Dimethyl trans-1,4-bis(difluoromethyl)-1,4-cyclohexanedicarboxylate | 153032-54-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Dimethyl trans-1,4-bis(difluoromethyl)-1,4-cyclohexanedicarboxylate
• 英文别名: trans-dimethyl 1,4-bis(difluoromethyl)-1,4-cyclohexanedicarboxylate
• CAS: 153032-54-3
• 化学式: C₁₂H₁₆F₄O₄
• 分子量: 300.25
• InChiKey: QMYMFKGSCSFNHK-HAQNSBGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Dimethyl trans-1,4-bis(difluoromethyl)-1,4-cyclohexanedicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以91%的产率得到trans-1,4-Bis(difluoromethyl)-1,4-cyclohexanedimethanol
  参考文献：
  名称：

  Tetramethyl 1,1,4,4-cyclohexanetetracarboxylate: preparation and conversion to key precursors of fluorinated, stereochemically defined cyclohexanes

  摘要：

  Stereoselective low-temperature diisobutylaluminum hydride (DIBALH) reduction of the title tetraester 3 affords trans-1,4-dialdehyde 4a as the major product. Fluorination of 4a,b, followed by additional elaboration leads to novel, 1,1,4,4-tetrasubstituted cyclohexanes bearing trans-1,4-difluoromethyl and fluoromethyl groups. The effect of ring size and number of ester substituents on the outcome of the reduction has been examined and treatment of dimethyl 1,1-cycloalkyl diesters 7a-c with excess DIBALH results in reduction of only one ester group. An entry into trans-1,4-trifluoromethylated tetrasubstituted cyclohexanes has been gained through stereoselective SF4 fluorination of 1,1,4,4-cyclohexanetetracarboxylic acid 17. Stereochemical assignments are supported by X-ray crystallographic data.

  DOI：

  10.1021/jo00076a055
• 作为产物：
  描述：

  1,4-环己烷二羧酸二甲酯 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 (diethylamido)sulfur trifluoride 、 二异丁基氢化铝 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 Dimethyl trans-1,4-bis(difluoromethyl)-1,4-cyclohexanedicarboxylate
  参考文献：
  名称：

  Tetramethyl 1,1,4,4-cyclohexanetetracarboxylate: preparation and conversion to key precursors of fluorinated, stereochemically defined cyclohexanes

  摘要：

  Stereoselective low-temperature diisobutylaluminum hydride (DIBALH) reduction of the title tetraester 3 affords trans-1,4-dialdehyde 4a as the major product. Fluorination of 4a,b, followed by additional elaboration leads to novel, 1,1,4,4-tetrasubstituted cyclohexanes bearing trans-1,4-difluoromethyl and fluoromethyl groups. The effect of ring size and number of ester substituents on the outcome of the reduction has been examined and treatment of dimethyl 1,1-cycloalkyl diesters 7a-c with excess DIBALH results in reduction of only one ester group. An entry into trans-1,4-trifluoromethylated tetrasubstituted cyclohexanes has been gained through stereoselective SF4 fluorination of 1,1,4,4-cyclohexanetetracarboxylic acid 17. Stereochemical assignments are supported by X-ray crystallographic data.

  DOI：

  10.1021/jo00076a055