ethyl (3R,4S,5S)-5-hydroxy-2-methyl-3-phenyl-5-(trifluoromethyl)-1,2-oxazolidine-4-carboxylate | 138536-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: ethyl (3R,4S,5S)-5-hydroxy-2-methyl-3-phenyl-5-(trifluoromethyl)-1,2-oxazolidine-4-carboxylate
• CAS: 138536-04-6
• 化学式: C₁₄H₁₆F₃NO₄
• 分子量: 319.281
• InChiKey: GLBJBXFOTOHOLE-MDZLAQPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (3S,4R,5S)-2-Methyl-3-phenyl-5-trifluoromethyl-5-trimethylsilanyloxy-isoxazolidine-4-carboxylic acid ethyl ester 以55%的产率得到ethyl (3R,4S,5S)-5-hydroxy-2-methyl-3-phenyl-5-(trifluoromethyl)-1,2-oxazolidine-4-carboxylate
  参考文献：
  名称：

  1, 3-Dipolar cycloaddition between ethyl trifluoroacetoacetate and N-(benzylidene)methylamine N-oxide

  摘要：

  The 1,3-dipolar cycloaddition between ethyl trifluoroacetoacetate and N-(benzylidene)methylamine N-oxide, performed in boiling toluene, leads regio- and stereo-selectively to an isoxazolidine, while the corresponding ethyl acetoacetate is found to be unreactive under the same conditions. On the other hand, alpha-trifluoromethylstyrene behaves as alpha-methylstyrene and affords two diastereoisomeric trifluoromethyl-substituted cycloadducts.

  DOI：

  10.1039/p19910002888

文献信息

• Improvements in 1,3-dipolar cycloaddition of nitrones to fluorinated dipolarophiles under solvent-free microwave activation
  作者：André Loupy、Alain Petit、Danièle Bonnet-Delpon

  DOI：10.1016/0022-1139(95)03330-6

  日期：1995.12

  1,3-Dipolar cycloadditions between ethyl trifluoracetoacetate or α-trifluoromethylstyrene and N-(benzylidene)methylamineN-oxide were performed in the absence of solvent. Under microwave irradiation in a monomode Maxidigest Prolabo reactor, quantitative yields were obtained within 3 min. Compared to conventional heating under the same conditions, the yields are significantly increased (from 55%–64%

  在不存在溶剂的情况下，在三氟乙酰乙酸乙酯或α-三氟甲基苯乙烯与N-（亚苄基）甲胺N-氧化物之间进行1,3-偶极环加成。在单模Maxidigest Prolabo反应器中进行微波辐照时，在3分钟内获得了定量产率。与相同条件下的常规加热相比，产率显着提高（从55％–64％增至88.98％）。现在，使用沸腾甲苯的经典条件（24-48小时内达到65％）得到了显着改善。
• Trifluoromethylalkenes in cycloaddition reactions
  作者：Danièle Bonnet-Delpon、Jean-Pierre Bégué、Thierry Lequeux、Michèle Ourevitch

  DOI：10.1016/0040-4020(95)00885-c

  日期：1996.1

  CF3-Substituted alkenes have been described to be good partners in Diels-Alder reactions with the Danishefsky's diene and in 1,3-dipolar cycloadditions with nitrones and non-stabilized azomethine ylides. The influence of the CF3-group on both the activation of the double bond and the stereochemistry of the cycloaddition has been evaluated. New CF3-substituted mono- and polycyclic compounds 4 and 7, highly functionalized isoxazolidines 18, 19, 22 and 23 and pyrrolidines 12, 13 and 16 have been prepared.
• 1, 3-Dipolar cycloaddition between ethyl trifluoroacetoacetate and N-(benzylidene)methylamine N-oxide
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Thierry Lequeux

  DOI：10.1039/p19910002888

  日期：——

  The 1,3-dipolar cycloaddition between ethyl trifluoroacetoacetate and N-(benzylidene)methylamine N-oxide, performed in boiling toluene, leads regio- and stereo-selectively to an isoxazolidine, while the corresponding ethyl acetoacetate is found to be unreactive under the same conditions. On the other hand, alpha-trifluoromethylstyrene behaves as alpha-methylstyrene and affords two diastereoisomeric trifluoromethyl-substituted cycloadducts.