5-(3-hydroxyprop-1yn-1-yl)pyrimidin-2,4-dione | 570409-74-4

• 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-hydroxyprop-1yn-1-yl)pyrimidin-2,4-dione
• 英文别名: 5-(3-hydroxypropyn-1-yl)uracil；5-(3-hydroxyprop-1-ynyl)-1,3-dihydropyrimidine-2,4-dione；5-(3-hydroxyprop-1-ynyl)-1H-pyrimidine-2,4-dione
• CAS: 570409-74-4
• 化学式: C₇H₆N₂O₃
• mdl: MFCD06803805
• 分子量: 166.136
• InChiKey: QQUDYGFTJFEYEA-UHFFFAOYSA-N

物化性质

• 熔点：
  >200 °C (decomp)(Solv: ethanol (64-17-5))
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 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-hydroxyprop-1yn-1-yl)pyrimidin-2,4-dione 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 2-hexyloxy-6-(hydroxymethyl)furo[2,3-d]pyrimidine
  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-丙炔-1-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89%的产率得到5-(3-hydroxyprop-1yn-1-yl)pyrimidin-2,4-dione
  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

• Fluorescent probes for DNA detection by hybridization with improved sensitivity and low background
  申请人：Lokhov Sergey

  公开号：US20050214797A1

  公开（公告）日：2005-09-29

  Minor groove binder-oligonucleotide probes are provided along with methods for their use wherein the probes have an attached fluorophore which, in an unhybridized form exhibits very low background signal.

  提供了与其使用方法一起的小沟结合物-寡核苷酸探针，其中这些探针带有一个附加的荧光物质，未杂交形式下显示出非常低的背景信号。
• FUNCTIONALIZED 3-ALKYNYL PYRAZOLOPYRIMIDINE ANALOGUES AS UNIVERSAL BASES AND METHODS OF USE
  申请人：Vorobiev Alexei

  公开号：US20130261014A1

  公开（公告）日：2013-10-03

  3-alkynyl inosine analogs and their uses as universal bases are provided. The inosine analogues can be incorporated into nucleic acid primers and probes. They do not significantly destabilize nucleic acid duplexes. As a result, the novel nucleic acid primers and probes incorporating the inosine analogues can be used in a variety of methods. The analogs function unexpectedly well as universal bases. Not only do they stabilize duplexes substantially more than hypoxanthine opposite A, C, T, and G but they are also recognized in primers by polymerases, allowing efficient amplification.

  提供了3-炔基肌苷类似物及其作为通用碱基的用途。这些肌苷类似物可以被合并到核酸引物和探针中。它们不会显著破坏核酸双链。因此，包含这些肌苷类似物的新型核酸引物和探针可以用于各种方法。这些类似物意外地作为通用碱基发挥良好作用。它们不仅比嘌呤对A、C、T和G稳定双链更多，而且在引物中被聚合酶识别，从而实现高效扩增。
• Real-time linear detection probes: sensitive 5'-minor groove binder-containing probes for PCR analysis
  申请人：Epoch Biosciences, Inc.

  公开号：US20030175728A1

  公开（公告）日：2003-09-18

  Oligonucleotide probes/conjugates are provided along with method for their use in assays to monitor amplification wherein the signal produced does not rely on 5′ nuclease digestion.

  提供了寡核苷酸探针/共轭物，并提供了它们在检测扩增过程中的使用方法，其中产生的信号不依赖于5'核酸酶消化。
• TMLEVELING METHODS
  申请人：Epoch Biosciences, Inc.

  公开号：US20030224359A1

  公开（公告）日：2003-12-04

  Modified oligonucleotides are provided containing bases selected from unsubstituted and 3-substituted pyrazolo[3,4-d]pyrimidines and 5-substituted pyrimidines, and optionally have attached minor groove binders and reporter groups.

  提供了改性寡核苷酸，其中包含选择自未取代和3-取代的吡唑并[3,4-d]嘧啶和5-取代嘧啶的碱基，并且可选择附加次级沟结合剂和报告分子。
• Tm leveling compositions
  申请人：Dempcy O. Robert

  公开号：US20060003349A1

  公开（公告）日：2006-01-05

  Modified oligonucleotides are provided containing bases selected from unsubstituted and 3-substituted pyrazolo[3,4-d]pyrimidines and 5-substituted pyrimidines, and optionally have attached minor groove binders and reporter groups.

  提供了修饰的寡核苷酸，其中包含从未置换和3-置换的吡唑并[3,4-d]嘧啶和5-置换的嘧啶中选择的碱基，并且可选择附加小沟结合剂和报告基团。