2-(3,4,5-三甲氧基苯基)环氧乙烷 | 54767-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(3,4,5-三甲氧基苯基)环氧乙烷
• 英文名称: 3,4,5-trimethoxystyrene oxide
• 英文别名: 2-(3,4,5-trimethoxyphenyl)oxirane
• CAS: 54767-81-6
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: WXBAEPCTXMEJNV-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  127-129 °C(Press: 4-5 Torr)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4,5-三甲氧基苯基)环氧乙烷 在 titanium(IV) isopropylate 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-methyl-3,4,5-trimethoxyphenethylamine
  参考文献：
  名称：

  Solvolysis, Electrochemistry, and Development of Synthetic Building Blocks from Sawdust

  摘要：

  Either aldehyde or cinnamyl ether products can be selectively extracted from raw sawdust by controlling the temperature and pressure of a solvolysis reaction. These materials have been used as platform chemicals for the synthesis of 15 different synthetic substrates. The conversion of the initial sawdust-derived materials into electron-rich aryl substrates often requires the use of oxidation and reduction chemistry, and the role electrochemistry can play as a sustainable method for these transformations has been defined.

  DOI：

  10.1021/acs.joc.5b01776
• 作为产物：
  描述：

  2-溴-1-(3,4,5-三甲氧基苯基)乙酮 在 sodium borohydrid 作用下， 以 甲醇 为溶剂， 生成 2-(3,4,5-三甲氧基苯基)环氧乙烷
  参考文献：
  名称：

  Propenone derivatives

  摘要：

  本发明涉及以下式(I)所代表的丙酮衍生物：##STR1##其中R.sup.1代表氢、取代或未取代的较低烷基、取代或未取代的芳基，或YR.sup.5（其中Y代表S或O；R.sup.5代表取代或未取代的较低烷基、取代或未取代的芳基、取代或未取代的杂芳基，或取代或未取代的环氧基残基）；R.sup.2和R.sup.3独立地代表氢、较低烷基，或取代或未取代的芳基烷基，或者R.sup.2和R.sup.3结合形成取代或未取代的亚甲基或乙烯基；R.sup.4代表氢、羟基、较低烷基、取代或未取代的芳基烷基、较低烷氧基、取代或未取代的芳基烷氧基，或卤素；X代表取代或未取代的吲哚基；或其药学上可接受的盐。

  公开号：

  US05952355A1

文献信息

• S-Methylidene agents: preparation of chiral non-racemic heterocycles
  作者：David C. Forbes、Sampada V. Bettigeri、Samit A. Patrawala、Susanna C. Pischek、Michael C. Standen

  DOI：10.1016/j.tet.2008.10.019

  日期：2009.1

  Reaction of sulfur ylide with aldehyde, imine, and ketone functionality affords the desired three-membered heterocycle in excellent yield. The sulfur ylide is generated in situ upon decarboxylation of carboxymethylsulfonium betaine functionality. Of the seven carboxymethylsulfonium betaine derivatives surveyed, the highest level of conversion of π-acceptor to heterocycle was obtained with the one having

  硫叶立德与醛、亚胺和酮官能团的反应以优异的产率提供所需的三元杂环。在羧甲基锍甜菜碱官能团脱羧后原位生成硫叶立德。在调查的七种羧甲基锍甜菜碱衍生物中，π-受体转化为杂环的水平最高，其中含有S-甲基和S-苯基官能团与硫代乙酸酯衍生物结合。涉及羧甲基锍甜菜碱官能团脱羧的亚甲基氮丙啶化和环氧化以反应方案、转化水平和范围的优势补充了现有技术。虽然在亚胺官能团的氮丙啶化中观察到中等水平的非对映控制，但使用 Jacobsen 的 Co(II)-salen 络合物解析的四种环氧乙烷均以高产率和对映选择性获得。分离出的手性非外消旋环氧乙烷分别以 3-溴-4-甲氧基苯甲醛和 3,4,5-三甲氧基苯甲醛为原料，正式合成 chelonin B 和考布他汀。
• Synthesis of 2-hydroxy-2-phenylethylamino derivatives as potential α-adrenergic blocking agents
  作者：M. Alvarez、R. Granados、R. Lavilla、M. Salas

