N²-acetyl-O⁶-2-(4-nitrophenyl)ethylguanine | 218152-30-8

• 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-acetyl-O⁶-2-(4-nitrophenyl)ethylguanine
• 英文别名: N²-acetyl-O⁶-(2-(p-nitrophenyl)ethyl)guanine；N-[6-[2-(4-nitrophenyl)ethoxy]-7H-purin-2-yl]acetamide
• CAS: 218152-30-8
• 化学式: C₁₅H₁₄N₆O₄
• 分子量: 342.314
• InChiKey: BKMMTHLDYOLBFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  275-277 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²-acetyl-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 、 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 、 甲苯 为溶剂， 反应 222.0h， 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 水 、 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 3.0h， 生成 N²-acetyl-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

• Synthesis by conjugate radical addition of new heterocyclic amino acids with nucleobase side chains
  作者：Raymond C.F Jones、Didier J.C Berthelot、James N Iley

  DOI：10.1016/s0040-4020(01)00546-4

  日期：2001.7

  N-(2-iodoethyl) and N-(3-iodopropyl)pyrimidines and purines undergo stereoselective conjugate radical addition with an optically active oxazolidinone acceptor to give syn-adducts that can be converted into amino acids carrying pyrimidine and purine (nucleobase) side chains.

  N-（2-碘乙基）和N-（3-碘丙基）嘧啶和嘌呤与光学活性的恶唑烷酮受体进行立体选择共轭基团加成，生成顺式加合物，可将其转化为带有嘧啶和嘌呤（核碱基）侧链的氨基酸。
• A convenient synthesis of racemic 2′-deoxy carbocyclic thymidines lacking the 5′-methylene group
  作者：Jinglan Zhou、Philip B. Shevlin

  DOI：10.1016/s0040-4039(98)01929-7

  日期：1998.11

  A convenient synthesis of racemic 2′-deoxy carbocyclic thymidines lacking the 5′-methylene group is reported. Thus, appropriately protected nucleic acid bases are coupled to 3-cyclopentenol, 1, via the Mitsunobu reaction. Epoxidation of the protected thymine substituted cyclopentene gives the corresponding syn and anti-epoxides in a 4:1 ratio. Ring opening of the syn-epoxide by a variety of nucleophiles

  报道了缺少5'-亚甲基的外消旋2'-脱氧碳环胸苷的方便合成。因此，通过Mitsunobu反应将适当保护的核酸碱基与3-环戊烯醇1偶联。被保护的胸腺嘧啶取代的环戊烯的环氧化以4：1的比例得到相应的顺式和反式环氧化物。多种亲核试剂使顺环氧化物开环导致缺少5'-亚甲基的外消旋2'-脱氧碳环胸苷。
• Synthesis by conjugate radical addition of new heterocyclic amino acids with nucleic acid bases in their side chains
  作者：Raymond C. F. Jones、Didier J. C. Berthelot、James N. Iley

  DOI：10.1039/b006843h

  日期：——

  N-(2-Iodoethyl) and N-(3-iodopropyl)pyrimidines and purines undergo stereoselective conjugate radical addition with an optically active oxazolidinone acceptor to give syn-adducts that can be converted into pyrimidine and purine amino acids.

  N-(2-碘乙基) 和 N-(3-碘丙基) 嘧啶和嘌呤与光学活性恶唑烷酮受体发生立体选择性共轭自由基加成反应，得到可转化为嘧啶和嘌呤氨基酸的顺式加合物。
• Synthesis of N -Boc and N -Fmoc dipeptoids with nucleobase residues as peptoid nucleic acid monomers
  作者：Yun Wu、Jie-Cheng Xu、Jing Liu、You-Xing Jin

  DOI：10.1016/s0040-4020(01)00182-x

  日期：2001.4

  synthesis of Boc and Fmoc protected peptoid nucleic acid monomers bearing thymine (4a, 4b), adenine (6a, 6b) or guanine (7a, 7b) on the side chain is described. These nucleobases were attached to the amino group of glycine via an ethylene linkage using the Mitsunobu reaction, except cytosine, which was attached using alkylation. After deprotection, these amino acids have been used for synthesizing N-Boc

  描述了在侧链上带有胸腺嘧啶（4a，4b），腺嘌呤（6a，6b）或鸟嘌呤（7a，7b）的Boc和Fmoc保护的类肽核酸单体的合成。这些核碱基通过Mitsunobu反应通过乙烯键连接到甘氨酸的氨基上，但胞嘧啶除外，胞嘧啶通过烷基化连接。脱保护后，这些氨基酸已用于合成N -Boc和N -Fmoc二肽。