2-甲基-2-(4-硝基苯基)环氧乙烷 | 75590-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲基-2-(4-硝基苯基)环氧乙烷
• 英文名称: p-nitro-α-methylstyrene oxide
• 英文别名: 2-methyl-2-(4-nitrophenyl)oxirane
• CAS: 75590-19-1
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: BHJABURPYYGBAY-UHFFFAOYSA-N

物化性质

• 沸点：
  292.1±28.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-2-(4-硝基苯基)环氧乙烷 在 indium(III) chloride 、 (S)-4-(叔丁氧基)-2-甲基-4-氧代丁酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (R)-di-tert-butyl 1-(2-(4-nitrophenyl)-1-oxo-propan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  β-tert-Butyl aspartate as an organocatalyst for the asymmetric α-amination of α,α-disubstituted aldehydes

  摘要：

  The enantioselective alpha-amination reaction of alpha,alpha-disubstituted aldehydes can lead to a variety of enantioenriched amino aldehydes, amino alcohols, and amino acids. After screening a variety of amino acids and their derivatives, we identified a cheap, simple, commercially available aspartic acid derivative that can catalyze efficiently the reaction between alpha,alpha-disubstituted aldehydes and dialkyl azodicarboxylates. The reaction proceeds smoothly leading to the corresponding alpha-aminated adducts in moderate to quantitative yields and moderate to high enantioselectivities (up to 96% ee). Finally, the conversion of these adducts to alpha,alpha-disubstituted quaternary amino acids is also described. 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.103
• 作为产物：
  描述：

  1-isopropenyl-4-nitro-benzene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到2-甲基-2-(4-硝基苯基)环氧乙烷
  参考文献：
  名称：

  [EN] METHODS OF PROMOTING BETA CELL PROLIFERATION
  [FR] PROCÉDÉS DE PROMOTION DE LA PROLIFÉRATION DE CELLULES BÊTA

  摘要：

  本公开提供了促进胰岛细胞增殖的方法。这些方法对于治疗糖尿病和其他以葡萄糖耐量受损为特征的疾病非常有用。

  公开号：

  WO2018106818A1

文献信息

• Microbiological Transformations 43. Epoxide Hydrolases as Tools for the Synthesis of Enantiopure α-Methylstyrene Oxides:  A New and Efficient Synthesis of (<i>S</i>)-Ibuprofen
  作者：M. Cleij、A. Archelas、R. Furstoss

  DOI：10.1021/jo982101+

  日期：1999.7.1

  the enantioselectivity of these biohydrolyses strongly depends on the nature of the enzyme and of the substituent. Using some of these enzymes, this approach allows to prepare these epoxides in high optical purity. The potentiality to perform efficient preparative-scale resolution using such a biocatalyst was illustrated by the four-step synthesis of (S)-ibuprofen, a nonsteroidal antiinflammatory drug

  使用来自不同来源的 10 种环氧化物水解酶研究了在芳环上不同取代的各种 α-甲基苯乙烯氧化物衍生物的生物水解。我们的结果表明，这些生物水解的对映选择性在很大程度上取决于酶和取代基的性质。使用这些酶中的一些，该方法允许以高光学纯度制备这些环氧化物。(S)-布洛芬是一种非甾体抗炎药和家用止痛药，是全球销量前十的药物之一，其四步合成说明了使用这种生物催化剂进行高效制备级拆分的潜力。使用组合化学酶促策略，
• Efficient Catalytic Corey–Chaykovsky Reactions Involving Ketone Substrates
  作者：Sarah A. Kavanagh、Alessandro Piccinini、Stephen J. Connon

  DOI：10.1002/adsc.201000255

  日期：2010.10.9

  demonstrated for the first time that a sulfide catalyst, utilised at 20 mol% loading, can promote methylene transfer to ketones in the presence of methyl triflate and an organic base. This metal-free methodology is of broad scope – both aliphatic and aromatic ketones (including trifluoromethyl ketones) can be converted to synthetically useful terminal epoxides in excellent yields at room temperature.

  首次证明，在三氟甲磺酸甲酯和有机碱的存在下，以20摩尔％的载量使用的硫化物催化剂可促进亚甲基向酮的转移。这种无金属的方法具有广泛的应用范围-脂肪族和芳香族酮（包括三氟甲基酮）都可以在室温下以优异的产率转化为合成有用的末端环氧化物。
• Radical-mediated aerobic oxidation of substituted styrenes and stilbenes
  作者：Hasil Aman、Wei-Hua Chiu、Pin-Heng Liu、Gary Jing Chuang

  DOI：10.1039/d1nj04755h

  日期：——

  A 2,2-azobis(isobutyronitrile)-catalyzed oxidative cleavage of alkenes with molecular oxygen as the oxidant was described. Carbonyl compounds and oxiranes were obtained in moderate yield under mild conditions. This study provided useful insights into the mechanism of aerobic oxidative cleavage of alkenes.

  描述了 2,2-偶氮二（异丁腈）催化烯烃氧化裂解，分子氧作为氧化剂。在温和条件下以中等产率获得羰基化合物和环氧乙烷。该研究为烯烃的有氧氧化裂解机制提供了有用的见解。
• [EN] THIENOPYRIMIDINE AND THIENOPYRIDINE COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE THIÉNOPYRIMIDINE ET DE THIÉNOPYRIDINE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV MICHIGAN

  公开号：WO2016040330A1

  公开（公告）日：2016-03-17

  The present disclosure provides compounds and methods for inhibiting the interaction of menin with its upstream or downstream signaling molecules including but not limited to MLL1, MLL2 and MLL-fusion oncoproteins. Compounds of the disclosure may be used in methods for the treatment of a wide variety of cancers and other diseases associated with one or more of MLL1, MLL2, MLL fusion proteins, and menin.

  本公开提供了抑制menin与其上游或下游信号分子相互作用的化合物和方法，包括但不限于MLL1、MLL2和MLL融合致癌蛋白。本公开的化合物可用于治疗与MLL1、MLL2、MLL融合蛋白和menin之一或多个相关的各种癌症和其他疾病的方法。
• Thienopyrimidine and thienopyridine compounds and methods of use thereof
  申请人：The Regents of the University of Michigan

  公开号：US10246464B2

  公开（公告）日：2019-04-02

  The present disclosure provides compounds and methods for inhibiting the interaction of menin with its upstream or downstream signaling molecules including but not limited to MLL1, MLL2 and MLL-fusion oncoproteins. Compounds of the disclosure may be used in methods for the treatment of a wide variety of cancers and other diseases associated with one or more of MLL1, MLL2, MLL fusion proteins, and menin.

  本公开提供了抑制 menin 与其上游或下游信号分子（包括但不限于 MLL1、MLL2 和 MLL 融合肿瘤蛋白）相互作用的化合物和方法。本公开的化合物可用于治疗与 MLL1、MLL2、MLL 融合蛋白和 menin 中的一种或多种相关的多种癌症和其它疾病。