trans-1,4-Bis(difluoromethyl)-1,4-bis(fluoromethyl)cyclohexane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: trans-1,4-Bis(difluoromethyl)-1,4-bis(fluoromethyl)cyclohexane
• 化学式: C₁₀H₁₄F₆
• 分子量: 248.212
• InChiKey: BHDLVINIZKRQCM-MGCOHNPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  Trimethyl 1,1,4-cyclohexanetricarboxylate 在 吡啶 、 2,2,6,6-四甲基哌啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 (diethylamido)sulfur trifluoride 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 trans-1,4-Bis(difluoromethyl)-1,4-bis(fluoromethyl)cyclohexane
  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

文献信息

• Tetramethyl 1,1,4,4-cyclohexanetetracarboxylate: preparation and conversion to key precursors of fluorinated, stereochemically defined cyclohexanes
  作者：Charles R. Davis、Dale C. Swenson、Donald J. Burton

  DOI：10.1021/jo00076a055

  日期：1993.11

  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.