5,5-difluoro-6-acetoxy-5,6-dihydrouracil | 100814-61-7

• 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: 5,5-difluoro-6-acetoxy-5,6-dihydrouracil
• 英文别名: (5,5-Difluoro-2,6-dioxo-1,3-diazinan-4-yl) acetate
• CAS: 100814-61-7
• 化学式: C₆H₆F₂N₂O₄
• 分子量: 208.121
• InChiKey: CNCUIJPPTZPCAT-UHFFFAOYSA-N

物化性质

• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  尿嘧啶 生成 5,5-difluoro-6-acetoxy-5,6-dihydrouracil
  参考文献：
  名称：

  VISSER, GERARD W. M.;HERDER, RENELLA E.;DE, KANTER FRANS J. J.;HERSCHELD,+, J. CHEM. SOC. PERKIN TRANS.,(1988) N 5, 1203-1207

  摘要：

  DOI：

文献信息

• Fluorination of uracil with acetylhypofluorite and fluorine in acetic acid: mechanistic investigation
  作者：Mirko Diksic、Slmin Farrokhzad、Lawrence D. Colebrook

  DOI：10.1139/v86-067

  日期：1986.2.1

  Fluorination of uracil with acetylhypofluorite and fluorine in acetic acid is described. The influence of the acetate ion on the products of the fluorination reaction was examined. Two stereoisomers (cis (3) and trans (4)) were found in the reaction mixture following fluorination in the absence of the acetate ion, but only one isomer (4) and 5-fluorouracil were found when the acetate ion was present during the fluorination reaction. ²H nuclear magnetic resonance revealed that acetate from the solution containing acetate ion rather than from the residue from acetylhypofluorite binds to position 6 of uracil to form intermediates. The synthesis yields 5-fluorouracil isolated as pure compound in a chemical yield, relative to the fluorine introduced, of about 45%. The influence of inorganic cations on the yield of acetylhypofluorite was also evaluated.

  用冰醋酸中的乙酰次氟酸酯和氟气对尿嘧啶进行氟化反应。考察了醋酸根离子对氟化反应产物的影响。在没有醋酸根离子存在的情况下进行氟化反应后，在反应混合物中发现了两种立体异构体（顺式（3）和反式（4）），但当氟化反应过程中存在醋酸根离子时，只发现了一种异构体（4）和5-氟尿嘧啶。2H核磁共振显示，来自含有醋酸根离子的溶液而不是来自乙酰次氟酸酯残留物的醋酸根离子与尿嘧啶的6位结合形成中间体。合成产率为约45％的5-氟尿嘧啶以纯化合物的形式分离。还评估了无机阳离子对乙酰次氟酸酯产率的影响。
• N-Fluorobis[(perfluoroalkyl)sulfonyl]imides: reactions with some olefins via .alpha.-fluoro carbocationic intermediates
  作者：Darryl D. DesMarteau、Ze Qi Xu、Michael Witz

  DOI：10.1021/jo00028a042

  日期：1992.1

  N-Fluorobis(perfluoroalkyl)sulfonyl]imides are a new class of electrophilic fluorinating agents. Reaction of (CF3SO2)2NF (1) with olefins gave various products, depending on the reaction conditions and the structure of the substrate. In solvents of higher nucleophilicity such as H2O, acetic acid, aqueous HCl, and (HF)(n)Py, alpha-fluorohydrins or their acetates, alpha,beta-chlorofluoro- and alpha,beta-difluoroalkanes were obtained. In acetic acid, trans-stilbene and tetraphenylethylene produced the rearranged, nonfluorinated aldehyde and ketone. Evidence is presented for the reactions proceeding via a one-electron transfer mechanism involving alpha-fluorocarbocationic intermediates.
• 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：——
• Mechanism and stereochemistry of the fluorination of uracil and cytosine using fluorine and acetyl hypofluorite
  作者：Gerard W. M. Visser、Saskia Boele、Bert W. Van Halteren、Gertrudis H. J. N. Knops、Jacobus D. M. Herscheid、Gerard A. Brinkman、Arend Hoekstra

  DOI：10.1021/jo00359a015

  日期：1986.5