3,6-dibutyl-4,5-(o-xylylenedithio)phthalonitrile | 885694-88-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,6-dibutyl-4,5-(o-xylylenedithio)phthalonitrile
• 英文别名: 4,5-(o-xylylenedithio)-3,6-dibutylphthalonitrile；1,4-Dibutyl-6,11-dihydrobenzo[c][1,6]benzodithiocine-2,3-dicarbonitrile
• CAS: 885694-88-2
• 化学式: C₂₄H₂₆N₂S₂
• 分子量: 406.616
• InChiKey: HWOQKRVXTPZQJC-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  561.2±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-dibutyl-4,5-(o-xylylenedithio)phthalonitrile 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Removal of Xylylene Groups from Tetrakis(o-xylylenedithio)phthalocyanines with Toluene/Aluminum Chloride and Construction of Dithiaphosphole Rings

  摘要：

  Xylylene groups were removed from tetrakis(o-xylylenedithio)-phthalocyanines via C-S bond cleavage by treatment with toluene and aluminum chloride. Octathiolate anions generated were reacted with dichlorophenyl-phosphine to produce phthalocyanines with four dithiaphosphole rings. The structures of the products were determined by NMR and FABMS. Electrochemical and optical properties of them were verified by cyclic voltammetry and UV-vis spectroscopy.

  DOI：

  10.3987/com-14-s(k)58
• 作为产物：
  描述：

  1,2-二(溴甲基)苯 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 3,6-dibutyl-4,5-(o-xylylenedithio)phthalonitrile
  参考文献：
  名称：

  含四个三硫醇环的 1,4,8,11,15,18,22,25-辛烷基酞菁的制备及电化学性质

  摘要：

  1,4,8,11,15,18,22,25-Octalkyl-2,3;9,10;16,17;23,24-tetrakis(o-xylylenedithio)phthalocyanines 4a–d（烷基 = 乙基，丁基通过在正戊醇中用锂处理 3,6-二烷基-4,5-（邻苯二甲硫基）邻苯二甲腈 3a-d，以中等产率制备 ((、辛基和十二烷基)。用锂/四氢呋喃/氨从 4b 和 4c 中还原去除四个邻二甲苯基团，然后用元素硫处理产生的八硫醇阴离子，分别得到新的酞菁 6b 和 6c，每个都含有四个三硫醇环，在相应的酞菁5b和5c部分脱硫和缩环反应后。酞菁的结构由1H NMR光谱和MALDI-TOF质谱确定。在紫外/可见光谱的 λmax ≈ 770 nm 处观察到 4a-d 的 Q 带的吸收，而在一个区域中发现 4b-Ni、5b、5c 和 6c 的吸收，相对于 4a 发生蓝移-d。当在浓硫酸中测量 6c

  DOI：

  10.1002/ejoc.200500654

文献信息

• Preparation and electrochemical and optical properties of α-octaalkylphthalocyanines with four fused TTF units
  作者：Takeshi Kimura、Toshiharu Namauo、Kaori Amano、Nobuhiro Takahashi、Yutaka Takaguchi、Tomonori Hoshi、Nagao Kobayashi

  DOI：10.1142/s1088424611003288

  日期：2011.7

  NMR, FAB MS, and MALDI TOF MS. The 1H NMR measurement was performed in chloroform-d at around 55 °C because of their higher aggregative property. Electrochemical and optical properties of 8a and 8b were examined by cyclic voltammetry and UV-vis and MCD spectroscopy. Molecular orbital calculations succeeded in reproducing the observed absorption spectrum of tetrakis(tetrathiafulvaleno)phthalocyanine.

