1-(2,5-Dihydrofur-2-yl)-uracil | 65361-14-0

• 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: 1-(2,5-Dihydrofur-2-yl)-uracil
• 英文别名: 1-(2,3-dihydrofuran-5-yl)uracil；1-(2,5-Dihydrofuran-2-yl)pyrimidine-2,4-dione；1-(2,5-dihydrofuran-2-yl)pyrimidine-2,4-dione
• CAS: 65361-14-0
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: CEVRKBKMYPQPHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 碘苯二乙酸 、 2,4-二(三甲硅氧基)嘧啶 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以8.9%的产率得到(2R,6S)-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-one
  参考文献：
  名称：

  A New Route to N1-Substituted Uracil Derivatives Using Hypervalent Iodine

  摘要：

  In continuation of our previous study, oxidative coupling reactions of uracil with allylsilane or enol ethers were examined using diacetoxyiodobenzene. The reaction of persilylated uracil with 3,4-dihydro-2H-pyran in the presence of TMSOTf and PhI(OAc)(2) resulted in the formation of a dihydropyranyluracil derivative, although the yield was low. In an extension of the oxidative coupling reaction, a novel glycosylation reaction using glycal derivatives as substrates was also developed. The treatment of persilylated uracil and 3,4-dihydro-2H-pyran with (PhSe)(2) and PhI(OAc)(2) in the presence of a catalytic amount of TMSOTf gave a 2,3-anti-derivative of 1-(3-phenylselanyltetrahydropyran-2-yl) uracil stereoselectively and in good yield.

  DOI：

  10.1055/s-0031-1290749

文献信息

• A New Route to N1-Substituted Uracil Derivatives Using Hypervalent Iodine
  作者：Yuichi Yoshimura、Hiroki Takahata、Hiroya Kan-no、Y. Kiran、Yoshihiro Natori、Yukako Saito

  DOI：10.1055/s-0031-1290749

  日期：2012.4

  In continuation of our previous study, oxidative coupling reactions of uracil with allylsilane or enol ethers were examined using diacetoxyiodobenzene. The reaction of persilylated uracil with 3,4-dihydro-2H-pyran in the presence of TMSOTf and PhI(OAc)(2) resulted in the formation of a dihydropyranyluracil derivative, although the yield was low. In an extension of the oxidative coupling reaction, a novel glycosylation reaction using glycal derivatives as substrates was also developed. The treatment of persilylated uracil and 3,4-dihydro-2H-pyran with (PhSe)(2) and PhI(OAc)(2) in the presence of a catalytic amount of TMSOTf gave a 2,3-anti-derivative of 1-(3-phenylselanyltetrahydropyran-2-yl) uracil stereoselectively and in good yield.