(2S,3R,17R,18S)-2,18-diethyl-3,17-diphenyl-1-methyl-10-(p-tolylsulfonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane | 150125-86-3

• 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: (2S,3R,17R,18S)-2,18-diethyl-3,17-diphenyl-1-methyl-10-(p-tolylsulfonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane
• 英文别名: (5R,6S,8S,9R)-6,8-diethyl-7-methyl-16-(4-methylphenyl)sulfonyl-5,9-diphenyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 150125-86-3
• 化学式: C₃₆H₅₀N₂O₆S
• 分子量: 638.869
• InChiKey: XYDHANUGVFMXOD-CLLHQPRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  45.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.54
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,17R,18S)-2,18-diethyl-3,17-diphenyl-1-methyl-10-(p-tolylsulfonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane 在 lithium aluminium tetrahydride 、 甲酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2S,3R,17R,18S)-2,18-diethyl-1,10-dimethyl-3,17-diphenyl-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：

  N,N-bis<2-(2-hydroxyethoxy)ethyl>-p-toluenesulfonamide 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2S,3R,17R,18S)-2,18-diethyl-3,17-diphenyl-1-methyl-10-(p-tolylsulfonyl)-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