Dimethyl 1,2,3,4-tetrakis[(trimethylsilyl)ethynyl]phthalate

• 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: Dimethyl 1,2,3,4-tetrakis[(trimethylsilyl)ethynyl]phthalate
• 英文别名: Dimethyl 3,4,5,6-tetrakis(2-trimethylsilylethynyl)benzene-1,2-dicarboxylate
• 化学式: C₃₀H₄₂O₄Si₄
• 分子量: 579.003
• InChiKey: GISYLYRNDZTZBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl 1,2,3,4-tetrakis[(trimethylsilyl)ethynyl]phthalate 在 potassium fluoride 、 18-冠醚-6 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.5h， 生成 3,4,5,6-Tetraethynyl-phthalic acid dimethyl ester
  参考文献：
  名称：

  On the Nature of Nonplanarity in the [N]Phenylenes

  摘要：

  The [N]phenylenes display marked deformation from planarity in the crystalline state. In order to probe the generality of this phenomenon, several derivatives were synthesized and their single-crystal X-ray structures were obtained. All new compounds displayed some degree of nonplanarity. Thus, for example, the parent triangular [4]phenylene (4b) has a median bend angle at the ring junction of 1.5 degrees and a range of 0.3 degrees to 3.5 degrees, whereas hexakis[triisopropylsilyl(ethynyl)] triangular [4]phenylene (4c) possesses the bulkiest appendages and the largest median bend angle and range (3.8 degrees and 1.7 degrees-5.6 degrees, respectively). A detailed analysis of the bending and twisting angles at the ring junctions, however, revealed that the magnitude of deformations were independent of topology, molecular size, and substituent type. In contrast to the phenylenes, a Cambridge Structural Database (CSD) search of unsubstituted and non-peri-substituted naphthalenes and anthracenes shows these molecules to be virtually planar in the solid state. A comparison of the single-point energies (HF/6-31G*) of the phenylenes with the acenes calculated for molecules possessing a fixed bend angle at the ring fusion of 3 degrees, 6 degrees, 9 degrees, and 12 degrees reveals the former to be 26% to 45% easier to deform than the latter. Based on these results, the nonplanarity seen for the phenylenes is most likely a consequence of crystal-packing forces deforming particularly flexible molecules.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3399::aid-chem3399>3.0.co;2-v
• 作为产物：
  描述：

  四溴苯酐二甲酯 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 反应 72.0h， 以33%的产率得到Dimethyl 1,2,3,4-tetrakis[(trimethylsilyl)ethynyl]phthalate
  参考文献：
  名称：

  On the Nature of Nonplanarity in the [N]Phenylenes

  摘要：

  The [N]phenylenes display marked deformation from planarity in the crystalline state. In order to probe the generality of this phenomenon, several derivatives were synthesized and their single-crystal X-ray structures were obtained. All new compounds displayed some degree of nonplanarity. Thus, for example, the parent triangular [4]phenylene (4b) has a median bend angle at the ring junction of 1.5 degrees and a range of 0.3 degrees to 3.5 degrees, whereas hexakis[triisopropylsilyl(ethynyl)] triangular [4]phenylene (4c) possesses the bulkiest appendages and the largest median bend angle and range (3.8 degrees and 1.7 degrees-5.6 degrees, respectively). A detailed analysis of the bending and twisting angles at the ring junctions, however, revealed that the magnitude of deformations were independent of topology, molecular size, and substituent type. In contrast to the phenylenes, a Cambridge Structural Database (CSD) search of unsubstituted and non-peri-substituted naphthalenes and anthracenes shows these molecules to be virtually planar in the solid state. A comparison of the single-point energies (HF/6-31G*) of the phenylenes with the acenes calculated for molecules possessing a fixed bend angle at the ring fusion of 3 degrees, 6 degrees, 9 degrees, and 12 degrees reveals the former to be 26% to 45% easier to deform than the latter. Based on these results, the nonplanarity seen for the phenylenes is most likely a consequence of crystal-packing forces deforming particularly flexible molecules.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3399::aid-chem3399>3.0.co;2-v