(3S,R_S)-(E)-1-ethoxy-3-trifluoromethyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-ene | 170118-69-1

• 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: (3S,R_S)-(E)-1-ethoxy-3-trifluoromethyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-ene
• 英文别名: (E,2S)-4-ethoxy-1,1,1-trifluoro-2-[[(R)-(4-methylphenyl)sulfinyl]methyl]but-3-en-2-ol
• CAS: 170118-69-1
• 化学式: C₁₄H₁₇F₃O₃S
• 分子量: 322.348
• InChiKey: OLDTXNCMOJJVOO-CGFBJWSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  65.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,R_S)-(E)-1-ethoxy-3-trifluoromethyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-ene 在 三氟乙酸酐 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以94%的产率得到(E)-(S)-4-Ethoxy-1,1,1-trifluoro-2-p-tolylsulfanylmethyl-but-3-en-2-ol
  参考文献：
  名称：

  Synthesis and use of (E)-1-ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-enes

  摘要：

  Condensation of the lithium salt of (R)-methyl p-tolyl sulfoxide 1 with fluorinated alpha,beta-unsaturated ketones 2 leads to (3R/S,R(s),)-(E)-1-ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-enes 3, whose absolute stereochemistry was determined by X-ray diffraction and NMR analyses. Reductive removal of the sulfinyl chiral auxiliary allows the preparation of both enantiomers of fluorinated tertiary alcohols of type 8 and 9.

  DOI：

  10.1039/p19950001667
• 作为产物：
  描述：

  (R)-(+)-甲基对甲苯砜 、 1-乙氧基-3-三氟甲基-1,3-丁二烯 在 lithium diisopropyl amide 作用下， 生成 (E,2R)-4-ethoxy-1,1,1-trifluoro-2-[[(R)-(4-methylphenyl)sulfinyl]methyl]but-3-en-2-ol 、 (3S,R_S)-(E)-1-ethoxy-3-trifluoromethyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-ene
  参考文献：
  名称：

  Synthesis and use of (E)-1-ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-enes

  摘要：

  Condensation of the lithium salt of (R)-methyl p-tolyl sulfoxide 1 with fluorinated alpha,beta-unsaturated ketones 2 leads to (3R/S,R(s),)-(E)-1-ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-enes 3, whose absolute stereochemistry was determined by X-ray diffraction and NMR analyses. Reductive removal of the sulfinyl chiral auxiliary allows the preparation of both enantiomers of fluorinated tertiary alcohols of type 8 and 9.

  DOI：

  10.1039/p19950001667

文献信息

• Arnone, Alberto; Bravo, Pierfrancesco; Bruche, Luca, Journal of Chemical Research - Part S, 1996, # 4, p. 198 - 199
  作者：Arnone, Alberto、Bravo, Pierfrancesco、Bruche, Luca、Seresini, Paolo

  DOI：——

  日期：——
• Synthesis and use of (E)-1-ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-enes
  作者：Pierfrancesco Bravo、Luca Bruché、Alessandra Farina、Igor I. Gerus、Maria T. Kolytcheva、Valery P. Kukhar、Stefano Valdo Meille、Fiorenza Viani

  DOI：10.1039/p19950001667

  日期：——

  Condensation of the lithium salt of (R)-methyl p-tolyl sulfoxide 1 with fluorinated alpha,beta-unsaturated ketones 2 leads to (3R/S,R(s),)-(E)-1-ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-enes 3, whose absolute stereochemistry was determined by X-ray diffraction and NMR analyses. Reductive removal of the sulfinyl chiral auxiliary allows the preparation of both enantiomers of fluorinated tertiary alcohols of type 8 and 9.