(1'S,2'R)-1-<2-(Hydroxymethyl)cyclopropyl>uracil | 171032-47-6

• 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'S,2'R)-1-<2-(Hydroxymethyl)cyclopropyl>uracil
• 英文别名: 1-[(1S,2R)-2-(hydroxymethyl)cyclopropyl]pyrimidine-2,4-dione
• CAS: 171032-47-6
• 化学式: C₈H₁₀N₂O₃
• 分子量: 182.179
• InChiKey: UMIBAQGXMVUTBS-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'S,2'R)-1-<2-(Hydroxymethyl)cyclopropyl>uracil 在 吡啶 、 2-氯苯基二氯膦 作用下， 反应 74.0h， 生成 (1'S,2'R)-1-<2-(Acetoxymethyl)cyclopropyl>-4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides

  摘要：

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.

  DOI：

  10.1021/jo00121a047
• 作为产物：
  描述：

  1-[(1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropyl]pyrimidine-2,4-dione 在 盐酸 、 sodium tetrahydroborate 、 sodium periodate 作用下， 以 甲醇 为溶剂， 反应 16.34h， 生成 (1'S,2'R)-1-<2-(Hydroxymethyl)cyclopropyl>uracil
  参考文献：
  名称：

  Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides

  摘要：

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.

  DOI：

  10.1021/jo00121a047

文献信息

• Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides
  作者：Yufen Zhao、Tefang Yang、Migyoung Lee、Doowon Lee、M. Gary Newton、Chung K. Chu

  DOI：10.1021/jo00121a047

  日期：1995.8

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.