16,18-Dimethyl-3,13-dithiatricyclo[13.3.1.16,10]icosa-1(18),6(20),7,9,15-pentaene-17,19-dione | 475110-50-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 16,18-Dimethyl-3,13-dithiatricyclo[13.3.1.16,10]icosa-1(18),6(20),7,9,15-pentaene-17,19-dione
• 英文别名: 16,18-dimethyl-3,13-dithiatricyclo[13.3.1.16,10]icosa-1(18),6(20),7,9,15-pentaene-17,19-dione
• CAS: 475110-50-0
• 化学式: C₂₀H₂₂O₂S₂
• 分子量: 358.525
• InChiKey: BXLYNSSDVNLHOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  16,18-Dimethyl-3,13-dithiatricyclo[13.3.1.16,10]icosa-1(18),6(20),7,9,15-pentaene-17,19-dione 在 sodium dithionite 作用下， 以 水 、 乙酸乙酯 为溶剂， 以70%的产率得到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 、 三乙胺 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 22.0h， 生成 16,18-Dimethyl-3,13-dithiatricyclo[13.3.1.16,10]icosa-1(18),6(20),7,9,15-pentaene-17,19-dione
  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