6-chloro-9-(methoxymethyl)-2-(trimethylsilyl)-9H-purine | 1265221-82-6

• 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: 6-chloro-9-(methoxymethyl)-2-(trimethylsilyl)-9H-purine
• 英文别名: [6-Chloro-9-(methoxymethyl)purin-2-yl]-trimethylsilane
• CAS: 1265221-82-6
• 化学式: C₁₀H₁₅ClN₄OSi
• 分子量: 270.794
• InChiKey: HDESYMYVSOVSNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  373.0±52.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-9-(methoxymethyl)-2-(trimethylsilyl)-9H-purine 在 zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex 、 palladium on carbon 、 碘 、 ammonium formate 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 36.75h， 生成 ethyl 4-(6-(4-chlorophenyl)-2-iodo-9-(methoxymethyl)-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
• 作为产物：
  描述：

  6-氯-9-(甲氧基甲基)-9H-嘌呤 、 三甲基氯硅烷 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.33h， 以60%的产率得到6-chloro-9-(methoxymethyl)-2-(trimethylsilyl)-9H-purine
  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.