9-[(1R,2S,3S)-4-bromo-2,3-isopropylidenedioxy-4-cyclopenten-1-yl]adenine | 1062238-68-9

• 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: 9-[(1R,2S,3S)-4-bromo-2,3-isopropylidenedioxy-4-cyclopenten-1-yl]adenine
• CAS: 1062238-68-9
• 化学式: C₁₃H₁₄BrN₅O₂
• 分子量: 352.19
• InChiKey: WSAHAZDSPOZMDV-QNSHHTMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.08
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9-[(1R,2S,3S)-4-bromo-2,3-isopropylidenedioxy-4-cyclopenten-1-yl]adenine 在 甲酸 作用下， 生成 9-[(1R,2S,3S)-4-bromo-2,3-dihydroxy-4-cyclopenten-1-yl]adenine
  参考文献：
  名称：

  新型4'修饰的neplanocin A类似物的合成及其对S-腺苷-Ll-同型半胱氨酸水解酶的抑制作用

  摘要：

  开发了一种新的合成4'-修饰的neplanocin A类似物的新方法，作为对抗S-腺苷-L-高半胱氨酸水解酶的潜在抑制剂。乙烯基锡烷13是本方法的关键中间体，它是通过自由基介导的硫原子挤压性苯乙烯基化反应制备的。

  DOI：

  10.1080/15257770701493617
• 作为产物：
  描述：

  9-[(1R,2S,3S)-2,3-isopropylidenedioxy-4-tributylstannyl-4-cyclopenten-1-yl]adenine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以67%的产率得到9-[(1R,2S,3S)-4-bromo-2,3-isopropylidenedioxy-4-cyclopenten-1-yl]adenine
  参考文献：
  名称：

  Radical-mediated stannylation of vinyl sulfones: access to novel 4′-modified neplanocin A analogues

  摘要：

  Synthesis of 4'-substituted (halogeno, phenyl, ethynyl, and cyano) neplanocin A analogues was carried out. A cyclopentenol derivative having a vinylstannane structure was designed as key-intermediate in this study, which was prepared based on radical-mediated sulfur-extrusive stannylation. The resulting stannylated cyclopentenol 15 was successfully condensed with 6-chloropurine through the Mitsunobu reaction, leading to the carbocyclic nucleoside 20. Compound 20 was converted to its adenine counterpart 21 by treatment with NH(3)/MeOH, during which the 4'-stannyl group remained intact. The title compounds were prepared by using 21 or the 4'-iodo derivative (22) mostly through the Stille reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.039