(+/-)-(2S^*,3S^*)-2,3-epoxy-2-methylpentan-1-ol | 225110-92-9

• 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: (+/-)-(2S^*,3S^*)-2,3-epoxy-2-methylpentan-1-ol
• 英文别名: (3-Ethyl-2-methyloxiran-2-yl)methanol
• CAS: 225110-92-9
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: OCGUAQREEINKDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(2S^*,3S^*)-2,3-epoxy-2-methylpentan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (2R,3S)-3-ethyl-2-methyl-oxirane-2-carbaldehyde
  参考文献：
  名称：

  Palladium-catalyzed selective hydrogenolysis of alkenyloxiranes with formic acid. Stereoselectivity and synthetic utility

  摘要：

  DOI：

  10.1021/ja00198a045
• 作为产物：
  描述：

  (2E)-2-methyl-2-penten-1-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 苯 为溶剂， 生成 (+/-)-(2S^*,3S^*)-2,3-epoxy-2-methylpentan-1-ol
  参考文献：
  名称：

  Palladium-catalyzed selective hydrogenolysis of alkenyloxiranes with formic acid. Stereoselectivity and synthetic utility

  摘要：

  DOI：

  10.1021/ja00198a045

文献信息

• Lead(IV) acetate mediated cleavage of β-hydroxy ethers: enantioselective synthesis of α-acetoxy carbonyl compounds
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Esteban Alvarez、Ramón Alvarez-Manzaneda、Pedro E. Muñoz、Fermín Jimenez、Hanane Bouanou

  DOI：10.1016/j.tet.2011.09.056

  日期：2011.11

  α-Acetoxy aldehydes or α-acetoxy ketones can be efficiently synthesized by treating 2,3-epoxy primary alcohols with lead tetraacetate. The reaction, which proceeds with complete regio- and stereoselectivity facilitates the enantioselective synthesis of α-acetoxy carbonyl compounds from allyl alcohols, via Sharpless epoxidation. Cyclic β-hydroxy ethers, with an oxygenated five-, six- or seven-membered

  通过用四乙酸铅处理2，3-环氧伯醇可以有效地合成α-乙酰氧基醛或α-乙酰氧基酮。以完全的区域和立体选择性进行的反应有助于通过Sharpless环氧化由烯丙醇对映体选择性合成α-乙酰氧基羰基化合物。具有氧化的五元，六元或七元环的环状β-羟基醚被转化为α-乙酰氧基醚。
• Catalytic Asymmetric Epoxidation of α-Branched Enals
  作者：Olga Lifchits、Corinna M. Reisinger、Benjamin List

  DOI：10.1021/ja1037935

  日期：2010.8.4

  An asymmetric catalytic epoxidation of alpha-branched, alpha,beta-unsaturated aldehydes is presented. A highly synergistic combination of a primary cinchona-based amine and a chiral phosphoric acid was found to promote the reaction with excellent enantiocontrol for alpha-monosubstituted and alpha,beta-disubstituted enals.

  介绍了 α-支链、α、β-不饱和醛的不对称催化环氧化。发现基于伯金鸡纳的胺和手性磷酸的高度协同组合可促进反应，对 α-单取代和 α，β-二取代的烯醛具有优异的对映控制。
• Synthesis of (1S,2R,5R)-2-Ethyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane, the Aggregation Pheromone of Male Beech Bark Beetles,Taphrorychus bicolor (Col., Scol.)
  作者：Wittko Francke、Frank Schröder、Ulrich Kohnle、Matthias Simon

  DOI：10.1002/jlac.199619961005

  日期：1996.10

  acetal 2-ethyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane (1), identified as an aggregation pheromone of males of the beech bark beetle, Taphrorychus bicolor, was determined by unambiguous synthesis and NMR experiments. The syntheses of the racemates of both diastereomers and of optically pure samples are described. The natural product proved to show (1S,2R,5R) configuration.

  新的双环缩醛2-乙基-1,5-二甲基-6,8-二氧杂双环的绝对构型[3.2.1]辛烷（1），确定为山毛榉小蠹，雄性的聚集信息素Taphrorychus双色，是通过明确的合成和NMR实验确定。描述了非对映异构体和光学纯样品的外消旋体的合成。天然产物证明显示（1 S，2 R，5 R）构型。
• Simple Primary Anilines as Iminium Catalysts for the Epoxidation of α-Substituted Acroleins
  作者：Anniina Erkkilä、Petri M. Pihko、Melanie-Rose Clarke

  DOI：10.1002/adsc.200700048

  日期：2007.4.2

  Simple ortho-alkylated anilines have been shown to be excellent iminium catalysts for the epoxidation reaction of α-substituted acroleins. A range of different α-substituted acroleins give the epoxide products in good to excellent yields and good chemoselectivity.

  对于α-取代的丙烯醛的环氧化反应，简单的邻烷基化苯胺已被证明是极好的亚胺催化剂。一系列不同的α-取代的丙烯醛使环氧产物的收率高至优异，并具有良好的化学选择性。
• Method of Inducing Chirality to Epoxides Using 2,3:4,6 di-O-isopropylidene-2-keto-L-gulonic Acid Monohydrate
  申请人：Goswami Amrit

  公开号：US20100136635A1

  公开（公告）日：2010-06-03

  The present invention relates to a recyclable method to prepare chirally pure epoxides directly from olefins using a novel chiral acid 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate as chiral inducer and anhydrous hydrogen peroxide in the form of urea hydrogen peroxide adduct (UHP) as oxidant and lipase enzyme as catalyst. Under the influence of lipase, the chiral acid 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate is converted to per-acid in situ by the oxidant urea hydrogen peroxide which in turn transfers oxygen to olefin inducing chirality to the product epoxide. Using this technique, important epoxide building blocks of different industrially important compounds can be prepared with good yield and moderate enantioselectivity. Chiral epoxidation of olefins with environment friendly catalytic system that can be recycled is highly desirable in the context of Green Chemistry for preparation of many industrially important compounds.

  本发明涉及一种可回收的方法，使用新型手性酸2,3:4,6-二-O-异丙基亚甲基-2-酮-L-古洛酸单水合物作为手性诱导剂，以尿素过氧化氢加合物（UHP）作为氧化剂，脂肪酶酶作为催化剂，直接从烯烃制备手性纯环氧化物。在脂肪酶的作用下，手性酸2,3:4,6-二-O-异丙基亚甲基-2-酮-L-古洛酸单水合物被氧化剂尿素过氧化氢原位转化为过氧化物，进而将氧转移给烯烃，诱导产物环氧化物的手性。使用这种技术，可以以良好的产率和适度的对映选择性制备不同工业重要化合物的重要环氧化物构建块。在绿色化学的背景下，使用可回收的环保催化体系进行烯烃的手性环氧化是非常理想的，以制备许多工业重要化合物。