2-amino-6-(phenylsulfanyl)purine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-amino-6-(phenylsulfanyl)purine
• 英文别名: 6-phenylsulfanyl-7H-purin-2-amine
• 化学式: C₁₁H₉N₅S
• 分子量: 243.292
• InChiKey: ZVUURIFSHZHQPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  鸟嘌呤 、 苯硫酚 在 三氟乙酸酐 作用下， 生成 2-amino-6-(phenylsulfanyl)purine
  参考文献：
  名称：

  Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir)

  摘要：

  Guanine 11 was converted, in a one pot reaction, into 2-amino-6-[(4-chlorophenyl)sulfanyl]purine 9a in 88% isolated yield. 4-Acetoxy-3-(acetoxymethyl)butanol 23 was prepared from 2-chloroethanol in five steps and in 46% overall yield. The mesylate ester of compound 23 reacted with 9a in the presence of potassium carbonate with a high degree of regioselectivity (89%) to give the N-9 alkylated product 26 which was isolated in 80% yield. Acidic hydrolysis of the latter compound 26 gave penciclovir 4 in virtually quantitative yield. Penciclovir 4 and famciclovir 5 were prepared from 2-amino-6-[(4-chlorophenyl)sulfanyl]puri 9a in four and five steps, respectively, by procedures involving initial alkylation with 1,2-dibromoethane. The overall yields obtained were 65 and ca. 60%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00169-6

文献信息

• An efficient synthesis of substituted cytosines and purines under focused microwave irradiation
  作者：Ling-Kuen Huang、Yen-Chih Cherng、Yann-Ru Cheng、Jing-Pei Jang、Yi-Ling Chao、Yie-Jia Cherng

  DOI：10.1016/j.tet.2007.02.124

  日期：2007.6

  A rapid nucleophilic displacement reaction of 6-chloropurine, 2-amino-6-chloropurine and 5-bromocytosine with various nucleophiles under focused microwave irradiation is described. Using this method, the desired products were obtained with the yields up to 99% in a short reaction time.

  描述了在聚焦微波辐射下6-氯嘌呤，2-氨基-6-氯嘌呤和5-溴胞嘧啶与各种亲核试剂的快速亲核取代反应。使用这种方法，可以在较短的反应时间内获得高达99％的收率的所需产物。
• Copper Catalyzed Three-Component Ullmann C–S Coupling in PEG for the Synthesis of 6-Aryl/alkylthio-purines
  作者：Panpan Zhang、Yunfang Liu、Xulian Li、Geling Siri、Jieyuan Wang、Zhen Li、Yajun Jian、Ziwei Gao

  DOI：10.1021/acs.joc.3c02116

  日期：2024.2.16