3-[(methyloxycarbonyl)phenoxy]phthalonitrile | 947507-13-3

• 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: 3-[(methyloxycarbonyl)phenoxy]phthalonitrile
• 英文别名: Methyl 2-(2,3-dicyanophenoxy)benzoate
• CAS: 947507-13-3
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: VNSCQPBMVJZPHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  戊醇 、 3-[(methyloxycarbonyl)phenoxy]phthalonitrile 在 zinc(II) acetate dihydrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以6%的产率得到
  参考文献：
  名称：

  Synthesis and separation of the constitutional isomers of 1(4),8(11),15(18),22(25)-tetrakis[(pentyloxycarbonyl)phenoxy]-phthalocyaninato zinc(II) complexes

  摘要：

  Cyclic tetramerization of 3-[(methyloxycarbonyl)phenoxy]phthalonitrile (1a-1c) in the presence of Zn(OAc)(2)center dot 2H(2)O and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) followed by transesterification in refluxing n-pentanol afforded 1(4),8(11),15(18),22(25)-tetrakis[(pentyloxycarbonyl)phenoxy]phthalocyaninato zinc(II) complexes (2a-2c) as a mixture of four constitutional isomers. Simple silica-gel column chromatography leads to the successful separation of pure isomers with the C-4h and D-2h symmetry together with a section containing the C-2v and C-s isomers, which have been characterized with a wide range of spectroscopic methods including MALDI-TOF mass, electronic absorption, H-1 NMR, and 2D COSY spectroscopy. Synthesis yields in combination with the NMR spectroscopic results reveal that the distribution of the four isomers in the final product for 2a-2c does not strictly follow that expected according to statistical calculation with the ratio of C-4h:C-2v:C-s:D-2h = 1:2:4:1, indicating the effect of steric hindrance of substituents on the formation of various constitutional isomers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.01.016
• 作为产物：
  描述：

  3-硝基邻苯二腈 、 水杨酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到3-[(methyloxycarbonyl)phenoxy]phthalonitrile
  参考文献：
  名称：

  Synthesis and separation of the constitutional isomers of 1(4),8(11),15(18),22(25)-tetrakis[(pentyloxycarbonyl)phenoxy]-phthalocyaninato zinc(II) complexes

  摘要：

  Cyclic tetramerization of 3-[(methyloxycarbonyl)phenoxy]phthalonitrile (1a-1c) in the presence of Zn(OAc)(2)center dot 2H(2)O and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) followed by transesterification in refluxing n-pentanol afforded 1(4),8(11),15(18),22(25)-tetrakis[(pentyloxycarbonyl)phenoxy]phthalocyaninato zinc(II) complexes (2a-2c) as a mixture of four constitutional isomers. Simple silica-gel column chromatography leads to the successful separation of pure isomers with the C-4h and D-2h symmetry together with a section containing the C-2v and C-s isomers, which have been characterized with a wide range of spectroscopic methods including MALDI-TOF mass, electronic absorption, H-1 NMR, and 2D COSY spectroscopy. Synthesis yields in combination with the NMR spectroscopic results reveal that the distribution of the four isomers in the final product for 2a-2c does not strictly follow that expected according to statistical calculation with the ratio of C-4h:C-2v:C-s:D-2h = 1:2:4:1, indicating the effect of steric hindrance of substituents on the formation of various constitutional isomers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.01.016