1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-(1,2,4-triazolo)-5-(2-chloroethyl)pyrimidin-2(1H)-one | 126164-58-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-(1,2,4-triazolo)-5-(2-chloroethyl)pyrimidin-2(1H)-one
• 英文别名: [(2R,3S,5R)-3-acetyloxy-5-[5-(2-chloroethyl)-2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 126164-58-7
• 化学式: C₁₇H₂₀ClN₅O₆
• 分子量: 425.829
• InChiKey: BHRQBUXADFITCK-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-(1,2,4-triazolo)-5-(2-chloroethyl)pyrimidin-2(1H)-one 在 吡啶 、 sodium methylate 、 肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.83h， 生成 2-methyl-8-(2-chloroethyl)-6-(2-deoxy-β-D-erythro-pentofuranosyl)<1,2,4>triazolo<1,5-c>pyrimidin-5(6H)-one
  参考文献：
  名称：

  Loakes, David; Brown, Daniel M.; Salisbury, Stephen A., Journal of the Chemical Society. Perkin transactions I, 1999, # 10, p. 1333 - 1337

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(2-chloroethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-1H,3H-pyrimidine-2,4-dione 、 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[5-(2-chloro-ethyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-(1,2,4-triazolo)-5-(2-chloroethyl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  The Synthesis of BicyclicN4-Amino-2′-deoxycytidine Derivatives

  摘要：

  Nucleosides which have ambivalent tautomeric properties have value in a variety of nucleic acid hybridization applications, and as mutagenic agents. We describe here synthetic studies directed to stable derivatives of this kind of nucleoside based on N-4-aminocytosine. Treatment of the 4-(1H-1,2,4-triazol-1-yl)-5-(chloroethyl)pyrimidinone nucleoside derivative 5 with hydrazine leads to formation of the 6,6-bicyclic pyrimido-pyridazin-7-one 3, and with methylhydrazine to the corresponding fixed tautomeric I-methyl derivative 7 (Scheme 1). If these cyclization reactions are carried out in the presence of a base, the 6-ring bicyclic derivatives undergo rearrangement to their corresponding 5-ring pyrrolo-pyrimidin-2-one analogues 8 (Scheme 2). In the reaction of the triazolyl derivative 5 with 1-[(benzyloxy)carbonyl]-2-methylhydrazine, spontaneous cyclization gives the 5-ring derivative 13 related to 8 rather than the open-chain product 12 (Scheme 4). Reaction of an acetylated analogue of triazolyl derivative 5 with 1,1-dimethylhydrazine gives rise to some of the open-chain product 9, but it too cyclizes to a product that we have assigned the structure of the 6,6-ring quaternary ammonium salt 11 (Scheme 3).

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<2028::aid-hlca2028>3.0.co;2-e

文献信息

• The Synthesis of Bicyclic N4-Amino-2'-deoxycytidine Derivatives
  作者：D. Loakes、D. M. Brown

  DOI：10.1080/15257779508012364

  日期：1995.5.1