dimethyl 2-[2-(guanin-9-yl)ethyl]malonate | 234110-23-7

• 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: dimethyl 2-[2-(guanin-9-yl)ethyl]malonate
• 英文别名: dimethyl 2-[2-(2-amino-6-oxo-1H-purin-9-yl)ethyl]propanedioate
• CAS: 234110-23-7
• 化学式: C₁₂H₁₅N₅O₅
• 分子量: 309.282
• InChiKey: JYIXEACFDQQJKO-UHFFFAOYSA-N

物化性质

• 熔点：
  226 °C (decomp)(Solv: methanol (67-56-1))
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 2-[2-(guanin-9-yl)ethyl]malonate 在 四乙基氯化铵 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以70%的产率得到[2-(2-氨基-6-氯-9H-嘌呤-9-基)乙基]丙二酸二甲酯
  参考文献：
  名称：

  Improved Industrial Syntheses of Penciclovir and Famciclovir Using N2-Acetyl-7-Benzylguanine and a Cyclic Side Chain Precursor

  摘要：

  We have established practical synthetic methods for penciclovir (PCV, 1) and famciclovir (FCV, 2) from N2-acetyl-7-benzylguanine (NAc7BnG, 3) and 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (4)-the latter being a more easily prepared cyclic precursor of the diacetate side chain (5) used in the conventional process. The coupling of 4 with 3 proceeded regioselectively at the N9 position of guanine in good yield. The coupling product was then successfully transformed into the known antiviral agents in a short number of steps.

  DOI：

  10.1080/15257770600686279
• 作为产物：
  描述：

  N²-acetyl-7-benzylguanine 在 palladium on activated charcoal 盐酸 、 氯化亚砜 、 氢气 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 40.0~70.0 ℃ 、101.33 kPa 条件下， 反应 34.0h， 生成 dimethyl 2-[2-(guanin-9-yl)ethyl]malonate
  参考文献：
  名称：

  Improved Industrial Syntheses of Penciclovir and Famciclovir Using N2-Acetyl-7-Benzylguanine and a Cyclic Side Chain Precursor

  摘要：

  We have established practical synthetic methods for penciclovir (PCV, 1) and famciclovir (FCV, 2) from N2-acetyl-7-benzylguanine (NAc7BnG, 3) and 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (4)-the latter being a more easily prepared cyclic precursor of the diacetate side chain (5) used in the conventional process. The coupling of 4 with 3 proceeded regioselectively at the N9 position of guanine in good yield. The coupling product was then successfully transformed into the known antiviral agents in a short number of steps.

  DOI：

  10.1080/15257770600686279

文献信息

• An Economical Synthesis of Famciclovir
  作者：Toyoto Hijiya、Keizo Yamashita、Mitsuhiko Kojima、Yumiko Uchida、Satoshi Katayama、Takayoshi Torii、Hiroshi Shiragami、Kunisuke Izawa

  DOI：10.1080/15257779908041530

  日期：1999.4

  An economical synthesis of famciclovir from N-2-acetyl-7-benzylguanine by a novel regioselective alkylation with the diester cyclopropane compound was developed.
• Improved Industrial Syntheses of Penciclovir and Famciclovir Using N2-Acetyl-7-Benzylguanine and a Cyclic Side Chain Precursor
  作者：Takayoshi Torii、Keizo Yamashita、Mitsuhiko Kojima、Yumiko Suzuki、Toyoto Hijiya、Kunisuke Izawa

  DOI：10.1080/15257770600686279

  日期：2006.6

  We have established practical synthetic methods for penciclovir (PCV, 1) and famciclovir (FCV, 2) from N2-acetyl-7-benzylguanine (NAc7BnG, 3) and 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (4)-the latter being a more easily prepared cyclic precursor of the diacetate side chain (5) used in the conventional process. The coupling of 4 with 3 proceeded regioselectively at the N9 position of guanine in good yield. The coupling product was then successfully transformed into the known antiviral agents in a short number of steps.