(R)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid | 1617511-49-5

• 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: (R)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid
• CAS: 1617511-49-5
• 化学式: C₂₈H₂₈N₂O₅
• 分子量: 472.541
• InChiKey: WGVNQCNIGIWFMI-QDPYCGRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  103.78
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (R)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid 在 potassium carbonate 作用下， 以 水 、 丙酮 、 二氯甲烷 为溶剂， 以65%的产率得到(11S)-2,12-diaza-11-benzylpentacyclo[12.5.1.1^1,16.1^14,18.0^4,9]doeicosa-4,6,8-trien-3,10,13-trione
  参考文献：
  名称：

  Memory of chirality in the phthalimide photocyclization of adamantane dipeptides

  摘要：

  Upon sensitized irradiation of N-phthalimido dipeptides containing or D-phenylalanine, enantioselective cyclization to diazamacrocycles takes place (ee >99%). The high optical purity of the products was explained by the memory of chirality effect. The chirality is preserved owing to the axial chirality of the biradical intermediate formed. An insight into the origin behind the enantioselective cyclization of the intermediate was given by density functional calculations. The very high enantiomeric excess in this type of photocyclization establishes it as a new method for the enantioselective synthesis of different large aza-heterocycles. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.118
• 作为产物：
  描述：

  3-(N-phthalimido)adamantane-1-carboxylic acid 在 水 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 (R)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid
  参考文献：
  名称：

  Memory of chirality in the phthalimide photocyclization of adamantane dipeptides

  摘要：

  Upon sensitized irradiation of N-phthalimido dipeptides containing or D-phenylalanine, enantioselective cyclization to diazamacrocycles takes place (ee >99%). The high optical purity of the products was explained by the memory of chirality effect. The chirality is preserved owing to the axial chirality of the biradical intermediate formed. An insight into the origin behind the enantioselective cyclization of the intermediate was given by density functional calculations. The very high enantiomeric excess in this type of photocyclization establishes it as a new method for the enantioselective synthesis of different large aza-heterocycles. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.118