4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile | 175883-84-8

• 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: 4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile
• 英文别名: 1,2-Benzenedicarbonitrile, 4,5-bis(3,3-dimethyl-1-butynyl)-；4,5-bis(3,3-dimethylbut-1-ynyl)benzene-1,2-dicarbonitrile
• CAS: 175883-84-8
• 化学式: C₂₀H₂₀N₂
• 分子量: 288.392
• InChiKey: LGGNDTYLNMRNDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile 在 lithium amylate 作用下， 以 戊醇 为溶剂， 反应 3.0h， 以36%的产率得到2,3,9,10,16,17,23,24-octakis(3,3-dimethyl-1-butynyl)phthalocyanine
  参考文献：
  名称：

  Synthesis of 2,3,9,10,16,17,23,24-Octaalkynylphthalocyanines and the Effects of Concentration and Temperature on Their ¹H NMR Spectra

  摘要：

  The syntheses of 3,4- and 4,5-diiodophthalonitriles are described. Coupling of the latter compound with Pd(PPh(3))(2)Cl-2 and 1-octyne, 1-heptyne, 1-hexyne, 1-pentyne, and 3,3-dimethyl-1-butyne gave a series of 4,5-dialkynylphthalonitriles. Hydrogenation of 4,5-bis(1-pentynyl)phthalonitrile and 4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile gave 4,5-dipentylphthalonitrile and 4,5-bis(3,3-dimethylbutyl)phthalonitriles. Condensation of the dialkynylphthalonitriles with lithium 1-pentoxide in 1-pentanol gave 2,3,9,10,16,17,23,24-octaalkynylphthalocyanines, while intervention of the intermediate dilithium phthalocyanines with zinc acetate gave the related zinc(II) phthalocyanines. H-1 NMR spectroscopy of these octaalkynylphthalocyanines exhibited large chemical shifts (1-2 ppm) of the internal and aromatic protons at concentrations ranging from 10(-2) to 10(-5) M and at temperatures from 27 to 147 degrees C. The effects of aggregation phenomena are discussed. The importance of reporting concentration and temperature values for NMR spectra of phthalocyanines is stressed.

  DOI：

  10.1021/jo9521662
• 作为产物：
  描述：

  4,5-diiodophthalimide 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 copper(l) iodide 、 三乙胺 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.62h， 生成 4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile
  参考文献：
  名称：

  Synthesis of 2,3,9,10,16,17,23,24-Octaalkynylphthalocyanines and the Effects of Concentration and Temperature on Their ¹H NMR Spectra

  摘要：

  The syntheses of 3,4- and 4,5-diiodophthalonitriles are described. Coupling of the latter compound with Pd(PPh(3))(2)Cl-2 and 1-octyne, 1-heptyne, 1-hexyne, 1-pentyne, and 3,3-dimethyl-1-butyne gave a series of 4,5-dialkynylphthalonitriles. Hydrogenation of 4,5-bis(1-pentynyl)phthalonitrile and 4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile gave 4,5-dipentylphthalonitrile and 4,5-bis(3,3-dimethylbutyl)phthalonitriles. Condensation of the dialkynylphthalonitriles with lithium 1-pentoxide in 1-pentanol gave 2,3,9,10,16,17,23,24-octaalkynylphthalocyanines, while intervention of the intermediate dilithium phthalocyanines with zinc acetate gave the related zinc(II) phthalocyanines. H-1 NMR spectroscopy of these octaalkynylphthalocyanines exhibited large chemical shifts (1-2 ppm) of the internal and aromatic protons at concentrations ranging from 10(-2) to 10(-5) M and at temperatures from 27 to 147 degrees C. The effects of aggregation phenomena are discussed. The importance of reporting concentration and temperature values for NMR spectra of phthalocyanines is stressed.

  DOI：

  10.1021/jo9521662

文献信息

• "Adjacent" Substituted Phthalocyanines
  作者：K. Nolan、M. Hu、C. Leznoff

  DOI：10.1055/s-1997-3226

  日期：1997.5

  2,3,9,10-Tetrakis(3,3-dimethyl-1-butynyl)phthalocyanine and 2,3,9,10-tetramethoxyphthalocyanine were prepared by the condensation of a "half" phthalocyanine intermediate (prepared from 4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile or phthalonitrile) with phthalonitrile and 4,5-dimethoxyphthalonitrile respectively.

  2,3,9,10-四(3,3-二甲基-1-丁炔基)酞菁和 2,3,9,10-四甲氧基酞菁分别是通过 "半 "酞菁中间体（由 4,5-双(3,3-二甲基-1-丁炔基)酞腈或酞腈制备）与酞腈和 4,5-二甲氧基酞腈缩合而制备的。
• Synthesis of 2,3,9,10,16,17,23,24-Octaalkynylphthalocyanines and the Effects of Concentration and Temperature on Their ¹H NMR Spectra
  作者：Dmitri S. Terekhov、Kieran J. M. Nolan、Colin R. McArthur、Clifford C. Leznoff

  DOI：10.1021/jo9521662

  日期：1996.1.1

  The syntheses of 3,4- and 4,5-diiodophthalonitriles are described. Coupling of the latter compound with Pd(PPh(3))(2)Cl-2 and 1-octyne, 1-heptyne, 1-hexyne, 1-pentyne, and 3,3-dimethyl-1-butyne gave a series of 4,5-dialkynylphthalonitriles. Hydrogenation of 4,5-bis(1-pentynyl)phthalonitrile and 4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile gave 4,5-dipentylphthalonitrile and 4,5-bis(3,3-dimethylbutyl)phthalonitriles. Condensation of the dialkynylphthalonitriles with lithium 1-pentoxide in 1-pentanol gave 2,3,9,10,16,17,23,24-octaalkynylphthalocyanines, while intervention of the intermediate dilithium phthalocyanines with zinc acetate gave the related zinc(II) phthalocyanines. H-1 NMR spectroscopy of these octaalkynylphthalocyanines exhibited large chemical shifts (1-2 ppm) of the internal and aromatic protons at concentrations ranging from 10(-2) to 10(-5) M and at temperatures from 27 to 147 degrees C. The effects of aggregation phenomena are discussed. The importance of reporting concentration and temperature values for NMR spectra of phthalocyanines is stressed.