diethyl 5,5'-bisbiphenyl-3,3'-dicarboxylate | 220961-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl 5,5'-bisbiphenyl-3,3'-dicarboxylate
• CAS: 220961-67-1
• 化学式: C₅₀H₄₈N₂O₁₂S₂
• 分子量: 933.069
• InChiKey: DIOSVAJFXUMGDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.38
• 重原子数：
  66.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  179.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  diethyl 5,5'-bisbiphenyl-3,3'-dicarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 8.0h， 以94%的产率得到diethyl 5,5'-bis<(4-tolylsulfonylamino)methyl>biphenyl-3,3'-dicarboxylate
  参考文献：
  名称：

  Broad Molecular Ribbons of Nanometer Size Composed of Biphenyl Units

  摘要：

  The new tetrafunctionalized biphenyl key building blocks 16 and 39 led, for the first time, to the hitherto broadest molecular ribbons that contain biphenyl units in a transverse arrangement by iterative synthetic methods. The length and breadth of the molecular ribbons, as single chemical entities, are diversified. They can be used as cyclization precursors in the synthesis of long molecular tubes of type 2 with a large diameter. The solubility and the host-guest behavior (clathrate formation with benzene, dimethylformamide, and dichloromethane) of these nanometer-size molecular ribbons were optimized by the introduction of various side chains (benzenesulfonamide, 4-toluenesulfonamide, and 4-terf-butylbenzenesulfonamide groups) into the skeleton of the ribbons. New 14-, 15-, and 16-membered model ring systems (compounds 20a, 22a, and 24 respectively) were synthesized in order to examine the constitution of the 16-membered diaza[3.3]-phane 18a. Nanometer-size tube-shaped molecules 7a, 7b and 8 were obtained by cyclization of tetrafunctionalized molecular ribbons with the biphenyl building block. The constitution and conformation of the molecular ribbons and belts were proven by NOE experiments and X-ray analyses.

  DOI：

  10.1002/(sici)1521-3765(19990104)5:1<345::aid-chem345>3.0.co;2-t
• 作为产物：
  描述：

  ethyl 3-(3-ethoxycarbonyl-5-methylphenyl)-5-methylbenzoate 在 N-溴代丁二酰亚胺(NBS) 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 diethyl 5,5'-bisbiphenyl-3,3'-dicarboxylate
  参考文献：
  名称：

  Broad Molecular Ribbons of Nanometer Size Composed of Biphenyl Units

  摘要：

  The new tetrafunctionalized biphenyl key building blocks 16 and 39 led, for the first time, to the hitherto broadest molecular ribbons that contain biphenyl units in a transverse arrangement by iterative synthetic methods. The length and breadth of the molecular ribbons, as single chemical entities, are diversified. They can be used as cyclization precursors in the synthesis of long molecular tubes of type 2 with a large diameter. The solubility and the host-guest behavior (clathrate formation with benzene, dimethylformamide, and dichloromethane) of these nanometer-size molecular ribbons were optimized by the introduction of various side chains (benzenesulfonamide, 4-toluenesulfonamide, and 4-terf-butylbenzenesulfonamide groups) into the skeleton of the ribbons. New 14-, 15-, and 16-membered model ring systems (compounds 20a, 22a, and 24 respectively) were synthesized in order to examine the constitution of the 16-membered diaza[3.3]-phane 18a. Nanometer-size tube-shaped molecules 7a, 7b and 8 were obtained by cyclization of tetrafunctionalized molecular ribbons with the biphenyl building block. The constitution and conformation of the molecular ribbons and belts were proven by NOE experiments and X-ray analyses.

  DOI：

  10.1002/(sici)1521-3765(19990104)5:1<345::aid-chem345>3.0.co;2-t