3-imino-5-(4-methylphenyl)sulfanylisoindol-1-amine | 183059-89-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-imino-5-(4-methylphenyl)sulfanylisoindol-1-amine
• CAS: 183059-89-4
• 化学式: C₁₅H₁₃N₃S
• 分子量: 267.354
• InChiKey: NZEFSFSLZHMVRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-imino-5-(4-methylphenyl)sulfanylisoindol-1-amine 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以11%的产率得到2-(tolylthio)phthalocyanine
  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 氨 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 3-imino-5-(4-methylphenyl)sulfanylisoindol-1-amine
  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

• Synthesis of 4-methylthiophenyl silicon phthalocyanines axially substituted with carboxylic acids for MOF materials
  作者：Víctor Sobrino-Bastán、Luis Martín-Gomis、Ángela Sastre-Santos

  DOI：10.1142/s1088424622500961

  日期：2023.1

  Two new peripherally substituted with 4 and 8 electron-donating 4-methylthiophenyl silicon phthalocyanines, [Formula: see text] 1 and [Formula: see text] 2, axially substituted with carboxylic acids have been synthesized using microwave irradiation in a very good yield. The new compounds have been characterized by ¹H-NMR, UV-vis, fluorescence, differential pulse voltammograms, and HR-MALDI-TOF mass spectrometry. An study of the stability of the axial chlorinated SiPcs in the function of the number of thiophenyl substituents indicates than [Formula: see text] 10 degradates faster, to its corresponding unreactive dihydrosilicon phthalocyanine derivative [Formula: see text] 11, than [Formula: see text]. The new SiPcs are excellent candidates as photoactive linkers for the construction of MOF materials.

  利用微波辐照合成了两种新的外围被 4 个和 8 个电子供体取代的 4-甲基噻吩基硅酞菁，[式：见正文]1 和[式：见正文]2，轴向被羧酸取代，收率非常高。新化合物通过 1H-NMR、UV-vis、荧光、微分脉冲伏安图和 HR-MALDI-TOF 质谱进行了表征。对轴向氯化 SiPcs 的稳定性与噻吩取代基数目关系的研究表明，[式：见正文] 10 比[式：见正文]更快降解为相应的无反应二氢硅酞菁衍生物[式：见正文]11。新的 SiPcs 是构建 MOF 材料的光活性连接体的极佳候选材料。
• 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.