9-benzyl-6-chloro-7,8-dihydropurine | 1258274-70-2

• 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-benzyl-6-chloro-7,8-dihydropurine
• 英文别名: 6-chloro-9-benzyl-7,8-dihydropurine；9-Benzyl-6-chloro-7,8-dihydropurine
• CAS: 1258274-70-2
• 化学式: C₁₂H₁₁ClN₄
• 分子量: 246.699
• InChiKey: YXTJSQHIBKUDJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  450.9±45.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-benzyl-6-chloro-7,8-dihydropurine 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 11.0h， 生成 9-benzyl-6-(N,N-diethylamino)-9H-purine
  参考文献：
  名称：

  Selective Synthesis of 7-Substituted Purines via 7,8-Dihydropurines

  摘要：

  A simple and efficient protocol for the preparation of 7-substituted purines is described. 6- and 2,6-Dihalopurines were N-9-tritylated and then transformed to 7,8-dihydropurines by DIBAL-H. Subsequent N-7-alkylation followed by N-9-trityl deprotection with trifluoroacetic acid was accompanied by spontaneous reoxidation, which led to the 7-substituted purines at 55-88% overall isolated yields.

  DOI：

  10.1021/ol1025525
• 作为产物：
  描述：

  6-氯-9-(苯基甲基)-9H-嘌呤 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 9-benzyl-6-chloro-7,8-dihydropurine
  参考文献：
  名称：

  Regioselective and Facile Synthesis of 7,9-Dialkyl-8-oxopurines from 7,9-Dialkyl-7,8-dihydropurines: Total Synthesis of Heteromines I and J

  摘要：

  A novel protocol for the synthesis of 6-halo-8-oxo-7,8-dihydro- 9H-purines based on the oxidation of 7,9-dialkyl-7,8-dihydro-9H-purines has been developed. The presented methodology was used as a key step in the synthesis of heteromines I and J.

  DOI：

  10.1055/s-0033-1340499

文献信息

• Highly Efficient and Broad-Scope Protocol for the Preparation of 7-Substituted 6-Halopurines via N9-Boc-Protected 7,8-Dihydropurines
  作者：Dalimil Dvořák、Vladislav Kotek、Tomáš Tobrman

  DOI：10.1055/s-0031-1290068

  日期：2012.2

  9-Boc-6-chloropurine, which can be obtained in high yield, is nearly quantitatively reduced with the THF˙BH3 complex. The obtained 9-Boc-7,8-dihydropurine derivative is more stable compared to the corresponding 9-tritylpurine and can be smoothly N7-alkylated, acylated, or it can serve as an N-nucleophile in conjugate additions. Deprotection with trifluoroacetic acid followed by MnO2 oxidation affords the N7-substituted purines in high yields. The whole sequence of alkylation, deprotection, and oxidation can be done with crude intermediates using chromatography only for the purification of the final N7-substituted purine.

  高产率可获得的9-Boc-6-氯嘌呤几乎可以定量地被THF-BH3复合物还原。所得到的9-Boc-7,8-二氢嘌呤衍生物相比于相应的9-三苯甲基嘌呤更加稳定，并且可以顺利地进行N7-烷基化、酰基化或作为N-亲核试剂参与共轭加成。使用三氟乙酸脱保护后，再经MnO2氧化，可获得高产率的N7-取代嘌呤。整个烷基化、脱保护和氧化的序列可以在使用色谱法仅对最终的N7-取代嘌呤进行纯化的条件下，利用粗中间体完成。