  3,6-二烷基邻苯二甲腈 (6a) 和 (6b) 在 4,5 位具有稠合 TTF 单元，由二烷基四溴苯通过五步反应（烷基：丁基和辛基）制备。化合物 6a 和 6b 在正己醇中在 120 °C 下用锂处理 3 小时，分别产生 α-八烷基四（四硫富瓦烯）酞菁（8a）和（8b）。产品结构由以下决定1H NMR、FAB MS 和 MALDI TOF MS。这1H NMR 测量是在大约 55°C 的氯仿-d 中进行的，因为它们具有更高的聚集性。8a 和8b 的电化学和光学性质通过循环伏安法和UV-vis 和MCD 光谱法进行了检测。分子轨道计算成功地再现了观察到的四（四硫富瓦烯）酞菁吸收光谱。
• Preparation and Electrochemical Property of Octabutylphthalocyanine Fused with Four TTF Units
  作者：Takeshi Kimura、Dai Watanabe、Toshiharu Namauo

  DOI：10.3987/com-08-s(n)75

  日期：——

  3,6-Dibutylphthalonitrile (3) fused with a TTF unit was prepared and treated with lithium in n-pentanol to produce octabutyltetrakis(tetrathiafulvaleno)phthalocyanine (5). The structure of the product was determined by 1 H NMR and FAB MS. Electrochemical and optical properties of compound (5) were estimated by cyclic voltammetry and UV-vis spectroscopy.

  制备了与 TTF 单元稠合的 3,6-二丁基邻苯二甲腈 (3)，并在正戊醇中用锂处理以生产八丁基四(四硫富瓦烯)酞菁 (5)。产物的结构通过 1 H NMR和FAB MS确定。化合物 (5) 的电化学和光学性质通过循环伏安法和紫外-可见分光光度法进行评估。
• Preparation and reactivity of benzo-1,2-dichalcogenete derivatives and their bis(triphenylphosphine)platinum complexes
  作者：Takeshi Kimura、Tsukasa Nakahodo、Hisashi Fujihara

  DOI：10.1002/hc.21472

  日期：2018.12

  AbstractThe reaction of 4,5‐(o‐xylylenedichalcogeno)‐3,6‐dialkylphthalonitrile (1a‐d) with aluminum chloride in toluene gave ring‐opened products, 3,6‐dialkyl‐4,5‐dicyanobenzene‐1,2‐dithiols (2a,b), for sulfur derivatives and cyclized products, 3,6‐dialkyl‐4‐,5‐dicyanobenzo‐1,2‐diselenetes (2c,d), for selenium derivatives. Asymmetrically substituted 3,6‐diethylbenzo‐1,2‐diselenete (2e) with a bromo and a nitrile group was prepared by the reaction of 4,5‐(o‐xylylenediseleno)‐3,6‐diethyl‐2‐cyano‐1‐bromobenzene (1e) with aluminum chloride in toluene. Compound 2e was unstable compared with 2c and produced an equilibrium mixture of 2e and dimerized dibenzotetraselenocin 3e in the chloroform solution. Compound 2c was reacted with methyl iodide in the presence of sodium hydroxide to produce 1,2‐bis(methylseleno)‐3,6‐diethyl‐4,5‐dicyanobenzene (4) and bis(2‐methylseleno‐3,6‐diethyl‐4,5‐dicyanophenyl)diselenide (5). Compounds 2a and 2c were reacted with tetrakis(triphenylphosphine)platinum in toluene to give the corresponding platinum complexes 6a and 6c with a dichalcogenaplatinumole ring, respectively. The structures of 6a and 6c were determined by NMR, MS, and X‐ray crystallography. To obtain theoretical information, the structures of dichalcogenetes 2a′, 2c, 2e, 2f, 2g and platinum complexes 6a and 6c were optimized by the DFT method using the Gaussian 09 program and their HOMO and LUMO energy levels were calculated by time‐dependent density functional theory.
• Preparation and Optical and Electrochemical Properties of Diphthalocyanine Linked with a TTF Unit
  作者：Takeshi Kimura、Shiduko Nakajo、Shomu Sasaki

  DOI：10.3987/com-16-s(s)55

  日期：——

  4,4',7,7 '-Tetrabuty1-5,5',6,6'-tetracyano-2,2'-bis(benzo-1,3-dithio12-ylidene) (3-Bu) was prepared and mixed with 4,5-bis(2,6-dimethylphenoxy)-phthalonitrile (4), which was treated with lithium alkoxide at 120 C to produce diphthalocyanine linked with a TTF unit. The structure of the product was determined by NMR and MALDI-TOF-MS. The optical and electrochemical properties were examined by UV-vis spectra and cyclic voltammetry.