(S)-4-[(2'-amino-6'-chloropurin-9-yl)methyl]azetin-2-one | 517877-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (S)-4-[(2'-amino-6'-chloropurin-9-yl)methyl]azetin-2-one
• CAS: 517877-43-9
• 化学式: C₉H₉ClN₆O
• 分子量: 252.663
• InChiKey: RSWRHBLYZZLWKP-BYPYZUCNSA-N

物化性质

• 密度：
  2.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.72
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-4-[(2'-amino-6'-chloropurin-9-yl)methyl]azetin-2-one 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 129.0h， 生成 (S)-N-[(tert-butoxy)carbonyl]-γ-(guanin-9-yl)-β-homoalanine
  参考文献：
  名称：

  Nucleo--Amino Acids: Synthesis and Oligomerization to -Homoalanyl-PNA

  摘要：

  The synthesis of thyminyl-, uracilyl-, cytosinyl-, and guaninyl-beta(3)-amino acids and the oligomerization of the cytosinyl- and guaninyl-beta(3)-amino acids to beta-homoalanyl-PNA are presented. The pyrimidinyl nucleobases were connected to the gamma-position of beta-homoalanine by Mitsunobu reaction with a beta-homoserine derivative or by nucleophilic substitution of methanesulfonates. For the preparation of the guaninyl-beta(3)-amino acid, a beta-lactam route was established that might be of interest also for the synthesis of other beta(3)-amino acid derivatives. The cytosinyl and guaninyl building blocks were oligomerized to hexamers. They form quite stable self-pairing complexes in H2O as indicated by temperature dependent UV and CD spectroscopy.

  DOI：

  10.1002/1522-2675(200211)85:11<3855::aid-hlca3855>3.0.co;2-a
• 作为产物：
  描述：

  4(S)-4-methanesulfonyloxymethyl azetidin-2-one 、 2-氨基-6-氯嘌呤 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以39%的产率得到(S)-4-[(2'-amino-6'-chloropurin-9-yl)methyl]azetin-2-one
  参考文献：
  名称：

  Nucleo--Amino Acids: Synthesis and Oligomerization to -Homoalanyl-PNA

  摘要：

  The synthesis of thyminyl-, uracilyl-, cytosinyl-, and guaninyl-beta(3)-amino acids and the oligomerization of the cytosinyl- and guaninyl-beta(3)-amino acids to beta-homoalanyl-PNA are presented. The pyrimidinyl nucleobases were connected to the gamma-position of beta-homoalanine by Mitsunobu reaction with a beta-homoserine derivative or by nucleophilic substitution of methanesulfonates. For the preparation of the guaninyl-beta(3)-amino acid, a beta-lactam route was established that might be of interest also for the synthesis of other beta(3)-amino acid derivatives. The cytosinyl and guaninyl building blocks were oligomerized to hexamers. They form quite stable self-pairing complexes in H2O as indicated by temperature dependent UV and CD spectroscopy.

  DOI：

  10.1002/1522-2675(200211)85:11<3855::aid-hlca3855>3.0.co;2-a