(R,S)-1,2-dicyano-3-(2-methylbutoxy)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R,S)-1,2-dicyano-3-(2-methylbutoxy)benzene
• 英文别名: 3-(2-Methylbutoxy)benzene-1,2-dicarbonitrile；3-(2-methylbutoxy)benzene-1,2-dicarbonitrile
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: VDLLLHOGQXAUCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,S)-1,2-dicyano-3-(2-methylbutoxy)benzene 在 无水二甲氨基乙醇 作用下， 反应 6.0h， 生成 8,17,26,35-Tetrakis(2-methylbutoxy)-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3(40),4(9),5,7,10,12(39),13(18),14,16,19,21,23,25,27,30(37),31(36),32,34-nonadecaene 、 、 、
  参考文献：
  名称：

  Influence of Substituents, Reaction Conditions and Central Metals on the Isomer Distributions of 1(4)-Tetrasubstituted Phthalocyanines

  摘要：

  The 1(4)- and 2(3)-tetraalkoxy-substituted nickel (5), copper (6), and metal-free phthalocyanines 7 and 8 were synthesized from the corresponding substituted phthalonitriles 2 and 4, respectively, and the four structural isomers formed for each phthalocyanine were separated by HPLC. In the case of 1(4)-tetraalkoxy-substituted phthalocyanines the ratio of the four isomers was found to be different from the expected statistical distribution of D-2h:C-5:C-2v:C-4h = 12.5:50:25:12.5. For the 1(4)-substituted metal-fret: phthalocyanine 7 a very high proportion of the C-4h isomer (87%) is formed. In the case of the 1(4)-substituted metal phthalocyanines 5 and 6 the strikingly low proportion of the D-2h isomer (found: 2-4% compared to statistical distribution: 12.5%) is interpreted by a template mechanism (given in Scheme 2) in which strong steric hindrance of the respective neighboring groups prevent the formation of the D-2h isomer. To investigate further the mechanism of formation of phthalocyanines the synthesis of 1(4)- and 2(3)-tetraalkoxy-substituted metal phthalocyanines containing chiral alkoxy groups (13-17) was studied under different reaction conditions starting from the corresponding alkoxy-substituted phthalonitriles 10 and 11. In all investigated cases the chiral alkoxy groups in the starting phthalonitrile again affect the distribution of the structural isomers of the formed phthalocyanines, lending to a higher proportion of the C-4h isomer in comparison with the 1(4)-tetraalkoxy-substituted phthalocyanines with racemic alkoxy groups.

  DOI：

  10.1002/(sici)1521-3765(19990104)5:1<280::aid-chem280>3.0.co;2-0
• 作为产物：
  描述：

  2-甲基丁醇 、 3-硝基邻苯二腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以35%的产率得到(R,S)-1,2-dicyano-3-(2-methylbutoxy)benzene
  参考文献：
  名称：

  Influence of Substituents, Reaction Conditions and Central Metals on the Isomer Distributions of 1(4)-Tetrasubstituted Phthalocyanines

  摘要：

  The 1(4)- and 2(3)-tetraalkoxy-substituted nickel (5), copper (6), and metal-free phthalocyanines 7 and 8 were synthesized from the corresponding substituted phthalonitriles 2 and 4, respectively, and the four structural isomers formed for each phthalocyanine were separated by HPLC. In the case of 1(4)-tetraalkoxy-substituted phthalocyanines the ratio of the four isomers was found to be different from the expected statistical distribution of D-2h:C-5:C-2v:C-4h = 12.5:50:25:12.5. For the 1(4)-substituted metal-fret: phthalocyanine 7 a very high proportion of the C-4h isomer (87%) is formed. In the case of the 1(4)-substituted metal phthalocyanines 5 and 6 the strikingly low proportion of the D-2h isomer (found: 2-4% compared to statistical distribution: 12.5%) is interpreted by a template mechanism (given in Scheme 2) in which strong steric hindrance of the respective neighboring groups prevent the formation of the D-2h isomer. To investigate further the mechanism of formation of phthalocyanines the synthesis of 1(4)- and 2(3)-tetraalkoxy-substituted metal phthalocyanines containing chiral alkoxy groups (13-17) was studied under different reaction conditions starting from the corresponding alkoxy-substituted phthalonitriles 10 and 11. In all investigated cases the chiral alkoxy groups in the starting phthalonitrile again affect the distribution of the structural isomers of the formed phthalocyanines, lending to a higher proportion of the C-4h isomer in comparison with the 1(4)-tetraalkoxy-substituted phthalocyanines with racemic alkoxy groups.

  DOI：

  10.1002/(sici)1521-3765(19990104)5:1<280::aid-chem280>3.0.co;2-0

文献信息

• Influence of Substituents, Reaction Conditions and Central Metals on the Isomer Distributions of 1(4)-Tetrasubstituted Phthalocyanines
  作者：Christine Rager、Gabriele Schmid、Michael Hanack

  DOI：10.1002/(sici)1521-3765(19990104)5:1<280::aid-chem280>3.0.co;2-0

  日期：1999.1.4

  The 1(4)- and 2(3)-tetraalkoxy-substituted nickel (5), copper (6), and metal-free phthalocyanines 7 and 8 were synthesized from the corresponding substituted phthalonitriles 2 and 4, respectively, and the four structural isomers formed for each phthalocyanine were separated by HPLC. In the case of 1(4)-tetraalkoxy-substituted phthalocyanines the ratio of the four isomers was found to be different from the expected statistical distribution of D-2h:C-5:C-2v:C-4h = 12.5:50:25:12.5. For the 1(4)-substituted metal-fret: phthalocyanine 7 a very high proportion of the C-4h isomer (87%) is formed. In the case of the 1(4)-substituted metal phthalocyanines 5 and 6 the strikingly low proportion of the D-2h isomer (found: 2-4% compared to statistical distribution: 12.5%) is interpreted by a template mechanism (given in Scheme 2) in which strong steric hindrance of the respective neighboring groups prevent the formation of the D-2h isomer. To investigate further the mechanism of formation of phthalocyanines the synthesis of 1(4)- and 2(3)-tetraalkoxy-substituted metal phthalocyanines containing chiral alkoxy groups (13-17) was studied under different reaction conditions starting from the corresponding alkoxy-substituted phthalonitriles 10 and 11. In all investigated cases the chiral alkoxy groups in the starting phthalonitrile again affect the distribution of the structural isomers of the formed phthalocyanines, lending to a higher proportion of the C-4h isomer in comparison with the 1(4)-tetraalkoxy-substituted phthalocyanines with racemic alkoxy groups.