(1R,9R,12S)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-11,12-dicarboxylic acid dimethyl ester | 600709-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,9R,12S)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-11,12-dicarboxylic acid dimethyl ester
• 英文别名: (1R,9R,12S)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene-11,12-dicarboxylic acid dimethyl ester
• CAS: 600709-03-3
• 化学式: C₁₇H₁₉NO₆
• 分子量: 333.341
• InChiKey: HQWWZMAXUCOMOI-IUPBHXKESA-N

物化性质

• 沸点：
  477.0±45.0 °C(predicted)
• 密度：
  1.295±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,9R,12S)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-11,12-dicarboxylic acid dimethyl ester 在 盐酸 、 三氟化硼乙醚 、 镍 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 144.67h， 生成 (1R,9R,12S)-5-hydroxy-11-azatricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene-12-carboxylic acid hydrochloride salt
  参考文献：
  名称：

  Synthesis of a New Conformation-Constrained l-Tyrosine Analogue as a Potential Scaffold for SH2 Domain Ligands

  摘要：

  The enantioselective synthesis of a new tricyclic tyrosine analogue is reported. This conformation-contrained SH2 domain ligand scaffold 2 was designed on the basis of the natural ligand, whose structure contains the elements of a tyrosine moiety having chi(1) and chi(2) angles constrained to values observed for a phosp(h)otyrosyl (pTyr) residue bound to the p56(lck) SH2 domain. It represents a unique, highly constrained amino acid, which may be of value in signal transduction studies. Three key steps, an asymmetric tandem Michael addition, an intramolecular Friedel-Crafts reaction, and an intramolecular Mannich reaction, were successfully applied in the presented synthetic route.

  DOI：

  10.1021/jo0340152
• 作为产物：
  描述：

  (4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester 在 palladium on activated charcoal 三乙基硅烷 、 lithium hydroxide 、 草酰氯 、 氢气 、 双氧水 、 potassium carbonate 、 potassium hydrogencarbonate 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二硫化碳 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， -5.0~20.0 ℃ 、101.33 kPa 条件下， 反应 22.83h， 生成 (1R,9R,12S)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-11,12-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of a New Conformation-Constrained l-Tyrosine Analogue as a Potential Scaffold for SH2 Domain Ligands

  摘要：

  The enantioselective synthesis of a new tricyclic tyrosine analogue is reported. This conformation-contrained SH2 domain ligand scaffold 2 was designed on the basis of the natural ligand, whose structure contains the elements of a tyrosine moiety having chi(1) and chi(2) angles constrained to values observed for a phosp(h)otyrosyl (pTyr) residue bound to the p56(lck) SH2 domain. It represents a unique, highly constrained amino acid, which may be of value in signal transduction studies. Three key steps, an asymmetric tandem Michael addition, an intramolecular Friedel-Crafts reaction, and an intramolecular Mannich reaction, were successfully applied in the presented synthetic route.

  DOI：

  10.1021/jo0340152