(1R,9R,12R)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene-12-carboxylic acid methyl ester | 600709-06-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,9R,12R)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene-12-carboxylic acid methyl ester
• 英文别名: methyl (1R,9R,12R)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-12-carboxylate
• CAS: 600709-06-6
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: OVSACVNYRYPMCL-XTWCZFFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯甲酸甲酯 、 (1R,9R,12R)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene-12-carboxylic acid methyl ester 在 potassium hydrogencarbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (1R,9R,12R)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.0^2,7]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
• 作为产物：
  描述：

  在 palladium on activated charcoal 三乙基硅烷 、 草酰氯 、 氢气 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二硫化碳 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 22.33h， 生成 (1R,9R,12R)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene-12-carboxylic acid methyl 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

文献信息

• Synthesis of a New Conformation-Constrained <scp>l</scp>-Tyrosine Analogue as a Potential Scaffold for SH2 Domain Ligands
  作者：Fa Liu、Hui-Yan Zha、Zhu-Jun Yao

  DOI：10.1021/jo0340152

  日期：2003.8.1

  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.