(R)-2-Methyl-2-octyloxirane | 151284-12-7

• 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: (R)-2-Methyl-2-octyloxirane
• 英文别名: (R)-1,2-epoxy-2-methyldecanol；(2R)-2-methyl-2-octyloxirane
• CAS: 151284-12-7
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: IJIIJXCCQIJKQG-LLVKDONJSA-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：

  (R)-2-Methyl-2-octyloxirane 在 吡啶 、 水 、 silicon tetrafluoride 、 二异丙胺 作用下， 生成 Toluene-4-sulfonic acid (S)-2-fluoro-2-methyl-decyl ester
  参考文献：
  名称：

  New Chiral Dopants Based on the 2-Fluoro-2-Methylalkoxy Tail for Use in Ferroelectric Liquid Crystal Mixtures

  摘要：

  A new class of PLC materials based on the 2-fluoro-2-methylalkoxy tail is reported. This new class of materials consistently shows an N* helical pitch opposite in sign to that of the polarization. These materials are compared to their 2-fluoroalkoxy analogs to explore the methyl group's effect on the N* pitch and polarization.

  DOI：

  10.1080/10587259508033586
• 作为产物：
  描述：

  2-癸酮 在 吡啶 、 正丁基锂 、 AD-mix β 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 16.08h， 生成 (R)-2-Methyl-2-octyloxirane
  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。
• Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors
  作者：Simon J. Leiris、Omar M. Khdour、Zachary J. Segerman、Krystal S. Tsosie、Jean-Charles Chapuis、Sidney M. Hecht

  DOI：10.1016/j.bmc.2010.03.070

  日期：2010.5

  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.
• New Chiral Dopants Based on the 2-Fluoro-2-Methylalkoxy Tail for Use in Ferroelectric Liquid Crystal Mixtures
  作者：Michael D. Wand、William N. Thurmes、Rohini T. Vohra、Kundalika M More、Atsushi Yoshizawa、Toshihiro Hirai、Junko Umezawa

  DOI：10.1080/10587259508033586

  日期：1995.4

  A new class of PLC materials based on the 2-fluoro-2-methylalkoxy tail is reported. This new class of materials consistently shows an N* helical pitch opposite in sign to that of the polarization. These materials are compared to their 2-fluoroalkoxy analogs to explore the methyl group's effect on the N* pitch and polarization.