mitochondrial NADH oxidoreductase and NADH oxidase activities. Also measured were the abilities of several of the analogues to inhibit respiration as judged by a shift to glycolysis, and to inhibit the growth of several mammalian cell lines. The nature of the pyrone ring was shown to be important to potency of inhibition, as was the length and nature of substituents in the side chain of the analogues. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.070

文献信息

• Catalytic Asymmetric Synthesis of 2,2-Disubstituted Oxetanes from Ketones by Using a One-Pot Sequential Addition of Sulfur Ylide
  作者：Toshihiko Sone、Gang Lu、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1002/anie.200805473

  日期：——

  Better the second time around: The title compounds were synthesized by using a one‐pot double methylene transfer catalyzed by a heterobimetallic La/Li complex. Chiral amplification in the second step was the key to obtaining oxetanes in high enantiomeric excess (see scheme).

  第二次更好：标题化合物是通过异双金属La / Li络合物催化的一锅法双亚甲基转移合成的。第二步中的手性扩增是获得高对映体过量的氧杂环丁烷的关键（参见方案）。
• Selectivity enhancement of epoxide hydrolase catalyzed resolution of 2,2-disubstituted oxiranes by substrate modification
  作者：Ingrid Osprian、Wolfgang Stampfer、Kurt Faber

  DOI：10.1039/b005203p

  日期：——

  A series of (±)-2,2-disubstituted oxiranes bearing an alkene or alkyne functional group were resolved by bacterial epoxide hydrolases with excellent selectivities. The presence of a carbon–carbon double or triple bond furnished a highly flexible system for substrate modification, which allowed the enantioselectivity to be tuned by rational substrate modification. Thus, a significant selectivity enhancement of more than a ten-fold increase of E-values was achieved by appropriate choice of the C–C multiple bond, i.e. by (i) choosing an alkene or alkyne moiety or by (ii) variation of the E/Z-configuration of olefinic substrates. The enantioenriched epoxides and vicinal diols thus obtained may be easily transformed into ω-functionalized building blocks containing a chiral fully substituted carbon atom by oxidative cleavage of the carbon–carbon multiple bond.

  一系列带有烯烃或炔烃官能团的(±)-2,2-二取代环氧化物通过细菌环氧化物水解酶得到了极佳的选择性拆分。碳-碳双键或三键的存在为底物修饰提供了一个高度灵活的系统，使得通过合理的底物修饰可以调节对映选择性。因此，通过适当选择C-C多重键，即通过（i）选择烯烃或炔烃部分或（ii）改变烯烃底物的E/Z构型，实现了E值超过十倍的显著选择性增强。由此获得的具有对映体富集的环氧化物和邻二醇可以通过碳-碳多重键的氧化断裂，容易地转化为含有手性完全取代碳原子的ω-官能化构建单元。
• Fluorination with ionic liquid EMIMF(HF)2.3 as mild HF source
  作者：Hideaki Yoshino、Kazuhiko Matsumoto、Rika Hagiwara、Yasuhiko Ito、Koichiro Oshima、Seijiro Matsubara

  DOI：10.1016/j.jfluchem.2005.09.016

  日期：2006.1

  Hydrogen fluoride is a basic fluorinating reagent, but handling it is difficult. For this reason, some modified fluorinating reagents such as HF-pyridine, Et3N-HF, and poly(hydrogen fluoride) complex have been developed. Those reagents, however, still require aqueous work-up procedures which generate hydrogen fluoride. Recently, ionic liquids have received much attention because of the ease in handling

  氟化氢是一种基本的氟化试剂，但是处理起来很困难。为此，已经开发了一些改性的氟化试剂，例如HF-吡啶，Et 3 N-HF和聚（氟化氢）络合物。但是，这些试剂仍需要进行水溶液后处理程序，以产生氟化氢。近来，由于易于处理和非水后处理的可能性，离子液体受到了广泛的关注。在空气和湿气中稳定的离子液体3-乙基-1-甲基咪唑鎓低聚氟化氢（EMIMF（HF）2.3）可以用作某些氟化反应的氟化氢当量；它不需要水后处理。
• Aerobic Epoxidation of Olefinic Compounds Catalyzed by Tris(1,3-diketonato)iron(III)
  作者：Toshihiro Takai、Eiichiro Hata、Tohru Yamada、Teruaki Mukaiyama

  DOI：10.1246/bcsj.64.2513

  日期：1991.8

  Tris[1,3-bis(p-methoxyphenyl)-1,3-propanedionato]iron(III) (Fe(dmp)3) was found to be an excellent catalyst for oxygenation of a number of olefinic compounds including styrene analogues and olefinic alcohols into the corresponding epoxides in good to quantitative yields with combined use of molecular oxygen and an aldehyde at room temperature.

  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。
• Cobalt(II) Complex Catalyzed Epoxidation of Olefins by Combined Use of Molecular Oxygen and Cyclic Ketones
  作者：Toshihiro Takai、Eiichiro Hata、Kiyotaka Yorozu、Teruaki Mukaiyama

  DOI：10.1246/cl.1992.2077

  日期：1992.10

  In the presence of a catalytic amount of cobalt(II)-Schiff base complexes, various olefins are smoothly oxygenated into the corresponding epoxides in good to high yields by combined use of an atmospheric pressure of oxygen (oxidant) and cyclic ketones (reductant), such as 2-methylcyclohexanone, under mild conditions.

  在催化量的钴（II）-席夫碱配合物的存在下，通过氧（氧化剂）和环酮（还原剂）的常压组合使用，各种烯烃以良好到高产率顺利氧化成相应的环氧化物，如 2-甲基环己酮，在温和条件下。