Dimethyl 1,4-diformyl-1,4-cyclohexanedicarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Dimethyl 1,4-diformyl-1,4-cyclohexanedicarboxylate
• 英文别名: Dimethyl 1,4-diformylcyclohexane-1,4-dicarboxylate
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: ADSDQMNLFDXCEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dimethyl 1,4-diformyl-1,4-cyclohexanedicarboxylate 在 lithium aluminium tetrahydride 、 草酰氯 、 (diethylamido)sulfur trifluoride 、 二甲基亚砜 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 18.33h， 生成 trans-1,4-Bis(difluoromethyl)-1,4-cyclohexanedicarboxaldehyde
  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：

  Trimethyl 1,1,4-cyclohexanetricarboxylate 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 Dimethyl 1,4-diformyl-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

文献信息

• Molecular Gyroscope with a <i>trans</i>-Cyclohexane-1,4-diimine Rotor Unit: Isolation and Characterization of a Geometric Isomer as a Formal Intermediate of Hindered Rotation
  作者：Hiroyoshi Sugino、Hidetoshi Kawai、Kenshu Fujiwara、Takanori Suzuki

  DOI：10.1246/cl.2012.79

  日期：2012.1.5

  Condensation reactions of macrocyclic diamines 1 and cyclohexane-1,4-dicarbaldehydes 2 with the substituents at 1,4-positions gave a series of macrocage molecules that can be considered molecular g...

  大环二胺 1 和环己烷-1,4-二甲醛 2 与 1,4-位取代基的缩合反应得到了一系列可被认为是分子 g...