(5R,6S)-5-氟-6-羟基二氢-2,4(1H,3H)-嘧啶二酮 | 37103-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: (5R,6S)-5-氟-6-羟基二氢-2,4(1H,3H)-嘧啶二酮
• 英文名称: (+/-)-cis-5-Fluor-6-hydroxy-5,6-dihydrouracil
• 英文别名: (5R,6S)-5-fluoro-6-hydroxy-1,3-diazinane-2,4-dione
• CAS: 37103-91-6；93713-25-8；93713-26-9
• 化学式: C₄H₅FN₂O₃
• 分子量: 148.094
• InChiKey: AWONXBGDFDRWRH-NCGGTJAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S36/37,S45
• 危险类别码：
  R23/24/25
• 海关编码：
  2933599090
• 危险品运输编号：
  UN 2811

反应信息

• 作为产物：
  描述：

  5-氟脲嘧啶 、 水 生成 (5R,6S)-5-氟-6-羟基二氢-2,4(1H,3H)-嘧啶二酮
  参考文献：
  名称：

  ZUPANCIC, N.;ZUPAN, M.;SKET, B., J. FLUOR. CHEM., 1983, 23, N 5, 483

  摘要：

  DOI：

文献信息

• Regio and stereospecifity of solvent photoaddition to 5-fluorouracil and 1,3-dimethyl-5-fluorouracil
  作者：Nataša Zupančič、Marko Zupan、Boris Šket

  DOI：10.1135/cccc19841592

  日期：——

  Irradiation of 1,3-dimethyl-5-fluorouracil in methanol, ethanol, water and acetic acid, and 5-fluorouracil in water at λ = 253.7 nm resulted in the formation of two addition products. Regiospecifity was in all cases the same with functionalization at position 6 while the stereochemistry of addition dependend on the solvent. In water preferential trans addition proceeded while in acetic acid cis addition was predominant. Photoconversion of starting material was also twofold increased in acetic acid, compared to that in water.

  在甲醇、乙醇、水和乙酸中，以及在水中以λ = 253.7 nm照射1,3-二甲基-5-氟尿嘧啶和5-氟尿嘧啶，结果形成了两种加成产物。在所有情况下，区域特异性都相同，以在6位处进行官能化。而加成的立体化学则取决于溶剂。在水中，有选择性的进行顺式加成，而在乙酸中，顺式加成则是主要的。与水相比，起始物质在乙酸中的光转换也增加了两倍。
• A Convenient Synthesis of 5-Fluoropyrimidines Using 1-(Chloromethyl)-4-fluoro-1,4-diazabicyclo[2.cntdot.2.cntdot.2]octane Bis(tetrafluoroborate)-SELECTFLUOR Reagent
  作者：G. Sankar Lal、W. Pastore、R. Pesaresi

  DOI：10.1021/jo00127a046

  日期：1995.11

  The pyrimidine bases uracil and thymine react with the titled reagent in water to generate the corresponding fluorohydrins. Uracil fluorohydrin provides 5-fluorouracil on sublimation. Triacetyluridine reacts similarly in the presence of H2O, AcOH, or MeOH to form the respective adducts from which 5-fluorotriacetyluridine was obtained. The fluorohydrin of diacetylthymidine and the difluoromethoxy derivative of triacetylcytidine were also obtained by reaction of the nucleosides with 1-(chloromethyl)-4-fluoro-1,4-diazobicyclo[2.2.2]octane bis(tetrafluoroborate)-SELECTFLUOR in H2O and MeOH, respectively. This method represents a new practical and direct route to 5-fluoropyrimidine nucleoside.
• Visser, W. M. Gerard; Herder, E. Renella; Kanter, Frans J. J. de, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1203 - 1208
  作者：Visser, W. M. Gerard、Herder, E. Renella、Kanter, Frans J. J. de、Herscheid D. M. Jacobus

  DOI：——

  日期：——
• ZUPANCIC, N.;ZUPAN, M.;SKET, B., COLLECT. CZECHOSL. CHEM. COMMUN., 1984, 49, N 7, 1592-1599
  作者：ZUPANCIC, N.、ZUPAN, M.、SKET, B.

  DOI：——

  日期：——