4-(6-Benzylsulfanyl-9-propan-2-ylpurin-2-yl)but-3-yn-1-ol | 403620-93-9

• 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: 4-(6-Benzylsulfanyl-9-propan-2-ylpurin-2-yl)but-3-yn-1-ol
• CAS: 403620-93-9
• 化学式: C₁₉H₂₀N₄OS
• 分子量: 352.46
• InChiKey: QJFLTRJHGAAYPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  89.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(6-Benzylsulfanyl-9-propan-2-ylpurin-2-yl)but-3-yn-1-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以63%的产率得到4-(6-Benzylsulfonyl-9-propan-2-ylpurin-2-yl)but-3-yn-1-ol
  参考文献：
  名称：

  Cyclin-dependent kinase (CDK) inhibitors: development of a general strategy for the construction of 2,6,9-trisubstituted purine libraries. Part 1

  摘要：

  To validate a proposed solid support synthesis strategy for the construction of 2,6,9-trisubstituted purine based CDK inhibitors, the N-9 THP protected 6-benzylthio-2-iodopurine 11 was reacted with piperidine-2-methanol to give 12. Alternatively, intermediate It was converted to the C-2 acetylenyl substituted purine 16 in five steps, involving N-9 alkylation (Mitsunobu reaction), a Pd(0)-CuI-catalyzed acetylene coupling, selective activation of the 6-sulfur substituent and its displacement by ArCH2NH2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01751-8
• 作为产物：
  描述：

  6-chloro-2-iodo-9-(tetrahydropyran-2-yl)purine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 水 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 4-(6-Benzylsulfanyl-9-propan-2-ylpurin-2-yl)but-3-yn-1-ol
  参考文献：
  名称：

  Cyclin-dependent kinase (CDK) inhibitors: development of a general strategy for the construction of 2,6,9-trisubstituted purine libraries. Part 1

  摘要：

  To validate a proposed solid support synthesis strategy for the construction of 2,6,9-trisubstituted purine based CDK inhibitors, the N-9 THP protected 6-benzylthio-2-iodopurine 11 was reacted with piperidine-2-methanol to give 12. Alternatively, intermediate It was converted to the C-2 acetylenyl substituted purine 16 in five steps, involving N-9 alkylation (Mitsunobu reaction), a Pd(0)-CuI-catalyzed acetylene coupling, selective activation of the 6-sulfur substituent and its displacement by ArCH2NH2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01751-8