(3R,4R,S_S)-5,5,6,6,6-pentafluoro-4-hydroxy-3-(tolylsulfinyl)hexanoic acid | 473435-97-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3R,4R,S_S)-5,5,6,6,6-pentafluoro-4-hydroxy-3-(tolylsulfinyl)hexanoic acid
• 英文别名: (3R,4R)-5,5,6,6,6-pentafluoro-4-hydroxy-3-[(S)-(4-methylphenyl)sulfinyl]hexanoic acid
• CAS: 473435-97-1
• 化学式: C₁₃H₁₃F₅O₄S
• 分子量: 360.302
• InChiKey: OXIWWKYGWSABID-FIPKEAFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  93.8
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3R,4R,S_S)-5,5,6,6,6-pentafluoro-4-hydroxy-3-(tolylsulfinyl)hexanoic acid 在 溶剂黄146 、 三氟乙酸酐 、 sodium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 4.0h， 生成 (4R,5R)-5-pentafluoroethyl-4-(p-tolylthio)dihydrofuran-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Both Enantiomers of Trifluoro-γ-valerolactone and Pentafluoro-γ-caprolactone

  摘要：

  Both enantiomers of 5-(trifluoromethyl)dihydrofuran-2-one (1a) and 5-(pentafluoroethyl)dihydrofuran-2-one (1b) have been synthesised stereoselectively, in four steps, starting from chiral (R)- or (S)-3-[(4-methylphenyl)sulfinyl]propionic acid (2) and commercially available perfluorinated esters. Compound (+)-(S)-1b is the pentafluoro analogue of the aggregation pheromone of Trogoderma glabrum.

  DOI：

  10.1002/1099-0690(200206)2002:12<1895::aid-ejoc1895>3.0.co;2-1
• 作为产物：
  描述：

  (S)-3-[(4-methylphenyl)sulfinyl]propionic acid 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.08h， 生成 (3R,4R,S_S)-5,5,6,6,6-pentafluoro-4-hydroxy-3-(tolylsulfinyl)hexanoic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Both Enantiomers of Trifluoro-γ-valerolactone and Pentafluoro-γ-caprolactone

  摘要：

  Both enantiomers of 5-(trifluoromethyl)dihydrofuran-2-one (1a) and 5-(pentafluoroethyl)dihydrofuran-2-one (1b) have been synthesised stereoselectively, in four steps, starting from chiral (R)- or (S)-3-[(4-methylphenyl)sulfinyl]propionic acid (2) and commercially available perfluorinated esters. Compound (+)-(S)-1b is the pentafluoro analogue of the aggregation pheromone of Trogoderma glabrum.

  DOI：

  10.1002/1099-0690(200206)2002:12<1895::aid-ejoc1895>3.0.co;2-1

文献信息

• Stereoselective Synthesis of Both Enantiomers of Trifluoro-γ-valerolactone and Pentafluoro-γ-caprolactone
  作者：Pierfrancesco Bravo、Massimo Frigerio、Alfonso Melloni、Walter Panzeri、Cristina Pesenti、Fiorenza Viani、Matteo Zanda

  DOI：10.1002/1099-0690(200206)2002:12<1895::aid-ejoc1895>3.0.co;2-1

  日期：2002.6

  Both enantiomers of 5-(trifluoromethyl)dihydrofuran-2-one (1a) and 5-(pentafluoroethyl)dihydrofuran-2-one (1b) have been synthesised stereoselectively, in four steps, starting from chiral (R)- or (S)-3-[(4-methylphenyl)sulfinyl]propionic acid (2) and commercially available perfluorinated esters. Compound (+)-(S)-1b is the pentafluoro analogue of the aggregation pheromone of Trogoderma glabrum.