N-[5-[3-((S)-1-cyclopropyl-but-3-enyloxy)-4,5-dimethoxy-benzyl]-4-(2,2-dimethyl-propionylamino)-pyrimidin-2-yl]-2,2-dimethyl-propionamide | 1228103-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[5-[3-((S)-1-cyclopropyl-but-3-enyloxy)-4,5-dimethoxy-benzyl]-4-(2,2-dimethyl-propionylamino)-pyrimidin-2-yl]-2,2-dimethyl-propionamide
• 英文别名: N-[5-[[3-[(1S)-1-cyclopropylbut-3-enoxy]-4,5-dimethoxyphenyl]methyl]-2-(2,2-dimethylpropanoylamino)pyrimidin-4-yl]-2,2-dimethylpropanamide
• CAS: 1228103-69-2
• 化学式: C₃₀H₄₂N₄O₅
• 分子量: 538.687
• InChiKey: QVUSWLGRPKDFGN-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[5-[3-((S)-1-cyclopropyl-but-3-enyloxy)-4,5-dimethoxy-benzyl]-4-(2,2-dimethyl-propionylamino)-pyrimidin-2-yl]-2,2-dimethyl-propionamide 在 potassium osmate(VI) dihydrate 、 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 N-[5-[[3-[(1S)-1-cyclopropyl-3-oxopropoxy]-4,5-dimethoxyphenyl]methyl]-2-(2,2-dimethylpropanoylamino)pyrimidin-4-yl]-2,2-dimethylpropanamide
  参考文献：
  名称：

  Enantioselective Synthesis of Iclaprim Enantiomers―A Versatile Approach to 2-Substituted Chiral Chromenes

  摘要：

  Both enantiomers of the DHFR inhibitor iclaprim (R)-1 and (5)-1 were synthesized from the cyclopropyl homoallyl alcohols (R)-6 and (S)-6. respectively. As key steps these transformations include a Mitsunobu reaction and the formation of the diaminopyrimidine unit prior to a novel cyclization procedure to obtain the desired chromene heterocycle. The moderate enantioselectivity of the products (R)-1 and OH is related to the Mitsunobu reaction, which unfortunately did not proceed with complete inversion or configuration.

  DOI：

  10.1021/jo100566c
• 作为产物：
  描述：

  5-[[3-[(1S)-1-cyclopropylbut-3-enoxy]-4,5-dimethoxyphenyl]methyl]pyrimidine-2,4-diamine 、 三甲基乙酸酐 反应 1.0h， 生成 N-[5-[3-((S)-1-cyclopropyl-but-3-enyloxy)-4,5-dimethoxy-benzyl]-4-(2,2-dimethyl-propionylamino)-pyrimidin-2-yl]-2,2-dimethyl-propionamide
  参考文献：
  名称：

  Enantioselective Synthesis of Iclaprim Enantiomers―A Versatile Approach to 2-Substituted Chiral Chromenes

  摘要：

  Both enantiomers of the DHFR inhibitor iclaprim (R)-1 and (5)-1 were synthesized from the cyclopropyl homoallyl alcohols (R)-6 and (S)-6. respectively. As key steps these transformations include a Mitsunobu reaction and the formation of the diaminopyrimidine unit prior to a novel cyclization procedure to obtain the desired chromene heterocycle. The moderate enantioselectivity of the products (R)-1 and OH is related to the Mitsunobu reaction, which unfortunately did not proceed with complete inversion or configuration.

  DOI：

  10.1021/jo100566c