(2S,3R,8R,12R,17R,18S)-2,18-diethyl-1-methyl-3,8,12,17-tetraphenyl-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane | 150126-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2S,3R,8R,12R,17R,18S)-2,18-diethyl-1-methyl-3,8,12,17-tetraphenyl-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane
• 英文别名: (5R,6S,8S,9R,14R,18R)-6,8-diethyl-7-methyl-5,9,14,18-tetraphenyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 150126-01-5
• 化学式: C₄₁H₅₂N₂O₄
• 分子量: 636.875
• InChiKey: IDBRUBXJVLLRRE-PRFXMNKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.11
• 重原子数：
  47.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.19
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (2S,3R,8R,12R,17R,18S)-2,18-diethyl-1-methyl-3,8,12,17-tetraphenyl-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane 在 甲酸 作用下， 以 水 为溶剂， 生成 (2S,3R,8R,12R,17R,18S)-2,18-diethyl-1,10-dimethyl-3,8,12,17-tetraphenyl-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane
  参考文献：
  名称：

  Synthesis of chiral diaza-18-crown-6 derivatives from optically active diethanolamines

  摘要：

  Homotopic 1,10-diaza-18-crown-6 derivatives with two, four, and six chiral centers have been prepared in optically active form from diethanolamines via a cyclization reaction with tosylates 39 and 48. The requisite optically active diethanolamines were prepared from chiral cyanohydrins and chiral ethanolamines by a one-pot Grignard-transimination-reduction or a one-pot reduction-transimination-reduction procedure. Yields were strongly affected by the size of the substituents alpha to the nitrogen atom. The stereoselectivity of the diethanolamine synthesis was found to depend on the configuration of the ethanolamine used.

  DOI：

  10.1021/jo00068a029
• 作为产物：
  描述：

  (2S,3R,8R,12R,17R,18S)-2,18-diethyl-1-methyl-3,8,12,17-tetraphenyl-10-(p-tolylsulfonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到(2S,3R,8R,12R,17R,18S)-2,18-diethyl-1-methyl-3,8,12,17-tetraphenyl-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane
  参考文献：
  名称：

  Synthesis of chiral diaza-18-crown-6 derivatives from optically active diethanolamines

  摘要：

  Homotopic 1,10-diaza-18-crown-6 derivatives with two, four, and six chiral centers have been prepared in optically active form from diethanolamines via a cyclization reaction with tosylates 39 and 48. The requisite optically active diethanolamines were prepared from chiral cyanohydrins and chiral ethanolamines by a one-pot Grignard-transimination-reduction or a one-pot reduction-transimination-reduction procedure. Yields were strongly affected by the size of the substituents alpha to the nitrogen atom. The stereoselectivity of the diethanolamine synthesis was found to depend on the configuration of the ethanolamine used.

  DOI：

  10.1021/jo00068a029