  DOI：10.1002/jhet.5570220326

  日期：1985.5

  synthesis of N,N'-bis[6-(2-hydroxy-2-phenylethylamino)hexyl] cystamines 4, and N-(2-hydroxy-2-phenylethyl)-1,6-hexanediamines 6 are described. Compounds 4 were obtained by condensation of the requisite epoxide 2 with 3-(6-aminohexyl)-1,3-thiazolidine followed by dimerization with opening of the thiazolidine ring. A similar method was used for the preparation of compounds 6. In order to prepare 4j (N,N'-bis6-[2-hydroxy-2(3

  合成N，N'-双[6-（2-羟基-2-苯乙氨基）己基] cystamines 4，和N-（2-羟基-2-苯乙基）-1,6- hexanediamines 6中描述。通过将必需的环氧化物2与3-（6-氨基己基）-1，3-噻唑烷缩合，然后通过打开噻唑烷环进行二聚来获得化合物4。用类似的方法制备化合物6。为了制备4j（N，N′-双6- [2-羟基-2（3，4-二羟基苯基）乙基氨基]己基}胱胺），有几种方法。经过测试 选择的方法涉及使用两个羟基都被保护为甲氧基甲基醚的3，4-二羟基苯甲醛。
• Molecular Iodine in Aqueous Ammonia: Oxidative Fragmentation of Oxiranes to Nitriles
  作者：Ravindra R. Jadhav、Krishnacharya G. Akamanchi

  DOI：10.1246/cl.2013.162

  日期：2013.2.5

  Oxiranes undergo oxidative fragmentation, when treated with iodine in aqueous ammonia, to give nitriles. The reaction goes via formation of 1,2-amino alcohols as intermediates followed by C–C bond cleavage. Advantages of the method are use of off-the-shelf nonexplosive, unlike previously used potentially explosive o-iodoxybenzoic acid, reagents, mild reaction conditions, and easy work-up procedure.

  环氧乙烷在碘和氨水的作用下，会发生氧化性断裂，生成腈。反应过程首先生成1,2-氨基醇中间体，随后发生C-C键断裂。该方法的优势在于使用现成的非爆炸性试剂，与先前使用的潜在爆炸性的邻碘氧基苯甲酸不同，而且反应条件温和，后处理简便。
• Efficient Conversion of Epoxides into β-Hydroperoxy Alcohols Catalyzed by Antimony Trichloride/SiO₂
  作者：Zhan-Hui Zhang、Tong-Shuang Li、Yu-Heng Liu

  DOI：10.1055/s-0028-1083147

  日期：——

  Efficient ring-opening of various epoxides with hydrogen peroxide, catalyzed by antimony trichloride/SiO2, afforded the corresponding β-hydroperoxy alcohols in good to excellent yields under mild reaction conditions. The reactions were efficiently promoted by ultrasound irradiation.

  在三氯化锑/二氧化硅催化下，各种环氧化物与过氧化氢的高效开环反应在温和的反应条件下得到了相应的 δ-hydroperoxy 醇，收率从良好到极佳。超声辐照有效地促进了反应的进行。
• 2,4-diaryl-1,3-dithiolanes; 2,4-diaryl-1,3-dioxolanes;
  申请人：Center for Innovative Technology

  公开号：US05530141A1

  公开（公告）日：1996-06-25

  2,4-Diaryl-1,3-dithiolanes; 2,4-diaryl-1,3-dioxolanes; 2,4-diaryl-1,3-oxathiolanes; and 2,5-diaryl-1,3-oxathiolanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.

  本发明公开了2,4-二芳基-1,3-二硫杂环己烷；2,4-二芳基-1,3-二氧杂环己烷；2,4-二芳基-1,3-氧硫杂环己烷；以及2,5-二芳基-1,3-氧硫杂环己烷，这些化合物能够减少多形核白细胞在炎症或免疫反应期间化学趋化和呼吸爆发，从而导致有害氧自由基的形成。这些化合物通过作为PAF受体拮抗剂、抑制酶5-脂氧合酶或表现出双重活性，即作为PAF受体拮抗剂和5-脂氧合酶抑制剂而表现出这种生物活性。本发明还公开了一种治疗由PAF或白三烯介导的疾病的方法，包括在药学可接受的载体中投予上述识别化合物或其药学可接受的盐的有效量，可选地在药学可接受的载体中。