(4S)-4-(2-bromoisopropyl)-1-(2-chloro-3,3,3-trifluoropropyl)cyclohexene | 767357-07-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4S)-4-(2-bromoisopropyl)-1-(2-chloro-3,3,3-trifluoropropyl)cyclohexene
• 英文别名: (4S)-4-(2-bromopropan-2-yl)-1-(2-chloro-3,3,3-trifluoropropyl)cyclohexene
• CAS: 767357-07-3
• 化学式: C₁₂H₁₇BrClF₃
• 分子量: 333.619
• InChiKey: UODZXRBPYVWDRJ-YHMJZVADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.83
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-4-(2-bromoisopropyl)-1-(2-chloro-3,3,3-trifluoropropyl)cyclohexene 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以34%的产率得到(4S)-1-(2-chloro-3,3,3-trifluoropropyl)-4-(isopropenyl)cyclohexene
  参考文献：
  名称：

  Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to β-pinene

  摘要：

  Sodium dithionite effectively promotes the addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to the exocyclic double bond of beta-pinene. The reaction proceeded in an MeCN/H2O system to give almost quantitatively a 1: 1 mixture of diastereoisomers of 4-(2-bromoisopropyl)-1-(2-chloro-3,3,3-trifluoropropyl)-cyclohexene (1). Dehydrobromination of 1 with pyridine gave a mixture of regioisomeric dienes 2 and 3, while treatment with DBU at elevated temperature resulted in total dehydrohalogenation to give trienes 4 and 5. Reduction of 1 with Bu3SnH gave 1-(2-chloro-3,3,3-trifluoropropyl)-4-(isopropyl)cyclohexene (6) which on dehydrochlorination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afforded conjugated diene, 4-isopropyl-1-(trans-3,3,3-trifluoropropenyl)-cyclohexene (7), with 50% overall yield. All the transformations proceeded with the retention of configuration at the carbon atom C-4 and the final compound 7 exhibited high optical activity. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.03.001
• 作为产物：
  描述：

  氟烷 、 beta-pinene 在 sodium dithionite 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 1.25h， 以82.5%的产率得到(4S)-4-(2-bromoisopropyl)-1-(2-chloro-3,3,3-trifluoropropyl)cyclohexene
  参考文献：
  名称：

  Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to β-pinene

  摘要：

  Sodium dithionite effectively promotes the addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to the exocyclic double bond of beta-pinene. The reaction proceeded in an MeCN/H2O system to give almost quantitatively a 1: 1 mixture of diastereoisomers of 4-(2-bromoisopropyl)-1-(2-chloro-3,3,3-trifluoropropyl)-cyclohexene (1). Dehydrobromination of 1 with pyridine gave a mixture of regioisomeric dienes 2 and 3, while treatment with DBU at elevated temperature resulted in total dehydrohalogenation to give trienes 4 and 5. Reduction of 1 with Bu3SnH gave 1-(2-chloro-3,3,3-trifluoropropyl)-4-(isopropyl)cyclohexene (6) which on dehydrochlorination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afforded conjugated diene, 4-isopropyl-1-(trans-3,3,3-trifluoropropenyl)-cyclohexene (7), with 50% overall yield. All the transformations proceeded with the retention of configuration at the carbon atom C-4 and the final compound 7 exhibited high optical activity. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.03.001

文献信息

• Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to β-pinene
  作者：Wojciech Dmowski、Jolanta Ignatowska、Krystyna Piasecka-Maciejewska

  DOI：10.1016/j.jfluchem.2004.03.001

  日期：2004.7

  Sodium dithionite effectively promotes the addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to the exocyclic double bond of beta-pinene. The reaction proceeded in an MeCN/H2O system to give almost quantitatively a 1: 1 mixture of diastereoisomers of 4-(2-bromoisopropyl)-1-(2-chloro-3,3,3-trifluoropropyl)-cyclohexene (1). Dehydrobromination of 1 with pyridine gave a mixture of regioisomeric dienes 2 and 3, while treatment with DBU at elevated temperature resulted in total dehydrohalogenation to give trienes 4 and 5. Reduction of 1 with Bu3SnH gave 1-(2-chloro-3,3,3-trifluoropropyl)-4-(isopropyl)cyclohexene (6) which on dehydrochlorination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afforded conjugated diene, 4-isopropyl-1-(trans-3,3,3-trifluoropropenyl)-cyclohexene (7), with 50% overall yield. All the transformations proceeded with the retention of configuration at the carbon atom C-4 and the final compound 7 exhibited high optical activity. (C) 2004 Elsevier B.V. All rights reserved.