Methyl 4-[5-methylsulfanyl-2-(4-methylsulfanylbenzoyl)phenoxy]butanoate | 144888-64-2

• 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: Methyl 4-[5-methylsulfanyl-2-(4-methylsulfanylbenzoyl)phenoxy]butanoate
• CAS: 144888-64-2
• 化学式: C₂₀H₂₂O₄S₂
• 分子量: 390.524
• InChiKey: VOAXVRVIIWDYNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 4-[5-methylsulfanyl-2-(4-methylsulfanylbenzoyl)phenoxy]butanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 4-[5-methylsulfanyl-2-(4-methylsulfanylbenzoyl)phenoxy]butanoic acid
  参考文献：
  名称：

  Safety-catch anchoring linkage for synthesis of peptide amides by Boc/Fmoc strategy

  摘要：

  2-Methoxy-4,4'-bis(methylthio)benzhydrylamine (10) and the corresponding disulfoxide were prepared and tested as a model amide protecting groups for their stability toward acidic conditions. Subsequently, the novel 4-[4,4'-bis(methylsulfinyl)-2-oxy-(9-fluorenylmethyloxycarbonyl) benzhydrylamino]butanoic acid (SCAL) handle (9) has been prepared and applied to solid-phase peptide synthesis of C-terminal peptide amide using both 9-fluorenylmethyloxycarbonyl (Fmoc) and tert-butyloxycarbonyl (Boc) groups for N-alpha-amino protection.

  DOI：

  10.1016/s0040-4039(00)79406-8
• 作为产物：
  描述：

  2,4-二羟基苯甲酸 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三氯化铝 、 氯化亚砜 、 Dowex 50x2 、 sodium hydride 、 四乙基氟化铵水合物 、 三乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 Methyl 4-[5-methylsulfanyl-2-(4-methylsulfanylbenzoyl)phenoxy]butanoate
  参考文献：
  名称：

  Safety-catch anchoring linkage for synthesis of peptide amides by Boc/Fmoc strategy

  摘要：

  2-Methoxy-4,4'-bis(methylthio)benzhydrylamine (10) and the corresponding disulfoxide were prepared and tested as a model amide protecting groups for their stability toward acidic conditions. Subsequently, the novel 4-[4,4'-bis(methylsulfinyl)-2-oxy-(9-fluorenylmethyloxycarbonyl) benzhydrylamino]butanoic acid (SCAL) handle (9) has been prepared and applied to solid-phase peptide synthesis of C-terminal peptide amide using both 9-fluorenylmethyloxycarbonyl (Fmoc) and tert-butyloxycarbonyl (Boc) groups for N-alpha-amino protection.

  DOI：

  10.1016/s0040-4039(00)79406-8

文献信息

• Unusual KF/Al2O3 promoted tandem electrophilic-nucleophilic aromatic substitution leading to the xanthone formation
  作者：Marcel Patek、Michal Lebl、Milos Budesinsky

  DOI：10.1016/s0040-4039(00)60122-3

  日期：1992.7

  Formation of xanthone (III) by the KF/Al2O3 mediated O-alkylation of 2-hydroxybenzophenone (I) is described and mechanistic rationalization is proposed for this unexpected side-reaction.
• Safety-catch anchoring linkage for synthesis of peptide amides by Boc/Fmoc strategy
  作者：Marcel Pátek、Michal Lebl

  DOI：10.1016/s0040-4039(00)79406-8

  日期：1991.7

  2-Methoxy-4,4'-bis(methylthio)benzhydrylamine (10) and the corresponding disulfoxide were prepared and tested as a model amide protecting groups for their stability toward acidic conditions. Subsequently, the novel 4-[4,4'-bis(methylsulfinyl)-2-oxy-(9-fluorenylmethyloxycarbonyl) benzhydrylamino]butanoic acid (SCAL) handle (9) has been prepared and applied to solid-phase peptide synthesis of C-terminal peptide amide using both 9-fluorenylmethyloxycarbonyl (Fmoc) and tert-butyloxycarbonyl (Boc) groups for N-alpha-amino protection.