6-(4-chloro-phenylsulfanyl)-7(9)H-purine | 5457-98-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(4-chloro-phenylsulfanyl)-7(9)H-purine
• 英文别名: 6-(4-Chlor-phenylmercapto)-7(9)H-purin；6-(4-chlorophenyl)sulfanyl-7H-purine
• CAS: 5457-98-7
• 化学式: C₁₁H₇ClN₄S
• 分子量: 262.722
• InChiKey: SFALRJABXVXZCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-chloro-phenylsulfanyl)-7(9)H-purine 在 氨 、 三氯化硼 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 3β-(6-amino-9H-purin-9-yl)cyclobutane-1β-methanol
  参考文献：
  名称：

  Synthesis of 9-[cis-3-(hydroxymethyl)cyclobutyl]-adenine and -guanine

  摘要：

  2,2-Dichloro-3-(benzyloxymethyl)cyclobutanone 15, which was prepared in 50% yield by the cycloaddition of dichloroketene to allyl benzyl ether 14, was converted in four steps and in similar to 40% overall yield into trans-3-(benzyloxymethyl)cyclobutanol 11b. The latter alcohol 11b was coupled under Mitsunobu conditions with 6-(4-chlorophenylsulfanyl)-9H-purine 21b and 6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 21c to give the 9-cyclobutylpurine derivatives 22 and 24, respectively, in 88 and 60% yield. The former product 22 was converted in three steps and in 39% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl]adenine 6, and the latter product was converted in four steps and in 42% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl] guanine 7. X-Ray crystallographic data relating to compounds 22 and 24 are also reported.

  DOI：

  10.1039/p19950002281
• 作为产物：
  描述：

  6-S-(4-氯苯基)-6-硫代-肌苷2’,3’,5’-三乙酸酯 在 三氟化硼乙醚 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到6-(4-chloro-phenylsulfanyl)-7(9)H-purine
  参考文献：
  名称：

  Synthesis of 9-[cis-3-(hydroxymethyl)cyclobutyl]-adenine and -guanine

  摘要：

  2,2-Dichloro-3-(benzyloxymethyl)cyclobutanone 15, which was prepared in 50% yield by the cycloaddition of dichloroketene to allyl benzyl ether 14, was converted in four steps and in similar to 40% overall yield into trans-3-(benzyloxymethyl)cyclobutanol 11b. The latter alcohol 11b was coupled under Mitsunobu conditions with 6-(4-chlorophenylsulfanyl)-9H-purine 21b and 6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 21c to give the 9-cyclobutylpurine derivatives 22 and 24, respectively, in 88 and 60% yield. The former product 22 was converted in three steps and in 39% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl]adenine 6, and the latter product was converted in four steps and in 42% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl] guanine 7. X-Ray crystallographic data relating to compounds 22 and 24 are also reported.

  DOI：

  10.1039/p19950002281

文献信息

• Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes
  作者：Siva Sankar Murthy Bandaru、Shatrughn Bhilare、Jesvita Cardozo、Nicolas Chrysochos、Carola Schulzke、Yogesh S. Sanghvi、Krishna Chaitanya Gunturu、Anant R. Kapdi

  DOI：10.1021/acs.joc.9b00840

  日期：2019.7.19

  Heteroarenes of commercial relevance such as purines and pyrimidines were also found to be useful substrates for the reported transformation. The commercial drug Imuran (azathioprine) was synthesized as an example, and its preparation could be optimized. DFT studies were performed to understand the electronic effects of the tested ligands on the catalytic reaction.

  杂芳基氯化物的硫醚化是必不可少的合成方法，可用于获得生物活性药物和农药。由于它们的（实际或潜在的）工业重要性，出于经济和生态方面的原因，需要开发一种有效的低温协议来获取这些化合物。因此，开发了一种仅在50°C下使用Pd / PTABS系统的高效催化方案。高效率地进行了氯杂芳烃与各种反应性较低的芳基硫醇和烷基硫醇之间的偶联。还发现具有商业意义的杂芳烃，例如嘌呤和嘧啶，是报道的转化的有用底物。以合成的商品药物Imuran（硫唑嘌呤）为例，可以优化其制备方法。
• Cross-Dehydrogenative Coupling of Azoarenes with Dialkyl Disulfides
  作者：Peng Qi、Fang Sun、Ning Chen、Hongguang Du

  DOI：10.1021/acs.joc.0c00953

  日期：2020.7.2

  A catalyst-free cross-dehydrogenative coupling reaction of purines and some azoarenes with dialkyl disulfides has been developed. This procedure provided a novel strategy to construct unsymmetrical disulfides through the α-heterocyclic functionalization of symmetrical dialkyl disulfides. The S–S bond was successfully tolerated in this transformation. The mild conditions and the broad scope of azoarenes

  已开发了嘌呤和一些偶氮芳烃与二烷基二硫化物的无催化剂交叉脱氢偶联反应。该方法提供了一种通过对称二烷基二硫化物的α-杂环官能团构建不对称二硫化物的新策略。在这种转变中成功地容忍了S–S键。温和的条件和偶氮芳烃的广泛范围表明该方法的潜在应用。
• Antimycobacterial Agents. 1. Thio Analogues of Purine
  作者：Ashish K. Pathak、Vibha Pathak、Lainne E. Seitz、William J. Suling、Robert C. Reynolds

  DOI：10.1021/jm030389b

  日期：2004.1.1

  Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 mug/mL respectively against the Mtb H(37)Rv strain. N-9-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.
• HFIP Promoted Low-Temperature S_NAr of Chloroheteroarenes Using Thiols and Amines
  作者：Yuvraj B. Bhujabal、Kamlesh S. Vadagaonkar、Aniket Gholap、Yogesh S. Sanghvi、Rambabu Dandela、Anant R. Kapdi

  DOI：10.1021/acs.joc.9b02371

  日期：2019.12.6

  A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.
• Synthesis of 9-[cis-3-(hydroxymethyl)cyclobutyl]-adenine and -guanine
  作者：Vijay Kaiwar、Colin B. Reese、Emily J. Gray、Stephen Neidle

  DOI：10.1039/p19950002281

  日期：——

  2,2-Dichloro-3-(benzyloxymethyl)cyclobutanone 15, which was prepared in 50% yield by the cycloaddition of dichloroketene to allyl benzyl ether 14, was converted in four steps and in similar to 40% overall yield into trans-3-(benzyloxymethyl)cyclobutanol 11b. The latter alcohol 11b was coupled under Mitsunobu conditions with 6-(4-chlorophenylsulfanyl)-9H-purine 21b and 6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 21c to give the 9-cyclobutylpurine derivatives 22 and 24, respectively, in 88 and 60% yield. The former product 22 was converted in three steps and in 39% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl]adenine 6, and the latter product was converted in four steps and in 42% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl] guanine 7. X-Ray crystallographic data relating to compounds 22 and 24 are also reported.