2,6-dichloro-9-((methoxycarbonyl)methyl)-9H-purine | 862374-04-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,6-dichloro-9-((methoxycarbonyl)methyl)-9H-purine
• 英文别名: Methyl 2-(2,6-dichloro-9H-purin-9-yl)acetate；methyl 2-(2,6-dichloropurin-9-yl)acetate
• CAS: 862374-04-7
• 化学式: C₈H₆Cl₂N₄O₂
• 分子量: 261.067
• InChiKey: CYFDDQDGJBCBOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-dichloro-9-((methoxycarbonyl)methyl)-9H-purine 在 sodium azide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 96.0h， 以20%的产率得到(2,6-Diazido-purin-9-yl)-acetic acid methyl ester
  参考文献：
  名称：

  2,6-Diazido-9-(carboxymethyl)purine Methyl Ester

  摘要：

  The title compound (methyl 2,6-diazidopurine-9-acetate. C8H6N10O2) is a potential intermediate for the synthesis of peptidic nucleic acids containing diaminopurine. Its two azido groups are approximately parallel and at their attachment points, the internal ring angles are 1.4(3)degrees smaller than in the dichloro homologue.

  DOI：

  10.1107/s0108270196015764
• 作为产物：
  描述：

  氯乙酸甲酯 、 2,6-二氯嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.13h， 以74%的产率得到2,6-dichloro-9-((methoxycarbonyl)methyl)-9H-purine
  参考文献：
  名称：

  微波促进的N-（烷氧基羰基甲基）核碱基的便捷高效制备-肽核酸的基础。

  摘要：

  开发了一种简单，快速和区域选择性的方法，用于合成N-（甲氧基-羰基甲基）-和N-（正丙氧基羰基甲基）核碱基。通过使用DMF作为溶剂并在K2CO3作为碱的存在下，在微波辐射下，在8分钟内以中等收率获得了所有所需产物。

  DOI：

  10.3390/12030543

文献信息

• Tetrabutylammonium fluoride-assisted rapid N9-alkylation on purine ring: Application to combinatorial reactions in microtiter plates for the discovery of potent sulfotransferase inhibitors in situ
  作者：Ashraf Brik、Chung-Yi Wu、Michael D. Best、Chi-Huey Wong

  DOI：10.1016/j.bmc.2005.02.066

  日期：2005.8

  been invested in the synthesis of purine libraries due to their importance in targeting various enzymes involved in different diseases and cellular processes. The synthesis of N9-alkylated purine scaffolds relied mostly on Mitsunobu conditions with a variety of alcohols or strong basic conditions with different organic halides. A more reliable and efficient way for the synthesis of N(9)-alkylated purine

  由于嘌呤文库对于靶向涉及不同疾病和细胞过程的各种酶具有重要意义，因此已在嘌呤文库的合成方面投入了大量精力。N9-烷基化嘌呤支架的合成主要依赖于Mitsunobu条件下的各种醇类或强碱性条件下的不同有机卤化物。报道了一种更可靠和有效的合成N（9）-烷基化嘌呤支架的方法。该方法使用氟化四丁基铵（TBAF）来辅助这种化学反应。在许多情况下，反应在10分钟内完成，并以高收率和选择性提供了所需的产物。此外，这些温和的反应条件使其可用于微量滴定板的组合反应，然后进行原位筛选以发现有效的磺基转移酶抑制剂。
• Synthesis of Novel C6-Phosphonated Purine Nucleosides under Microwave Irradiation by SNAr−Arbuzov Reaction
  作者：Gui-Rong Qu、Ran Xia、Xi-Ning Yang、Jian-Guo Li、Dong-Chao Wang、Hai-Ming Guo

  DOI：10.1021/jo702680p

  日期：2008.3.1

  Novel C6-phosphonated purine nucleosides were obtained in good to excellent isolated yields by the simple and catalyst-free SNAr−Arbuzov reaction of trialkyl phosphite with 6-choloropurine nucleosides, including a series of nonsugar carbon nucleosides. Shorter reaction times were needed, and substantially higher yields were obtained under microwave irradiation conditions compared with conventional

  通过亚磷酸三烷基酯与6-胆嘌呤核苷的简单且无催化剂的SNAr-Arbuzov反应，包括一系列非糖碳核苷，可以很好地分离出高产的新型C6-膦化嘌呤核苷。与常规加热条件相比，需要更短的反应时间，并且在微波辐射条件下获得了实质上更高的产率。
• COMPOUNDS, COMPOSITIONS, AND METHODS FOR THE TREATMENT OF DISEASE
  申请人：F-STAR THERAPEUTICS, INC.

  公开号：US20220168309A1

  公开（公告）日：2022-06-02

  Disclosed are compounds and compositions for inhibiting the expression of a pattern recognition receptor (e.g., STING), and methods of use thereof.
• Microwave-promoted Facile and Efficient Preparation of N-(alkoxycarbonylmethyl) Nucleobases − Building Blocks for Peptide Nucleic Acids
  作者：Guirong Qu、Zhiguang Zhang、Haiming Guo、Mingwei Geng、Ran Xia

  DOI：10.3390/12030543

  日期：——

  A simple, rapid, and regioselective approach for the synthesis of N-(methoxy-carbonylmethyl)- and N-(n-propoxycarbonylmethyl) nucleobases was developed. By using DMF as the solvent and in the presence of K2CO3 as the base, all the desired products were obtained in moderate yields within 8 min under microwave irradiation.

  开发了一种简单，快速和区域选择性的方法，用于合成N-（甲氧基-羰基甲基）-和N-（正丙氧基羰基甲基）核碱基。通过使用DMF作为溶剂并在K2CO3作为碱的存在下，在微波辐射下，在8分钟内以中等收率获得了所有所需产物。
• 2,6-Diazido-9-(carboxymethyl)purine Methyl Ester
  作者：G. Sood、C. H. Schwalbe、W. Fraser

  DOI：10.1107/s0108270196015764

  日期：1997.5.15

  The title compound (methyl 2,6-diazidopurine-9-acetate. C8H6N10O2) is a potential intermediate for the synthesis of peptidic nucleic acids containing diaminopurine. Its two azido groups are approximately parallel and at their attachment points, the internal ring angles are 1.4(3)degrees smaller than in the dichloro homologue.