(1R,3S)-(+)-3-(Trifluoromethyl)camphonanoyl fluoride | 193280-13-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (1R,3S)-(+)-3-(Trifluoromethyl)camphonanoyl fluoride
• 英文别名: (1R,3S)-(+)-1,2,2-Trimethyl-3-trifluoromethyl-1-cyclopentanoyl fluoride；(1R,3S)-1,2,2-trimethyl-3-(trifluoromethyl)cyclopentane-1-carbonyl fluoride
• CAS: 193280-13-6
• 化学式: C₁₀H₁₄F₄O
• 分子量: 226.214
• InChiKey: RSQXABKTMHLEDZ-RCOVLWMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3S)-(+)-3-(Trifluoromethyl)camphonanoyl fluoride 在 氢氧化钾 作用下， 反应 16.0h， 以100%的产率得到(1R,3S)-(+)-3-(Trifluoromethyl)camphonanic acid
  参考文献：
  名称：

  Selective fluorination of (1R,3S)-(+)-camphoric acid with sulphur tetrafluoride. Preparation of fluorinated optically active derivatives of 1,2,2-trimethylcyclopentane

  摘要：

  Treatment of (1R,3S)-(+)-camphoric acid (1) with sulphur tetrafluoride at ambient temperature gives, in general, three products: 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanoyl fluoride (2), 2,2,4,4-tetrafluoro-1,8,8-trimethyl-3-oxa-bicyclo[3.2.1] octane (3) and camphoroyl difluoride (4). The ratio of products strongly depends on the reaction time. Alkaline hydrolysis of (2) gives 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanecarboxylic acid (5),quantitatively. All products exhibit optical activity.

  DOI：

  10.1016/s0022-1139(97)00016-x
• 作为产物：
  描述：

  D-樟脑酸 在 sulfur tetrafluoride 作用下， 反应 0.5h， 以88%的产率得到(1R,3S)-1,2,2-三甲基-1,3-环戊烷二羰基二氟化物
  参考文献：
  名称：

  Selective fluorination of (1R,3S)-(+)-camphoric acid with sulphur tetrafluoride. Preparation of fluorinated optically active derivatives of 1,2,2-trimethylcyclopentane

  摘要：

  Treatment of (1R,3S)-(+)-camphoric acid (1) with sulphur tetrafluoride at ambient temperature gives, in general, three products: 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanoyl fluoride (2), 2,2,4,4-tetrafluoro-1,8,8-trimethyl-3-oxa-bicyclo[3.2.1] octane (3) and camphoroyl difluoride (4). The ratio of products strongly depends on the reaction time. Alkaline hydrolysis of (2) gives 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanecarboxylic acid (5),quantitatively. All products exhibit optical activity.

  DOI：

  10.1016/s0022-1139(97)00016-x

文献信息

• EXPEDIENT SYNTHESIS OF (1R,3S)-(+)-3-(TRIFLUOROMETHYL)CAMPHONANIC ACID AND DERIVATIVES
  作者：Wojciech Dmowski、Krystyna Piasecka-Maciejewska

  DOI：10.1080/00304949909355713

  日期：1999.4
• Selective fluorination of (1R,3S)-(+)-camphoric acid with sulphur tetrafluoride. Preparation of fluorinated optically active derivatives of 1,2,2-trimethylcyclopentane
  作者：Wojciech Dmowski、Tomasz Kozłowski

  DOI：10.1016/s0022-1139(97)00016-x

  日期：1997.7

  Treatment of (1R,3S)-(+)-camphoric acid (1) with sulphur tetrafluoride at ambient temperature gives, in general, three products: 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanoyl fluoride (2), 2,2,4,4-tetrafluoro-1,8,8-trimethyl-3-oxa-bicyclo[3.2.1] octane (3) and camphoroyl difluoride (4). The ratio of products strongly depends on the reaction time. Alkaline hydrolysis of (2) gives 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanecarboxylic acid (5),quantitatively. All products exhibit optical activity.