1-(2-deoxy-3-methylxanthyl-β-D-ribofuramnosyl)thymine | 147138-38-3

• 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-(2-deoxy-3-methylxanthyl-β-D-ribofuramnosyl)thymine
• 英文别名: O-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-3-yl] methylsulfanylmethanethioate；O-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] methylsulfanylmethanethioate
• CAS: 147138-38-3
• 化学式: C₁₂H₁₆N₂O₅S₂
• 分子量: 332.401
• InChiKey: JLOUHCVDFVBVOM-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-3-methylxanthyl-β-D-ribofuramnosyl)thymine 在 吡啶 、 N-碘代丁二酰亚胺 、 氢氟酸 、 氨 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 1-(2-deoxy-3-O-trifluoromethyl-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Determination of the Group Electronegativity of CF₃Group in 3′-O-CF₃-Thymidine by¹-NMR

  摘要：

  The interplay of enthalpy of the gauche effect (Delta H degrees(GE)) Of the [X3'-C3'-C4'-O4'] fragment in various 3'-substituted (X) 2',3'-dideoxythymidine derivatives 1 - 7 and the inherent anomeric effect drives the two-state North reversible arrow South equilibrium in the constituent sugar moiety. The group electronegativity of 3'-OCF3 substituent in Marriott's, Inamoto's and Mullay's scales has been determined from simple calibration graphs correlating the group electronegativity of various 3'-substituents (X) in 2',3'-dideoxythymidine derivatives 1 - 7 with the experimental strength (Delta H degrees(GE)) Of the [X3'-C3'-C4'-O4'] gauche effect. Delta H degrees(GE) has been experimentally determined from pseudorotationaI analyses of temperature-dependent (3)J(HH) coupling constants, and can be used as an unambiguous tool for direct experimental estimation of the group electronegativity of a specific substituent covalently attached to 3'-carbon of 2',3'-dideoxythymidine, which can be compared, in turn, with the theoretical estimation carried out according to Marriott's or Inamotols procedure. Inconsistency found between theoretical values in Marriott's and Inamoto's scales, on the one hand, and between our experimental estimate and the theoretical value in Marriott's scale, on the other, have been solved by refining the electronegativity scale using our experimental data for 1 - 7.

  DOI：

  10.1080/15257779908041642
• 作为产物：
  描述：

  5'-O-tritylthymidine 在 sodium hydroxide 、 四丁基溴化铵 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 1-(2-deoxy-3-methylxanthyl-β-D-ribofuramnosyl)thymine
  参考文献：
  名称：

  Determination of the Group Electronegativity of CF₃Group in 3′-O-CF₃-Thymidine by¹-NMR

  摘要：

  The interplay of enthalpy of the gauche effect (Delta H degrees(GE)) Of the [X3'-C3'-C4'-O4'] fragment in various 3'-substituted (X) 2',3'-dideoxythymidine derivatives 1 - 7 and the inherent anomeric effect drives the two-state North reversible arrow South equilibrium in the constituent sugar moiety. The group electronegativity of 3'-OCF3 substituent in Marriott's, Inamoto's and Mullay's scales has been determined from simple calibration graphs correlating the group electronegativity of various 3'-substituents (X) in 2',3'-dideoxythymidine derivatives 1 - 7 with the experimental strength (Delta H degrees(GE)) Of the [X3'-C3'-C4'-O4'] gauche effect. Delta H degrees(GE) has been experimentally determined from pseudorotationaI analyses of temperature-dependent (3)J(HH) coupling constants, and can be used as an unambiguous tool for direct experimental estimation of the group electronegativity of a specific substituent covalently attached to 3'-carbon of 2',3'-dideoxythymidine, which can be compared, in turn, with the theoretical estimation carried out according to Marriott's or Inamotols procedure. Inconsistency found between theoretical values in Marriott's and Inamoto's scales, on the one hand, and between our experimental estimate and the theoretical value in Marriott's scale, on the other, have been solved by refining the electronegativity scale using our experimental data for 1 - 7.

  DOI：

  10.1080/15257779908041642

文献信息

• Determination of the Group Electronegativity of CF₃Group in 3′-<i>O</i>-CF₃-Thymidine by¹-NMR
  作者：C. Thibaudeau、N. Nishizono、Y. Sumita、A. Matsuda、J. Chattopadhyaya

  DOI：10.1080/15257779908041642

  日期：1999.4

  The interplay of enthalpy of the gauche effect (Delta H degrees(GE)) Of the [X3'-C3'-C4'-O4'] fragment in various 3'-substituted (X) 2',3'-dideoxythymidine derivatives 1 - 7 and the inherent anomeric effect drives the two-state North reversible arrow South equilibrium in the constituent sugar moiety. The group electronegativity of 3'-OCF3 substituent in Marriott's, Inamoto's and Mullay's scales has been determined from simple calibration graphs correlating the group electronegativity of various 3'-substituents (X) in 2',3'-dideoxythymidine derivatives 1 - 7 with the experimental strength (Delta H degrees(GE)) Of the [X3'-C3'-C4'-O4'] gauche effect. Delta H degrees(GE) has been experimentally determined from pseudorotationaI analyses of temperature-dependent (3)J(HH) coupling constants, and can be used as an unambiguous tool for direct experimental estimation of the group electronegativity of a specific substituent covalently attached to 3'-carbon of 2',3'-dideoxythymidine, which can be compared, in turn, with the theoretical estimation carried out according to Marriott's or Inamotols procedure. Inconsistency found between theoretical values in Marriott's and Inamoto's scales, on the one hand, and between our experimental estimate and the theoretical value in Marriott's scale, on the other, have been solved by refining the electronegativity scale using our experimental data for 1 - 7.