(+/-)-3-benzoyl-1-[(1 RS)-2,2-di(benzyloxymethyl)-3,3-difluorocyclopropylmethyl]-5-fluoro-1,2,3,4-tetrahydro-2,4-pyrimidinedione | 220825-86-5

• 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-[(1 RS)-2,2-di(benzyloxymethyl)-3,3-difluorocyclopropylmethyl]-5-fluoro-1,2,3,4-tetrahydro-2,4-pyrimidinedione
• 英文别名: 3-benzoyl-1-[[2,2-difluoro-3,3-bis(phenylmethoxymethyl)cyclopropyl]methyl]-5-fluoropyrimidine-2,4-dione
• CAS: 220825-86-5
• 化学式: C₃₁H₂₇F₃N₂O₅
• 分子量: 564.561
• InChiKey: UHOUYLSCPKHBCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  79.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+/-)-3-benzoyl-1-[(1 RS)-2,2-di(benzyloxymethyl)-3,3-difluorocyclopropylmethyl]-5-fluoro-1,2,3,4-tetrahydro-2,4-pyrimidinedione 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以92%的产率得到(+/-)-1-[(1 RS)-2,2-di(benzyloxymethyl)-3,3-difluorocyclopropylmethyl]-5-fluoro-1,2,3,4-tetrahydro-2,4-pyrimidinedione
  参考文献：
  名称：

  Preparation of novel difluorocyclopropane nucleosides

  摘要：

  Novel difluorinated cyclopropane nucleoside analogues possessing both two vicinal hydroxymethyl groups and a methylene spacer between the base and the ring were synthesized starting from 1,3-dibenzyloxy-2-propanol. After oxidation, olefination, reduction and acetylation the target molecules were obtained by difluoro; cyclopropanation, deacetylation and Mitsunobu reactions followed by two consecutive deprotection steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01067-9
• 作为产物：
  描述：

  4-(苄氧基)-3-<(苄氧基)甲基>-2-丁烯-1-醇 在 sodium methylate 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 二乙二醇二甲醚 为溶剂， 反应 17.5h， 生成 (+/-)-3-benzoyl-1-[(1 RS)-2,2-di(benzyloxymethyl)-3,3-difluorocyclopropylmethyl]-5-fluoro-1,2,3,4-tetrahydro-2,4-pyrimidinedione
  参考文献：
  名称：

  Preparation of novel difluorocyclopropane nucleosides

  摘要：

  Novel difluorinated cyclopropane nucleoside analogues possessing both two vicinal hydroxymethyl groups and a methylene spacer between the base and the ring were synthesized starting from 1,3-dibenzyloxy-2-propanol. After oxidation, olefination, reduction and acetylation the target molecules were obtained by difluoro; cyclopropanation, deacetylation and Mitsunobu reactions followed by two consecutive deprotection steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01067-9