Unii-SL7fad899C

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Unii-SL7fad899C
• 英文别名: ethyl (2S,3R)-3-(4-methylphenyl)oxirane-2-carboxylate
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: UMSHXRVBYUKRDF-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Unii-SL7fad899C 、 N-甲基羟胺盐酸盐 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 0.15h， 以72%的产率得到4-hydroxy-2-methyl-3-p-methylphenylisoxazolidin-5-one
  参考文献：
  名称：

  Regioselective ring opening of β-phenylglycidate and aziridine-2-carboxylates with N-alkylhydroxylamines: synthesis of isoxazolidinones

  摘要：

  A simple and efficient method for the synthesis of 4-hydroxy or 4-alkylamino isoxazolidin-3-ones and 4-hydroxy isoxazolidin-5-ones is described: The synthesis involved the ring opening of ethyl beta-arylglycidates or ethyl N-alkylaziridine-2-carboxylates by free N-alkylhydroxylamines or hydroxylamine anions, followed by cyclization to give the title isoxazolidinones in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.052
• 作为产物：
  描述：

  乙基-p-甲基肉桂酸 在 dibromamine-T 、 水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.92h， 以70%的产率得到Unii-SL7fad899C
  参考文献：
  名称：

  Efficient Protocol for Stereoselective Epoxidation of Cinnamic Esters Using TsNBr₂

  摘要：

  An efficient method has been developed for the synthesis of epoxide from cinnamic esters without any catalyst. The reaction was performed in CH(3)CN-water (4/1) using N,N-dibromo-p-toluenesulfonamide (TsNBr(2)) in alkaline conditions. This procedure can be utilized for stereoselective synthesis of epoxides from cinnamic esters in excellent yield in a shorter reaction time with exclusive formation of the trans-isomer. The method was further extended successfully for styrenes.

  DOI：

  10.1080/00397910903318617

文献信息

• Highly Enantioselective Epoxidation of α,β-Unsaturated Esters by Chiral Dioxirane
  作者：Xin-Yan Wu、Xuegong She、Yian Shi

  DOI：10.1021/ja020478y

  日期：2002.7.1

  This paper describes a highly enantioselective epoxidation of α,β-unsaturated esters using the fructose-derived ketone 2 as catalyst and Oxone as oxidant. High ee's have been obtained for a number of trans and trisubstituted substrates (82−98% ee). The results described show that it is feasible for dioxiranes to effectively epoxidize electron-deficient olefins with high ee's.

  本文描述了使用果糖衍生的酮 2 作为催化剂和 Oxone 作为氧化剂的 α,β-不饱和酯的高度对映选择性环氧化。许多反式和三取代底物 (82-98% ee) 都获得了高 ee。所描述的结果表明，二环氧乙烷有效地环氧化具有高ee值的缺电子烯烃是可行的。
• Regioselective ring opening of β-phenylglycidate and aziridine-2-carboxylates with N-alkylhydroxylamines: synthesis of isoxazolidinones
  作者：Mohamed Ali Tabarki、Rafâa Besbes

  DOI：10.1016/j.tet.2013.12.052

  日期：2014.2

  A simple and efficient method for the synthesis of 4-hydroxy or 4-alkylamino isoxazolidin-3-ones and 4-hydroxy isoxazolidin-5-ones is described: The synthesis involved the ring opening of ethyl beta-arylglycidates or ethyl N-alkylaziridine-2-carboxylates by free N-alkylhydroxylamines or hydroxylamine anions, followed by cyclization to give the title isoxazolidinones in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Efficient Protocol for Stereoselective Epoxidation of Cinnamic Esters Using TsNBr₂
  作者：Indranirekha Saikia、Bishwapran Kashyap、Prodeep Phukan

  DOI：10.1080/00397910903318617

  日期：2010.8.5

  An efficient method has been developed for the synthesis of epoxide from cinnamic esters without any catalyst. The reaction was performed in CH(3)CN-water (4/1) using N,N-dibromo-p-toluenesulfonamide (TsNBr(2)) in alkaline conditions. This procedure can be utilized for stereoselective synthesis of epoxides from cinnamic esters in excellent yield in a shorter reaction time with exclusive formation of the trans-isomer. The method was further extended successfully for styrenes.