ethyl 4-[6-chloro-9-(methoxymethyl)-2-(trimethylsilyl)-9H-purin-8-yl]benzoate | 1265221-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-[6-chloro-9-(methoxymethyl)-2-(trimethylsilyl)-9H-purin-8-yl]benzoate
• 英文别名: Ethyl 4-[6-chloro-9-(methoxymethyl)-2-trimethylsilylpurin-8-yl]benzoate；ethyl 4-[6-chloro-9-(methoxymethyl)-2-trimethylsilylpurin-8-yl]benzoate
• CAS: 1265221-92-8
• 化学式: C₁₉H₂₃ClN₄O₃Si
• 分子量: 418.955
• InChiKey: CJXRSFBXYUDZRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  79.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-[6-chloro-9-(methoxymethyl)-2-(trimethylsilyl)-9H-purin-8-yl]benzoate 在 zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex 、 palladium on carbon 、 碘 、 异丙基氯化镁 、 ammonium formate 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 24.5h， 生成 ethyl 4-(6-(4-chlorophenyl)-9-(methoxymethyl)-2-(4-methoxyphenyl)-9Hpurin-8-yl)benzoate
  参考文献：
  名称：

  Trifunctionalization of the Purine Scaffold Using Mg and Zn Organometallic Intermediates

  摘要：

  Starting from an appropriate 6-chloro-2-TMS-purine derivative, a regioselective functionalization of the purine scaffold was achieved successively at positions 8, 6, and 2 via zinc and magnesium intermediates which were generated either by a direct zincation with TMPZnCl.LiCl or by an l/Mg exchange with iPrMgCl.

  DOI：

  10.1021/ol103057k
• 作为产物：
  描述：

  6-氯-9-(甲氧基甲基)-9H-嘌呤 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.58h， 生成 ethyl 4-[6-chloro-9-(methoxymethyl)-2-(trimethylsilyl)-9H-purin-8-yl]benzoate
  参考文献：
  名称：

  Trifunctionalization of the Purine Scaffold Using Mg and Zn Organometallic Intermediates

  摘要：

  Starting from an appropriate 6-chloro-2-TMS-purine derivative, a regioselective functionalization of the purine scaffold was achieved successively at positions 8, 6, and 2 via zinc and magnesium intermediates which were generated either by a direct zincation with TMPZnCl.LiCl or by an l/Mg exchange with iPrMgCl.

  DOI：

  10.1021/ol103057k

文献信息

• Regioselective Functionalization of Purine Derivatives at Positions 8 and 6 Using Hindered TMP-Amide Bases of Zn and Mg
  作者：Paul Knochel、François Crestey、Silvia Zimdars

  DOI：10.1055/s-0033-1338524

  日期：——

  A broad range of purine derivatives were efficiently metalated at positions 8 and 6 using TMP-amide bases. This provided polysubstituted purines in good to very good yields after subsequent trapping of the zinc or magnesium intermediates with various electrophiles.
• Trifunctionalization of the Purine Scaffold Using Mg and Zn Organometallic Intermediates
  作者：Silvia Zimdars、Xavier Mollat du Jourdin、François Crestey、Thomas Carell、Paul Knochel

  DOI：10.1021/ol103057k

  日期：2011.2.18

  Starting from an appropriate 6-chloro-2-TMS-purine derivative, a regioselective functionalization of the purine scaffold was achieved successively at positions 8, 6, and 2 via zinc and magnesium intermediates which were generated either by a direct zincation with TMPZnCl.LiCl or by an l/Mg exchange with iPrMgCl.