N²,N⁹-diacetyl-O⁶-2-(4-nitrophenyl)ethylguanine | 917376-69-3

• 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: N²,N⁹-diacetyl-O⁶-2-(4-nitrophenyl)ethylguanine
• 英文别名: 9,N²-diacetyl-O⁶-(2-(p-nitrophenyl)ethyl)guanine；N-{9-Acetyl-6-[2-(4-nitrophenyl)ethoxy]-9H-purin-2-yl}acetamide；N-[9-acetyl-6-[2-(4-nitrophenyl)ethoxy]purin-2-yl]acetamide
• CAS: 917376-69-3
• 化学式: C₁₇H₁₆N₆O₅
• 分子量: 384.351
• InChiKey: SPAQWPBFMDLLDM-UHFFFAOYSA-N

物化性质

• 熔点：
  215-219 °C(Solv: ethyl ether (60-29-7))
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N²,N⁹-diacetyl-O⁶-2-(4-nitrophenyl)ethylguanine 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 trimethylsilyl trifluorosulfonate 、 四丁基氟化铵 、 氨 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 226.0h， 生成 O6-[2-(4-nitrophenyl)ethyl]-N2-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine
  参考文献：
  名称：

  Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides

  摘要：

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.

  DOI：

  10.1080/15257770500267113
• 作为产物：
  描述：

  鸟嘌呤 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N²,N⁹-diacetyl-O⁶-2-(4-nitrophenyl)ethylguanine
  参考文献：
  名称：

  N2-乙酰基-O6-(2-(对硝基苯基)乙基)鸟嘌呤：合成 9-取代鸟嘌呤衍生物的便捷构件

  摘要：

  摘要 容易获得的 N2-乙酰基-O6-(2-(对硝基苯基)乙基)鸟嘌呤可以与伯醇或仲醇发生光延反应，生成鸟嘌呤衍生物。X 射线数据表明仅形成了所需的 9-取代鸟嘌呤衍生物。

  DOI：

  10.1080/00397919908086475

文献信息

• N²-Acetyl-O⁶-(2-(P-Nitrophenyl)Ethyl)Guanine: A Convenient Building Block for the Synthesis of 9-Substituted Guanine Derivatives
  作者：Jinglan Zhou、Jui-Yi Tsai、Kamal Bouhadir、Philip B. Shevlin

  DOI：10.1080/00397919908086475

  日期：1999.9

  Abstract Readily accessible N2-acetyl-O6-(2-(p-nitrophenyl)ethyl)guanine can undergo Mitsunobu reactions with either a primary or secondary alcohol to generate guanine derivatives. X-ray data indicates that only the desired 9-subsituted derivatives of guanine are formed.

  摘要 容易获得的 N2-乙酰基-O6-(2-(对硝基苯基)乙基)鸟嘌呤可以与伯醇或仲醇发生光延反应，生成鸟嘌呤衍生物。X 射线数据表明仅形成了所需的 9-取代鸟嘌呤衍生物。
• Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides
  作者：Christoph Henke、Wolfgang Pfleiderer

  DOI：10.1080/15257770500267113

  日期：2005.9.1

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.