(R,S)-1,2-dicyano-3-(2-ethylhexyloxy)benzene | 130107-88-9

• 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-ethylhexyloxy)benzene
• 英文别名: 1,2-dicyano-3-(2-ethylhexyloxy)benzene；dicyano-3-(2-ethyl-hexyloxy)benzene；1,2-Benzenedicarbonitrile, 3-[(2-ethylhexyl)oxy]-；3-(2-ethylhexoxy)benzene-1,2-dicarbonitrile
• CAS: 130107-88-9
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: KXCJTHFYKNTDHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-ethylhexyloxy)benzene 在 2-乙基-1-己酸锂 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 生成 5,14,23,32-Tetrakis(2-ethylhexoxy)-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-1,3,5,7,9,11,13(18),14,16,19(39),20,22(27),23,25,28,30(37),31(36),32,34-nonadecaene 、 5,14,26,35-Tetrakis(2-ethylhexoxy)-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-1,3,5,7,9,11,13(18),14,16,19(39),20,22(27),23,25,28,30(37),31(36),32,34-nonadecaene 、 5,14,26,32-Tetrakis(2-ethylhexoxy)-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-1,3,5,7,9,11,13(18),14,16,19(39),20,22(27),23,25,28,30(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-乙基己醇 、 3-硝基邻苯二腈 在 sodium hydride 作用下， 以 N-甲基吡咯烷酮 、 mineral oil 为溶剂， 以91%的产率得到(R,S)-1,2-dicyano-3-(2-ethylhexyloxy)benzene
  参考文献：
  名称：

  Verfahren zur Herstellung von 3-Alkoxyphthalsäuredinitrilen

  摘要：

  制备3-烷氧基邻苯二腈的方法，化学式为I，其中R代表可能被取代的烷基或环烷基，通过将3-硝基邻苯二腈与醇ROH在与反应物不同的溶剂中，在碱的存在下反应，其特征在于要么a) 3-硝基邻苯二腈和碱在一个溶剂中预先混合，然后加入醇ROH；要么b) 醇ROH和碱在一个溶剂中预先混合，然后加入3-硝基邻苯二腈。

  公开号：

  EP1424323A1

文献信息

• Verfahren zur Herstellung von 3-Alkoxyphthalsäuredinitrilen
  申请人：Bayer Chemicals AG

  公开号：EP1424323A1

  公开（公告）日：2004-06-02

  Verfahren zur Herstellung von 3-Alkoxyphthalsäuredinitrilen der Formel I worin Rfür gegebenenfalls substituiertes Alkyl oder Cycloalkyl steht, durch Umsetzung von 3-Nitrophthalsäuredinitril mit einem Alkohol ROH, in einem von den Reaktanden verschiedenen Lösungsmittel in Gegenwart einer Base, dadurch gekennzeichnet, dass entweder a) 3-Nitrophthalsäuredinitril und die Base in einem Lösungsmittel vorgelegt werden und der Alkohol ROH der Vorlage zugegeben wird, oder b) der Alkohol ROH und die Base in einem Lösungsmittel vorgelegt werden und 3-Nitrophthalsäuredinitril der Vorlage zugegeben wird.

  制备3-烷氧基邻苯二腈的方法，化学式为I，其中R代表可能被取代的烷基或环烷基，通过将3-硝基邻苯二腈与醇ROH在与反应物不同的溶剂中，在碱的存在下反应，其特征在于要么a) 3-硝基邻苯二腈和碱在一个溶剂中预先混合，然后加入醇ROH；要么b) 醇ROH和碱在一个溶剂中预先混合，然后加入3-硝基邻苯二腈。
• [DE] VERFAHREN ZUR HERSTELLUNG VON ALKOXYSUBSTITUIERTEN PHTHALOCYANINEN<br/>[EN] METHOD FOR PRODUCING ALKOXY-SUBSTITUTED PHTHALOCYANINS<br/>[FR] PROCEDE POUR PRODUIRE DES PHTALOCYANINES SUBSTITUEES PAR ALCOXY
  申请人：BAYER CHEMICALS AG

  公开号：WO2005003133A3

  公开（公告）日：2005-02-24
• Hanack, Michael; Schmid, Gabriele; Sommerauer, Michael, Angewandte Chemie, 1993, vol. 105, p. 1540 - 1542
  作者：Hanack, Michael、Schmid, Gabriele、Sommerauer, Michael

  DOI：——

  日期：——
• VERFAHREN ZUR HERSTELLUNG VON ALKOXYSUBSTITUIERTEN PHTHALOCYANINEN
  申请人：LANXESS Deutschland GmbH

  公开号：EP1644378A2

  公开（公告）日：2006-04-12
• Method for producing alkoxy-substituted phthalocyanins
  申请人：Berneth Horst

  公开号：US20070179285A1

  公开（公告）日：2007-08-02

  The invention relates to a process for preparing alkoxy-substituted, metal-containing phthalocyanines of the formula (I) where R is substituted or unsubstituted alkyl or cycloalkyl, M is a divalent metal atom, metaloxy or a trivalent or tetravalent substituted metal atom, characterized in that the phthalonitrile of the formula (II) is reacted in the presence of a metal salt and a base in a water-miscible solvent.