5-(3-hydroxy-3-methylbutyn-1-yl)uracil | 893747-35-8

• 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-(3-hydroxy-3-methylbutyn-1-yl)uracil
• 英文别名: 5-(3-hydroxy-3-methylbut-1-ynyl)-1H-pyrimidine-2,4-dione
• CAS: 893747-35-8
• 化学式: C₉H₁₀N₂O₃
• mdl: MFCD06803807
• 分子量: 194.19
• InChiKey: DRTSROGXFJBMHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3-hydroxy-3-methylbutyn-1-yl)uracil 在 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 32.0h， 生成 3-dodecyl-6-[(1-hydroxy-1-methyl)ethyl]furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  An Efficient Alternative Route To 3,6-Disubstituted-Furo[2,3-d]Pyrimidin-2-One Analogues

  摘要：

  Copper(I)-catalyzed 5-endo-dig cyclizations of 5-(alkyn-1-yl)uracil derivatives had given poor yields of substituted furo[2, 3]pyrimidin-2-ones unless the uracil ring was substituted at N1 with alkyl or glycosyl groups. This limited flexibility for the synthesis of analogues with varied substituents at N3 and/or C6 of the furo[2, 3]pyrimidin-2-one core has been overcome with 5-(3-hydroxyalkyn-1-yl)uracil compounds with no substituent at N1. Manipulation of the side-chain hydroxyl group gives access to additional furo[2,3- d ]pyrimidin-2-one analogues.

  DOI：

  10.1080/10810730500265757
• 作为产物：
  描述：

  5-碘尿嘧啶 、 2-甲基-3-丁炔-2-醇 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以79%的产率得到5-(3-hydroxy-3-methylbutyn-1-yl)uracil
  参考文献：
  名称：

  An Efficient Alternative Route To 3,6-Disubstituted-Furo[2,3-d]Pyrimidin-2-One Analogues

  摘要：

  Copper(I)-catalyzed 5-endo-dig cyclizations of 5-(alkyn-1-yl)uracil derivatives had given poor yields of substituted furo[2, 3]pyrimidin-2-ones unless the uracil ring was substituted at N1 with alkyl or glycosyl groups. This limited flexibility for the synthesis of analogues with varied substituents at N3 and/or C6 of the furo[2, 3]pyrimidin-2-one core has been overcome with 5-(3-hydroxyalkyn-1-yl)uracil compounds with no substituent at N1. Manipulation of the side-chain hydroxyl group gives access to additional furo[2,3- d ]pyrimidin-2-one analogues.

  DOI：

  10.1080/10810730500265757

文献信息

• An Efficient Alternative Route To 3,6-Disubstituted-Furo[2,3-<i>d</i>]Pyrimidin-2-One Analogues
  作者：Zlatko Janeba、Noha Maklad、Morris J. Robins

  DOI：10.1080/10810730500265757

  日期：2005.9.1

  Copper(I)-catalyzed 5-endo-dig cyclizations of 5-(alkyn-1-yl)uracil derivatives had given poor yields of substituted furo[2, 3]pyrimidin-2-ones unless the uracil ring was substituted at N1 with alkyl or glycosyl groups. This limited flexibility for the synthesis of analogues with varied substituents at N3 and/or C6 of the furo[2, 3]pyrimidin-2-one core has been overcome with 5-(3-hydroxyalkyn-1-yl)uracil compounds with no substituent at N1. Manipulation of the side-chain hydroxyl group gives access to additional furo[2,3- d ]pyrimidin-2-one analogues.