[(1R,4R)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl] acetate | 332187-83-4

• 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: [(1R,4R)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl] acetate
• CAS: 332187-83-4
• 化学式: C₁₂H₁₃N₅O₂
• 分子量: 259.268
• InChiKey: QQTBSDJCIIKERB-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1R,4R)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl] acetate 在 甲醇 、 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 叠氮化锂 、 氨 、 水 、 三乙胺 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidenedioxy-4'-cyclopenten-1'-yl]-9-H-adenine
  参考文献：
  名称：

  Facile synthesis of 9-[(1′R,2′S)-2′-hydroxy-3′-oxocyclopentan-1′-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-l-homocysteine hydrolase

  摘要：

  Treatment of 4'-O-methanesulfonyl-2',3'-O-isopropylideneoraisteromycin with KOBut gave the corresponding 3',4'-dehydro derivative, and subsequent deprotection resulted in the formation of 9-[(1'R,2'S)-2'-hydroxy-3'-oxocyclopentan-1'-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-L homocysteine hydrolase (EC 3.3.1.1). In sharp contrast to KOBut, when lithium azide was adopted as a base, 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidened ioxy-4'-cyclopenten-1'-yl]-H-adenine was selectively obtained, and subsequent deprotection afforded DHCeA, which is a well-known potential antiviral agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01978-x
• 作为产物：
  描述：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 、 腺嘌呤 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到[(1R,4R)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl] acetate
  参考文献：
  名称：

  Facile synthesis of 9-[(1′R,2′S)-2′-hydroxy-3′-oxocyclopentan-1′-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-l-homocysteine hydrolase

  摘要：

  Treatment of 4'-O-methanesulfonyl-2',3'-O-isopropylideneoraisteromycin with KOBut gave the corresponding 3',4'-dehydro derivative, and subsequent deprotection resulted in the formation of 9-[(1'R,2'S)-2'-hydroxy-3'-oxocyclopentan-1'-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-L homocysteine hydrolase (EC 3.3.1.1). In sharp contrast to KOBut, when lithium azide was adopted as a base, 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidened ioxy-4'-cyclopenten-1'-yl]-H-adenine was selectively obtained, and subsequent deprotection afforded DHCeA, which is a well-known potential antiviral agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01978-x