1-(甲基二硫烷基)-2,4-二硝基苯 | 61337-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(甲基二硫烷基)-2,4-二硝基苯
• 英文名称: 2,4-dinitrophenyl methyl disulfide
• 英文别名: (2,4-dinitro-phenyl)-methyl disulfide；(2,4-Dinitro-phenyl)-methyl-disulfid；Methyl-2.4-dinitrophenyl-disulfid；1-(Methyldisulfanyl)-2,4-dinitrobenzene
• CAS: 61337-18-6
• 化学式: C₇H₆N₂O₄S₂
• 分子量: 246.268
• InChiKey: DGZRWIPJYVKMHE-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  368.3±42.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(甲基二硫烷基)-2,4-二硝基苯 、 1-benzyl 4-methyl (2S)-2-[[(tert-butoxy)carbonyl]amino]butanedioate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以16%的产率得到(2R,3R)-N-tert-butoxycarbonyl-3-methylsulfanylaspartic acid 1-benzyl ester 4-methyl ester
  参考文献：
  名称：

  Synthesis of β-(S-methyl)thioaspartic acid and derivatives

  摘要：

  beta-(S-Methyl)thioaspartic acid occurs as a posttranslational modi. cation at position 88 in Escherichia coli ribosomal protein S12, a position that is a mutational hotspot resulting in both antibiotic-resistant and antibiotic-sensitive phenotypes. Critical to research designed to determine the biological function of beta-(S-methyl) thioaspartic acid will be the availability of synthetic beta-(S-methyl) thioaspartic acid as well as derivatives designed for peptide incorporation. We report here the synthesis of beta-(S-methyl) thioaspartic acid and derivatives. The installation of the beta-methylthio moiety into the aspartic acid structure was accomplished by electrophilic sulfenylation of N-protected-L-aspartic acid derivatives with 2,4-dinitrophenyl methyl disulfide. Following this key transformation, we were able to prepare protected beta-(S-methyl) thioaspartic acid derivative suitable for peptide coupling. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.04.069
• 作为产物：
  描述：

  2,4-二硝基苯硫氯 、 二甲基亚砜 以 乙腈 为溶剂， 反应 0.17h， 以77%的产率得到1-(甲基二硫烷基)-2,4-二硝基苯
  参考文献：
  名称：

  Synthesis of β-(S-methyl)thioaspartic acid and derivatives

  摘要：

  beta-(S-Methyl)thioaspartic acid occurs as a posttranslational modi. cation at position 88 in Escherichia coli ribosomal protein S12, a position that is a mutational hotspot resulting in both antibiotic-resistant and antibiotic-sensitive phenotypes. Critical to research designed to determine the biological function of beta-(S-methyl) thioaspartic acid will be the availability of synthetic beta-(S-methyl) thioaspartic acid as well as derivatives designed for peptide incorporation. We report here the synthesis of beta-(S-methyl) thioaspartic acid and derivatives. The installation of the beta-methylthio moiety into the aspartic acid structure was accomplished by electrophilic sulfenylation of N-protected-L-aspartic acid derivatives with 2,4-dinitrophenyl methyl disulfide. Following this key transformation, we were able to prepare protected beta-(S-methyl) thioaspartic acid derivative suitable for peptide coupling. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.04.069

文献信息

• Boehme; Stachel, Zeitschrift fur Analytische Chemie, 1957, vol. 154, p. 27
  作者：Boehme、Stachel

  DOI：——

  日期：——
• US5858179A
  申请人：——

  公开号：US5858179A

  公开（公告）日：1999-01-12
• Synthesis of β-(S-methyl)thioaspartic acid and derivatives
  作者：Jorge Heredia-Moya、Kenneth L. Kirk

  DOI：10.1016/j.bmc.2008.04.069

  日期：2008.6

  beta-(S-Methyl)thioaspartic acid occurs as a posttranslational modi. cation at position 88 in Escherichia coli ribosomal protein S12, a position that is a mutational hotspot resulting in both antibiotic-resistant and antibiotic-sensitive phenotypes. Critical to research designed to determine the biological function of beta-(S-methyl) thioaspartic acid will be the availability of synthetic beta-(S-methyl) thioaspartic acid as well as derivatives designed for peptide incorporation. We report here the synthesis of beta-(S-methyl) thioaspartic acid and derivatives. The installation of the beta-methylthio moiety into the aspartic acid structure was accomplished by electrophilic sulfenylation of N-protected-L-aspartic acid derivatives with 2,4-dinitrophenyl methyl disulfide. Following this key transformation, we were able to prepare protected beta-(S-methyl) thioaspartic acid derivative suitable for peptide coupling. Published by Elsevier Ltd.