methyl 5-ethynyl-2-{4-[4-(tert-butoxycarbonylamino)phenylethynyl]-3-(methoxycarbonyl)phenylethynyl}benzoate | 879413-48-6

• 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: methyl 5-ethynyl-2-{4-[4-(tert-butoxycarbonylamino)phenylethynyl]-3-(methoxycarbonyl)phenylethynyl}benzoate
• 英文别名: Methyl 5-ethynyl-2-[2-[3-methoxycarbonyl-4-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethynyl]phenyl]ethynyl]benzoate；methyl 5-ethynyl-2-[2-[3-methoxycarbonyl-4-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethynyl]phenyl]ethynyl]benzoate
• CAS: 879413-48-6
• 化学式: C₃₃H₂₇NO₆
• 分子量: 533.58
• InChiKey: MWGPLSUCXPGOBN-UHFFFAOYSA-N

物化性质

• 沸点：
  665.1±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-ethynyl-2-{4-[4-(tert-butoxycarbonylamino)phenylethynyl]-3-(methoxycarbonyl)phenylethynyl}benzoate 、 1,8-diiodo-10-methoxyanthracene 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以27%的产率得到1,8-bis(4-{4-[4-(tert-butoxycarbonylamino)phenylethynyl]-3-[methoxycarbonyl]phenylethynyl}-3-{methoxycarbonyl}phenylethynyl)-10-methoxyanthracene
  参考文献：
  名称：

  Synthesis and Optical Properties of Bis(oligophenyleneethynylenes)

  摘要：

  Bis(oligophenyleneethynylenes) 1-4 were prepared as representative members of a new class of potential nonlinear optical materials. The optical properties of 1-4 were examined for evidence of restricted rotation of the aryl rings when compared to their single-strand precursors, which could potentially increase their nonlinear response through more effective conjugation. The effect of altering the electron density of the terminating functional group of these compounds on their properties was also investigated.

  DOI：

  10.1021/jo052242t
• 作为产物：
  描述：

  methyl 2-iodo-5-(trimethylsilylethynyl)benzoate 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 methyl 5-ethynyl-2-{4-[4-(tert-butoxycarbonylamino)phenylethynyl]-3-(methoxycarbonyl)phenylethynyl}benzoate
  参考文献：
  名称：

  The synthesis of bis(oligophenyleneethynylenes): novel potential nonlinear optical materials

  摘要：

  Various functionalised phenyleneethynylene dimers 10 and trimers 12 were synthesised by palladium-catalyzed Sonogashira methodology. These dimers and trimers were coupled to 1,8-diido-10-methoxyanthracene to generate bis(oligophenyleneethynylenes) 17 and 18. Preliminary results towards the construction of both phenyleneethynylene and phenylenevinylene hybrid motifs are presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.015

文献信息

• The synthesis of bis(oligophenyleneethynylenes): novel potential nonlinear optical materials
  作者：David J. Armitt、Geoffrey T. Crisp

  DOI：10.1016/j.tet.2005.11.015

  日期：2006.2

  Various functionalised phenyleneethynylene dimers 10 and trimers 12 were synthesised by palladium-catalyzed Sonogashira methodology. These dimers and trimers were coupled to 1,8-diido-10-methoxyanthracene to generate bis(oligophenyleneethynylenes) 17 and 18. Preliminary results towards the construction of both phenyleneethynylene and phenylenevinylene hybrid motifs are presented. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Optical Properties of Bis(oligophenyleneethynylenes)
  作者：David J. Armitt、Geoffrey T. Crisp

  DOI：10.1021/jo052242t

  日期：2006.4.1

  Bis(oligophenyleneethynylenes) 1-4 were prepared as representative members of a new class of potential nonlinear optical materials. The optical properties of 1-4 were examined for evidence of restricted rotation of the aryl rings when compared to their single-strand precursors, which could potentially increase their nonlinear response through more effective conjugation. The effect of altering the electron density of the terminating functional group of these compounds on their properties was also investigated.