2,5,6-trichloro-4-(methylthio)isophthalonitrile | 39145-58-9

• 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: 2,5,6-trichloro-4-(methylthio)isophthalonitrile
• 英文别名: 2,5,6-trichloro-4-thiomethyl-1,3-dicyanobenzene；4-methylthio-2,5,6-trichloro-1,3-dicyanobenzene；2,5,6-trichloro-4-methylthioisophthalonitrile；2,4,5-trichloro-6-(methylthio)-benzene-1,3-dicarbonitrile；2.4.5-Trichlor-6-(methylthio)isophthalonitril；Methylthiotrichloroisophthalonitrile；2,4,5-trichloro-6-methylsulfanylbenzene-1,3-dicarbonitrile
• CAS: 39145-58-9
• 化学式: C₉H₃Cl₃N₂S
• 分子量: 277.561
• InChiKey: OPFZHDLMZNKUQG-UHFFFAOYSA-N

物化性质

• 沸点：
  361.4±42.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  百菌清 、 sodium thiomethoxide 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以10%的产率得到2,5-dichloro-4,6-dithiomethyl-1,3-dicyanobenzene
  参考文献：
  名称：

  Preparation and properties of glutathion conjugates of 2,4,5,6-tetrachloro-1,3-dicyanobenzene

  摘要：

  Preparation and spectroscopic properties of 2,5,6-trichloro-4-(S-gamma-L-glutamyl-L-cysteinyl-glycine)-1.3-dicyanobenzene (2), 2,5-dichloro-4,6-di-(S-gamma-L-glutamyl-L-cysteinyl-glycine)- 1,3-dicyanobenzene (3), and 5-chloro-2,4,6-tri(S-gamma-L-glutamyl-L-cysteinyl-glycine)-1,3-dicyanobenzene (4), gluthation conjugates of the general fungicide chlorothalonil (2,4,5,6-tetrachloro-1,3-dicyanobenzene, 1) are reported. Optimal conditions for preparation and chromatographic separation of the single conjugates are described. NMR-spectroscapic data allowed unambiguous determination of regioselectivity of conjugation reaction of chlorothalonil with glutathione. UV Spectra of 24 revealed significant long-wavelength band shift and enhancement of intensity with increasing number of thioalkyl groups attached to the aromatic ring. The UV band assignement is based on the UV-VIS spectra of the model compounds 5-7. The far-UV CD spectra are dominated by the chiral contribution of the amide chromophores. In a trifluoroethanol/water (70:30) mixture the peptide backbone of conjugate 2 likely adopts an ordered (folded) conformation, whereas peptides 3 and 4 show no significant tendency for forming ordered structures.

  DOI：

  10.1016/0040-4020(94)01090-m

文献信息

• US4069342A
  申请人：——

  公开号：US4069342A

  公开（公告）日：1978-01-17
• Preparation and properties of glutathion conjugates of 2,4,5,6-tetrachloro-1,3-dicyanobenzene
  作者：Zdenko Hameršak、Miklos Hollósi、Darko Kontrec、Branko Ladešié、Zsuzsa Majer、Vitomir Šunjić

  DOI：10.1016/0040-4020(94)01090-m

  日期：1995.2

  Preparation and spectroscopic properties of 2,5,6-trichloro-4-(S-gamma-L-glutamyl-L-cysteinyl-glycine)-1.3-dicyanobenzene (2), 2,5-dichloro-4,6-di-(S-gamma-L-glutamyl-L-cysteinyl-glycine)- 1,3-dicyanobenzene (3), and 5-chloro-2,4,6-tri(S-gamma-L-glutamyl-L-cysteinyl-glycine)-1,3-dicyanobenzene (4), gluthation conjugates of the general fungicide chlorothalonil (2,4,5,6-tetrachloro-1,3-dicyanobenzene, 1) are reported. Optimal conditions for preparation and chromatographic separation of the single conjugates are described. NMR-spectroscapic data allowed unambiguous determination of regioselectivity of conjugation reaction of chlorothalonil with glutathione. UV Spectra of 24 revealed significant long-wavelength band shift and enhancement of intensity with increasing number of thioalkyl groups attached to the aromatic ring. The UV band assignement is based on the UV-VIS spectra of the model compounds 5-7. The far-UV CD spectra are dominated by the chiral contribution of the amide chromophores. In a trifluoroethanol/water (70:30) mixture the peptide backbone of conjugate 2 likely adopts an ordered (folded) conformation, whereas peptides 3 and 4 show no significant tendency for forming ordered structures.