4-(p-tolylsulfonyl)phthalonitrile | 183059-88-3

• 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: 4-(p-tolylsulfonyl)phthalonitrile
• 英文别名: 2-Cyano-4-[(4-methylphenyl)sulfonyl]phenyl cyanide；4-(4-methylphenyl)sulfonylbenzene-1,2-dicarbonitrile
• CAS: 183059-88-3
• 化学式: C₁₅H₁₀N₂O₂S
• 分子量: 282.323
• InChiKey: IWCOOVHIDUMCAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(p-tolylsulfonyl)phthalonitrile 在 氨 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到3-Imino-6-(toluene-4-sulfonyl)-3H-isoindol-1-ylamine
  参考文献：
  名称：

  Synthesis of Novel Unsymmetrically Substituted Push-Pull Phthalocyanines

  摘要：

  The synthesis and characterization of novel non-centrosymmetrically push-pull substituted metal-free phthalocyanines 3-9 are described. The compounds have different donor (dialkoxy, tert-butyl, methyl, p-tolylthio) and/or attractor (p-tolylsulfinyl, p-tolylsulfonyl, nitro) functional groups, are soluble in organic solvents, and are especially designed to study their second- and third-order nonlinear optical properties. Compounds 7-9 are mixtures of the four corresponding regioisomers. For preparing the unsymmetrical phthalocyanines 7-9, the effectiveness of the subphthalocyanine route, using different substituted diiminoisoindolines as reagents, has been tested. Furthermore, a comparison between this method versus the statistical one has been done. The results obtained show that the ring enlargement reaction of subphthalocyanines to obtain unsymmetrically substituted phthalocyanines is not a selective reaction but a multistep process, which depends dramatically on the nature of the substituents on the subphthalocyanines, the reactivity of the iminoisoindoline, the solvent, and other factors that limit its general synthetic utility. Preliminary data of the experimental second-order hyperpolarizabilities of compounds 3-9 are also given.

  DOI：

  10.1021/jo961018o
• 作为产物：
  描述：

  4-硝基邻苯二甲腈 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 42.0h， 生成 4-(p-tolylsulfonyl)phthalonitrile
  参考文献：
  名称：

  Synthesis of Novel Unsymmetrically Substituted Push-Pull Phthalocyanines

  摘要：

  The synthesis and characterization of novel non-centrosymmetrically push-pull substituted metal-free phthalocyanines 3-9 are described. The compounds have different donor (dialkoxy, tert-butyl, methyl, p-tolylthio) and/or attractor (p-tolylsulfinyl, p-tolylsulfonyl, nitro) functional groups, are soluble in organic solvents, and are especially designed to study their second- and third-order nonlinear optical properties. Compounds 7-9 are mixtures of the four corresponding regioisomers. For preparing the unsymmetrical phthalocyanines 7-9, the effectiveness of the subphthalocyanine route, using different substituted diiminoisoindolines as reagents, has been tested. Furthermore, a comparison between this method versus the statistical one has been done. The results obtained show that the ring enlargement reaction of subphthalocyanines to obtain unsymmetrically substituted phthalocyanines is not a selective reaction but a multistep process, which depends dramatically on the nature of the substituents on the subphthalocyanines, the reactivity of the iminoisoindoline, the solvent, and other factors that limit its general synthetic utility. Preliminary data of the experimental second-order hyperpolarizabilities of compounds 3-9 are also given.

  DOI：

  10.1021/jo961018o

文献信息

• A diastereoselective process induced in a curved aromatic molecule: oxidation of thioether-substituted subphthalocyanines
  作者：David González-Rodríguez、Tomás Torres

  DOI：10.1016/j.tetlet.2008.11.126

  日期：2009.2

  Different sulfoxide-substituted subphthalocyanines have been synthesized by oxidation reaction of the corresponding thioether precursors. We have observed for the first time that when the oxidation takes place close to the macrocyclic core, the intrinsically chiral subphthalocyanine can induce a high degree of diastereoselectivity in this process. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Novel Unsymmetrically Substituted Push-Pull Phthalocyanines
  作者：Ángela Sastre、Belén del Rey、Tomás Torres

  DOI：10.1021/jo961018o

  日期：1996.1.1

  The synthesis and characterization of novel non-centrosymmetrically push-pull substituted metal-free phthalocyanines 3-9 are described. The compounds have different donor (dialkoxy, tert-butyl, methyl, p-tolylthio) and/or attractor (p-tolylsulfinyl, p-tolylsulfonyl, nitro) functional groups, are soluble in organic solvents, and are especially designed to study their second- and third-order nonlinear optical properties. Compounds 7-9 are mixtures of the four corresponding regioisomers. For preparing the unsymmetrical phthalocyanines 7-9, the effectiveness of the subphthalocyanine route, using different substituted diiminoisoindolines as reagents, has been tested. Furthermore, a comparison between this method versus the statistical one has been done. The results obtained show that the ring enlargement reaction of subphthalocyanines to obtain unsymmetrically substituted phthalocyanines is not a selective reaction but a multistep process, which depends dramatically on the nature of the substituents on the subphthalocyanines, the reactivity of the iminoisoindoline, the solvent, and other factors that limit its general synthetic utility. Preliminary data of the experimental second-order hyperpolarizabilities of compounds 3-9 are also given.