9-(2-tert-butoxycarbonylethyl)adenine | 223409-15-2

• 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-(2-tert-butoxycarbonylethyl)adenine
• 英文别名: Tert-butyl 3-(6-aminopurin-9-yl)propanoate
• CAS: 223409-15-2
• 化学式: C₁₂H₁₇N₅O₂
• mdl: MFCD25961200
• 分子量: 263.299
• InChiKey: KUXPXDYTZPCWMY-UHFFFAOYSA-N

物化性质

• 沸点：
  458.1±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(2-tert-butoxycarbonylethyl)adenine 在 盐酸 、 sodium tetrahydroborate 、 magnesium ethylate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 乙酸乙酯 为溶剂， 反应 52.0h， 生成 N⁶-benzoyl-9-(4-ethoxycarbonyl-3-hydroxobutyl)adenine
  参考文献：
  名称：

  无环卡巴核苷膦酸酯的合成，天然脱氧核糖核苷酸的结构类似物

  摘要：

  已从 DNA 核碱基和丙烯酸叔丁酯开始制备了以天然脱氧核糖核苷酸为模型的无环卡巴核苷膦酸酯。从迈克尔型反应获得的产物被延长为 β-氧代酯，该酯首先被还原为 β-羟基酯，然后转化为受保护的 β-羟基醛。Wittig-Horner-Emmons 与亚甲基双膦酸四异丙酯的阴离子反应，去保护后得到所需的 4-羟基-6-嘌呤基-或-6-嘧啶基-1-己烯基膦酸。还制备了一种二聚体，一种与 DNA 同形的无环多核苷酸 (APN) 的潜在前体。

  DOI：

  10.1002/(sici)1099-0690(199904)1999:4<931::aid-ejoc931>3.0.co;2-r
• 作为产物：
  描述：

  丙烯酸叔丁酯 、 腺嘌呤 在 三乙烯二胺 、 四丁基溴化铵 作用下， 反应 0.13h， 以71%的产率得到9-(2-tert-butoxycarbonylethyl)adenine
  参考文献：
  名称：

  Microwave-Promoted Michael Addition of Azaheterocycles to α,β-Unsaturat­ed Esters and Acid under Solvent-Free Conditions

  摘要：

  Regioselective Michael addition of N-9 adenine to ethyl acrylate under microwave activation in solid-liquid solvent-free phase-transfer catalysis using TBAB as catalyst and DABCO as base was extended to tert-butyl acrylate and acrylic acid. Under these conditions and in the presence of a catalytic amount of KOH, first Michael addition of indole and indolylmaleimide to acrylates is also reported.

  DOI：

  10.1055/s-0031-1290164

文献信息

• Pleuromutilin derivatives having a purine ring. Part 1: New compounds with promising antibacterial activity against resistant Gram-positive pathogens
  作者：Yoshimi Hirokawa、Hironori Kinoshita、Tomoyuki Tanaka、Takanori Nakamura、Koichi Fujimoto、Shigeki Kashimoto、Tsuyoshi Kojima、Shiro Kato

  DOI：10.1016/j.bmcl.2008.05.011

  日期：2008.6

  In the course of our research aimed at the discovery of metabolic stable pleuromutilin derivatives with more potent antibacterial activity against Gram-positive pathogens than previous analogues, a series of compounds bearing a purine ring were prepared and evaluated. From SAR studies, we identified two promising compounds 85 and 87, which have excellent in vitro activity against a number of Gram-positive pathogens, including existing drug-resistant strains, and potent in vivo efficacy. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Acyclic Carba-Nucleoside Phosphonates, Structural Analogues to Natural Deoxyribonucleotides
  作者：Annamaria Esposito、Maria Grazia Perino、Maurizio Taddei

  DOI：10.1002/(sici)1099-0690(199904)1999:4<931::aid-ejoc931>3.0.co;2-r

  日期：1999.4

  reaction were elongated to β-oxo esters that were first reduced to β-hydroxy esters and then transformed into protected β-hydroxy aldehydes. Wittig–Horner–Emmons reaction with the anion of tetraisopropyl methylenebisphosphonate gave, after deprotection, the desired 4-hydroxy-6-purinyl- or -6-pyrimidinyl-1-hexenylphosphonic acids. A dimer, potential precursor of acyclic polynucleotides (APN), homomorphous with

  已从 DNA 核碱基和丙烯酸叔丁酯开始制备了以天然脱氧核糖核苷酸为模型的无环卡巴核苷膦酸酯。从迈克尔型反应获得的产物被延长为 β-氧代酯，该酯首先被还原为 β-羟基酯，然后转化为受保护的 β-羟基醛。Wittig-Horner-Emmons 与亚甲基双膦酸四异丙酯的阴离子反应，去保护后得到所需的 4-羟基-6-嘌呤基-或-6-嘧啶基-1-己烯基膦酸。还制备了一种二聚体，一种与 DNA 同形的无环多核苷酸 (APN) 的潜在前体。
• Microwave-Promoted Michael Addition of Azaheterocycles to α,β-Unsaturat­ed Esters and Acid under Solvent-Free Conditions
  作者：Isabelle McCort-Tranchepain、Lilian Dubois、Francine Acher

  DOI：10.1055/s-0031-1290164

  日期：2012.3

  Regioselective Michael addition of N-9 adenine to ethyl acrylate under microwave activation in solid-liquid solvent-free phase-transfer catalysis using TBAB as catalyst and DABCO as base was extended to tert-butyl acrylate and acrylic acid. Under these conditions and in the presence of a catalytic amount of KOH, first Michael addition of indole and indolylmaleimide to acrylates is also reported.