(R_S)-(Z)-2-methoxy-1-<(4-methylphenyl)sulphinyl>-3,3,3-trifluoropropene | 167010-81-3

• 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: (R_S)-(Z)-2-methoxy-1-<(4-methylphenyl)sulphinyl>-3,3,3-trifluoropropene
• 英文别名: 1-<(4-methylphenyl)sulphinyl>-3,3,3-trifluoro-2-propanone methyl enol ether；1-methyl-4-[(R)-[(Z)-3,3,3-trifluoro-2-methoxyprop-1-enyl]sulfinyl]benzene
• CAS: 167010-81-3
• 化学式: C₁₁H₁₁F₃O₂S
• 分子量: 264.268
• InChiKey: WJVUCGCQANMIED-CGQZWFTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-N-benzylideneaniline oxide 、 (R_S)-(Z)-2-methoxy-1-<(4-methylphenyl)sulphinyl>-3,3,3-trifluoropropene 生成 2,3-diphenyl-5-methoxy-4-[(4-methylphenyl)sulphinyl]-5-trifluoromethylisoxazolidine
  参考文献：
  名称：

  Synthesis of optically pure fluorosubstituted isoxazolidines by 1,3-dipolar cycloaddition of nitrones to chiral methyl enol ethers of 3-fluoro-1-sulphinyl-2-propanones

  摘要：

  Optically pure enol ether 4 undergoes 1,3-dipolar cycloaddition, with C,N-diphenylnitrone 5 to give the fluorosubstituted isoxazolidine 6 in a fully regio- and diastereoselective manner. The absolute configuration of 6 has been established by X-ray analysis. When changing the nitrone and/or the fluoro substitution pattern in compounds similar to 4, the same reactivity is observed.

  DOI：

  10.1016/s0957-4166(00)80057-9
• 作为产物：
  描述：

  1,1,1-trifluoro-3-[(R)-(4-methylphenyl)sulfinyl]propan-2-one 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以35%的产率得到(R_S)-(Z)-2-methoxy-1-<(4-methylphenyl)sulphinyl>-3,3,3-trifluoropropene
  参考文献：
  名称：

  Fluorinated enol ethers bearing chiral arylsulphinyl groups

  摘要：

  A synthesis of 2-alkoxy-2-fluoroalkyl-1-(p-tolylsulphinyl) ethenes 4 with good regioselectivity from gamma-fluorosubstituted beta-ketosulphoxides 3 is described

  DOI：

  10.1016/0022-1139(95)03262-c

文献信息

• New fluorinated chiral synthons
  作者：Pierfrancesco Bravo、Alessandra Farina、Massimo Frigerio、Stefano Valdo Meille、Fiorenza Viani、Vadim Soloshonok

  DOI：10.1016/0957-4166(94)80049-9

  日期：1994.6

  The syntheses of new optically pure poly-halo and poly-fluoro oxiranes 5b-e by addition of diazomethane on the corresponding beta-keto-gamma-fluorosubstituted sulphoxide intermediates, both in keto 3, hydrate 4 or in keto/ hydrate form are described. Syntheses of sulphur-free fluorinated oxiranes 18b-e, beta-hydroxy-beta-trifluoromethyl amine 21d, alpha-hydroxy-alpha-trifluoromethyl-beta-amino acid 24d, alpha-trifluoromethyl-alpha,beta-dihydroxy acid 25d and beta,gamma-dihpdroxy-beta-trifluoro- and -chlorodifluoromethyl amines 26c and 26d are shown as examples of their chemical versatility
• Fluorinated enol ethers bearing chiral arylsulphinyl groups
  作者：Pierfrancesco Bravo、Luca Bruché、Marcello Crucianelli、Annamaria Merli

  DOI：10.1016/0022-1139(95)03262-c

  日期：1995.9

  A synthesis of 2-alkoxy-2-fluoroalkyl-1-(p-tolylsulphinyl) ethenes 4 with good regioselectivity from gamma-fluorosubstituted beta-ketosulphoxides 3 is described
• Synthesis of optically pure fluorosubstituted isoxazolidines by 1,3-dipolar cycloaddition of nitrones to chiral methyl enol ethers of 3-fluoro-1-sulphinyl-2-propanones
  作者：Pierfrancesco Bravo、Luca Broché、Alessandra Farina、Giovanni Fronza、Stefano Valdo Meille、Annamaria Merli

  DOI：10.1016/s0957-4166(00)80057-9

  日期：1993.10

  Optically pure enol ether 4 undergoes 1,3-dipolar cycloaddition, with C,N-diphenylnitrone 5 to give the fluorosubstituted isoxazolidine 6 in a fully regio- and diastereoselective manner. The absolute configuration of 6 has been established by X-ray analysis. When changing the nitrone and/or the fluoro substitution pattern in compounds similar to 4, the same reactivity is observed.