trans-5-fluoro-6-methoxy-1,3-dimethyl-5,6-dihydrouracil | 4097-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: trans-5-fluoro-6-methoxy-1,3-dimethyl-5,6-dihydrouracil
• 英文别名: (5R,6R)-5-fluoro-6-methoxy-1,3-dimethyl-1,3-diazinane-2,4-dione
• CAS: 4097-24-9；87498-30-4；87498-31-5
• 化学式: C₇H₁₁FN₂O₃
• 分子量: 190.174
• InChiKey: JSNNJZPPZOHUHB-UJURSFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.18
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.85
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,3-二甲基-5-氟尿嘧啶 、 甲醇 生成 trans-5-fluoro-6-methoxy-1,3-dimethyl-5,6-dihydrouracil
  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

• Room-temperature reactions of CsSO4F with organic molecules containing heteroatoms
  作者：Stojan Stavber、Marko Zupan

  DOI：10.1039/c39830000563

  日期：——

  Room-temperature fluorination of pentane-2,4-dione with CsSO4F gave 3-fluoro and 1,3-difluoro derivatives, while 5,5-difluorobarbituric acid was formed in high yield in a 2 h reaction at 100 °C; 1,3-dimethyluracil was converted in methanol via cis- and trans-5-fluoro-6-methoxy derivatives into 5-fluoro-1,3-dimethyluracil in high yield and uridine into 5-fluorouridine.

  用CsSO 4 F在室温下氟化戊烷-2,4-二酮可得到3-氟和1,3-二氟衍生物，而在100°C的2 h反应中高产率形成5,5-二氟巴比妥酸；1,3-二甲基尿嘧啶在甲醇中通过顺式和反式-5-氟-6-甲氧基衍生物高产率转化为5-氟-1,3-二甲基尿嘧啶，尿苷转化为5-氟尿苷。
• Mild fluorination of uracil derivatives by caesium fluoroxysulphate
  作者：Stojan Stavber、Marko Zupan

  DOI：10.1016/s0040-4020(01)88400-3

  日期：1990.1

  3-dimethyl-5-halo substituted uracil derivatives reacted with CsSO4F under mild reaction conditions. Reactions carried out in an acetonitrile/water mixture or in a wide range of alcohols (methanol, ethanol, isopropanol and tert.butanol) resulted in the regioselective formation of the 5-fluoro-6-hydroxy or 5-fluoro-6-alkoxy-1,3-dimethyl-5,6-dihydrouracil derivatives, respectively, while the stereochemistry

  1,3-二甲基和1,3-二甲基-5-卤代尿嘧啶衍生物在温和的反应条件下与CsSO 4 F反应。在乙腈/水混合物或多种醇（甲醇，乙醇，异丙醇和叔丁醇）中进行的反应会导致区域选择性形成5-氟-6-羟基或5-氟-6-烷氧基- 1,3-二甲基-5,6-二氢尿嘧啶衍生物，而反应的立体化学是强烈同位的。尿嘧啶转化为5-氟尿嘧啶，尿苷转化为5-氟尿苷，而巴比妥酸与作为溶剂的乙腈中的CsSO 4 F反应生成5,5-二氟巴比妥酸。
• Regio and stereospecificity of solvent photoaddition to 5-fluorouracil and 1,3-dimethyl-5-fluorouracil
  作者：N. Zupančič、M. Zupan、B. Šket

  DOI：10.1016/s0022-1139(00)85556-6

  日期：1983.11

  3-dimethyl-5-fluorouracil in methanol, ethanol, water, and acetic acid, and 5-fluorouracil in water at 253.7nm 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 depended on the solvent. In water preferential trans addition proceeded, while in acetic acid cis addition was predominant. Photoconversion

  在253.7nm的甲醇，乙醇，水和乙酸中照射1,3-二甲基-5-氟尿嘧啶，在水中照射5-氟尿嘧啶，导致形成两种加成产物。在所有情况下，区域专一性都相同，在6位具有官能化，而添加的立体化学取决于溶剂。在水中优先进行反式添加，而在乙酸中主要进行顺式添加。与水中相比，凝视物质的光转化在乙酸中的含量也增加了两倍。
• 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。
• 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：——