2,6-bis(chloromethyl)-3,5-dimethyl-1,4-benzoquinone | 475110-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis(chloromethyl)-3,5-dimethyl-1,4-benzoquinone
• 英文别名: 2,6-Bis(chloromethyl)-3,5-dimethyl-2,5-cyclohexadiene-1,4-dione；2,6-bis(chloromethyl)-3,5-dimethylcyclohexa-2,5-diene-1,4-dione
• CAS: 475110-49-7
• 化学式: C₁₀H₁₀Cl₂O₂
• 分子量: 233.094
• InChiKey: RBHNCAHKXQEOPE-UHFFFAOYSA-N

物化性质

• 沸点：
  299.4±35.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-bis(chloromethyl)-3,5-dimethyl-1,4-benzoquinone 在 sodium dithionite 、 三乙胺 作用下， 以 水 、 乙酸乙酯 、 苯 为溶剂， 反应 10.0h， 生成 16,18-Dimethyl-3,13-dithiatricyclo[13.3.1.16,10]icosa-1(18),6(20),7,9,15(19),16-hexaene-17,19-diol
  参考文献：
  名称：

  An Electrochemically Controllable Nanomechanical Molecular System Utilizing Edge-to-Face and Face-to-Face Aromatic Interactions

  摘要：

  [GRAPHICS]A new molecular system, 2,11-dithio[4,4]metametaquinocyclophane containing a quinone moiety; was designed and synthesized. As the quinone moiety can readily be converted into an aromatic pi-system (hydroquinone) upon reduction, the nanomechanical molecular cyclophane system exhibits a large flapping motion like a molecular flipper from the electrochemical redox process. The conformational changes upon reduction and oxidation are caused by changes of nonbonding interaction forces (devoid of bond formation/breaking) from the edge-to-face to face-to-face aromatic interactions and vice versa, respectively.

  DOI：

  10.1021/ol0268541
• 作为产物：
  描述：

  3,5-dichloromethyl-2,6-dimethylhydroquinone dimethyl ether 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以66%的产率得到2,6-bis(chloromethyl)-3,5-dimethyl-1,4-benzoquinone
  参考文献：
  名称：

  An Electrochemically Controllable Nanomechanical Molecular System Utilizing Edge-to-Face and Face-to-Face Aromatic Interactions

  摘要：

  [GRAPHICS]A new molecular system, 2,11-dithio[4,4]metametaquinocyclophane containing a quinone moiety; was designed and synthesized. As the quinone moiety can readily be converted into an aromatic pi-system (hydroquinone) upon reduction, the nanomechanical molecular cyclophane system exhibits a large flapping motion like a molecular flipper from the electrochemical redox process. The conformational changes upon reduction and oxidation are caused by changes of nonbonding interaction forces (devoid of bond formation/breaking) from the edge-to-face to face-to-face aromatic interactions and vice versa, respectively.

  DOI：

  10.1021/ol0268541