(1S,23S,27S,49S)-12,38-dibenzyl-25,51-di-(tert-butyl)-25,51-dimethyl-3,6,9,15,18,21,24,26,29,32,35,41,44,47,50,52-hexadecaoxa-12,38-diazatricyclo[47.3.0.023,27]-dopentacontane | 671796-17-1

• 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: (1S,23S,27S,49S)-12,38-dibenzyl-25,51-di-(tert-butyl)-25,51-dimethyl-3,6,9,15,18,21,24,26,29,32,35,41,44,47,50,52-hexadecaoxa-12,38-diazatricyclo[47.3.0.023,27]-dopentacontane
• 英文别名: (1S,23S,27S,49S)-12,38-dibenzyl-25,51-di-(tert-butyl)-25,51-dimethyl-3,6,9,15,18,21,24,26,29,32,35,41,44,47,50,52-hexadecaoxa-12,38-diazatricyclo[47.3.0.0^23,27]-dopentacontane
• CAS: 671796-17-1
• 化学式: C₅₈H₉₈N₂O₁₆
• 分子量: 1079.42
• InChiKey: WLODKCZIDULMQY-OCCDUGCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  76.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  154.16
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (1S,23S,27S,49S)-12,38-dibenzyl-25,51-di-(tert-butyl)-25,51-dimethyl-3,6,9,15,18,21,24,26,29,32,35,41,44,47,50,52-hexadecaoxa-12,38-diazatricyclo[47.3.0.023,27]-dopentacontane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以93%的产率得到(1S,23S,27S,49S)-25,51-di-(tert-butyl)-25,51-dimethyl-3,6,9,15,18,21,24,26,29,32,35,41,44,47,50,52-hexadecaoxa-12,38-diazatricyclo[47.3.0.0^23,27]-dopentacontane
  参考文献：
  名称：

  Synthesis and Enantiodifferentiating Properties of Chiral Aza Crown Ethers

  摘要：

  Alkylation of 2-substituted (4S,5S)-4,5-bis(hydroxymethyl)-1,3-dioxolanes with 9-benzyl-1,17-di-iodo-3,6,12,15-tetraoxa-9-azaheptadecane afforded new chiral aza and diaza crown ethers as a result of [1+1] and [2+2] additions. Their catalytic debenzylation gave the corresponding derivatives with a secondary amino group. The reaction of diethyl (+)-tartrate and diethyl (4S,5S)-1,3-dioxolane-4,5-diacetates with 1,8-diamino-3,6-dioxaoctane led to formation of chiral macrocyclic lactams which were reduced with lithium aluminum hydride. The resulting diaza crown ethers were tested for enantioselectivity in complex formation with L- and D-valine methyl ester by the potentiometric method. In most cases, the aza crown ethers showed better enantioselectivity than their oxygen analogs.

  DOI：

  10.1023/b:rujo.0000003200.41968.46
• 作为产物：
  描述：

  N-苄基-2-[2-(2-氯乙氧基)乙氧基]-N-[2-[2-(2-氯乙氧基)乙氧基]乙基]乙胺 在 sodium hydride 、 sodium iodide 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 31.0h， 生成 (1S,23S,27S,49S)-12,38-dibenzyl-25,51-di-(tert-butyl)-25,51-dimethyl-3,6,9,15,18,21,24,26,29,32,35,41,44,47,50,52-hexadecaoxa-12,38-diazatricyclo[47.3.0.023,27]-dopentacontane
  参考文献：
  名称：

  Synthesis and Enantiodifferentiating Properties of Chiral Aza Crown Ethers

  摘要：

  Alkylation of 2-substituted (4S,5S)-4,5-bis(hydroxymethyl)-1,3-dioxolanes with 9-benzyl-1,17-di-iodo-3,6,12,15-tetraoxa-9-azaheptadecane afforded new chiral aza and diaza crown ethers as a result of [1+1] and [2+2] additions. Their catalytic debenzylation gave the corresponding derivatives with a secondary amino group. The reaction of diethyl (+)-tartrate and diethyl (4S,5S)-1,3-dioxolane-4,5-diacetates with 1,8-diamino-3,6-dioxaoctane led to formation of chiral macrocyclic lactams which were reduced with lithium aluminum hydride. The resulting diaza crown ethers were tested for enantioselectivity in complex formation with L- and D-valine methyl ester by the potentiometric method. In most cases, the aza crown ethers showed better enantioselectivity than their oxygen analogs.

  DOI：

  10.1023/b:rujo.0000003200.41968.46