3-Benzoyl-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrimidine-2,4-dione | 615286-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Benzoyl-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrimidine-2,4-dione
• 英文别名: 3-benzoyl-1-[[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]pyrimidine-2,4-dione
• CAS: 615286-30-1
• 化学式: C₁₉H₂₀N₂O₅
• 分子量: 356.378
• InChiKey: FOHHPMDAILLTSK-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Benzoyl-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrimidine-2,4-dione 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以100%的产率得到1-((4S,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  An unusual acetonide group migration

  摘要：

  Treatment of (2S,3R)-2,3-O-isopropyliden-4-penten-1,2,3-triol mesylate with uracil, K2CO3 did not provide the product of S(N)2 displacement, but an interesting acetonide group migration product 8. The structure of 8 was secured by spectral analysis and single crystal X-ray analysis. The desired product 2 could be ultimately obtained by Mitsunobu reaction of the alcohol 6 with 3-N-benzoyl uracil followed by basic hydrolysis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01758-1
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 potassium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 N,N'-羰基二咪唑 、 锌 、 碘甲烷 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 2.42h， 生成 3-Benzoyl-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  An unusual acetonide group migration

  摘要：

  Treatment of (2S,3R)-2,3-O-isopropyliden-4-penten-1,2,3-triol mesylate with uracil, K2CO3 did not provide the product of S(N)2 displacement, but an interesting acetonide group migration product 8. The structure of 8 was secured by spectral analysis and single crystal X-ray analysis. The desired product 2 could be ultimately obtained by Mitsunobu reaction of the alcohol 6 with 3-N-benzoyl uracil followed by basic hydrolysis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01758-1