<2-nitro-1-(2-oxytetrahydropyranyl)-propan-2-yl>cytosine

• 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: <2-nitro-1-(2-oxytetrahydropyranyl)-propan-2-yl>cytosine
• 英文别名: 4-Amino-1-[2-nitro-1-(oxan-2-yloxy)propan-2-yl]pyrimidin-2-one
• 化学式: C₁₂H₁₈N₄O₅
• 分子量: 298.299
• InChiKey: QMHBKNRQGZZBNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <2-nitro-1-(2-oxytetrahydropyranyl)-propan-2-yl>cytosine 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以95%的产率得到2-(N-1-cytosine)-2-nitropropanol
  参考文献：
  名称：

  Selective N1-Alkylation of Pyrimidine BasesviaRadical (SRN1) Mechanism

  摘要：

  Under photostimulated SRNI conditions the cytosine nitranion behaves as a nucleophile toward the carbon radical generated from gem halonitro, or gem dinitroalcane derivatives to give regiospecifically the N-1 alkyled cytosine compound which is representative of a new series of cytosine acyclonucleosides. Uracile and its 5-fluoro or 5-nitro analogs fail to react and thymine gives an unexpected disubstituted S(RN)1 product whose formation is discussed.

  DOI：

  10.1080/15257779408011887
• 作为产物：
  描述：

  胞嘧啶 、 (+/-)-2,2-dinitropropyl tetrahydropyranyl ether 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 13.0h， 以68%的产率得到<2-nitro-1-(2-oxytetrahydropyranyl)-propan-2-yl>cytosine
  参考文献：
  名称：

  Selective N1-Alkylation of Pyrimidine BasesviaRadical (SRN1) Mechanism

  摘要：

  Under photostimulated SRNI conditions the cytosine nitranion behaves as a nucleophile toward the carbon radical generated from gem halonitro, or gem dinitroalcane derivatives to give regiospecifically the N-1 alkyled cytosine compound which is representative of a new series of cytosine acyclonucleosides. Uracile and its 5-fluoro or 5-nitro analogs fail to react and thymine gives an unexpected disubstituted S(RN)1 product whose formation is discussed.

  DOI：

  10.1080/15257779408011887

文献信息

• Selective N1-Alkylation of Pyrimidine Bases<i>via</i>Radical (SRN1) Mechanism
  作者：Rachid Benhida、Tawfik Gharbaoui、Andre Lechevallier、Rene Beugelmans

  DOI：10.1080/15257779408011887

  日期：1994.6

  Under photostimulated SRNI conditions the cytosine nitranion behaves as a nucleophile toward the carbon radical generated from gem halonitro, or gem dinitroalcane derivatives to give regiospecifically the N-1 alkyled cytosine compound which is representative of a new series of cytosine acyclonucleosides. Uracile and its 5-fluoro or 5-nitro analogs fail to react and thymine gives an unexpected disubstituted S(RN)1 product whose formation is discussed.