(8S,9R)-8,9-Bis-(4-methoxy-phenyl)-1,4-dioxa-7,10-diaza-cyclododecane | 143062-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (8S,9R)-8,9-Bis-(4-methoxy-phenyl)-1,4-dioxa-7,10-diaza-cyclododecane
• 英文别名: (8S,9R)-8,9-bis(4-methoxyphenyl)-1,4-dioxa-7,10-diazacyclododecane
• CAS: 143062-18-4
• 化学式: C₂₂H₃₀N₂O₄
• 分子量: 386.491
• InChiKey: WNLLWEDOUGJKKV-SZPZYZBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-{2-[2-(2-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-ethoxy)-ethoxy]-ethyl}-amine 在 甲烷磺酸 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (8S,9R)-8,9-Bis-(4-methoxy-phenyl)-1,4-dioxa-7,10-diaza-cyclododecane 、 (8R,9R)-8,9-Bis-(4-methoxy-phenyl)-1,4-dioxa-7,10-diaza-cyclododecane
  参考文献：
  名称：

  Synthesis of Nitrogen-Containing Macrocycles with Reductive Intramolecular Coupling of Aromatic Diimines

  摘要：

  Reductive intramolecular coupling of aromatic diimines is an effective method for the synthesis of a variety of nitrogen-containing macrocycles. 1,4-Diazacrown ethers 3 were effectively synthesized by intramolecular coupling of bis(imino ethers) 9 promoted by electroreduction (method A) or chemical reduction with zinc powder (method B) in the presence of methanesulfonic acid. In spite of the formation of macrocycles, the yields of 3 were relatively high. This can be explained by the formation of proton-bridged intermediates 14, in which intramolecular hydrogen bonds are formed between hydrogen and oxygen atoms of diiminium salts. Method B was more effective in the formation of 1,4-diaza-12-crown-4 derivatives 3 (n = 1) due to the template effect of Zn2+. Optically active macrocyclic bislactones 4 were synthesized stereoselectively by reductive intramolecular coupling of bis(imino esters) 20 with zinc powder (method B). The high stereoselectivity is explained by considering proton-bridged intermediate 23. The resultant compounds 4 were transformed to optically active 1,2-diarylethylenediamines 7. Various sizes of macrocyclic bislactams 5 were synthesized by reductive intramolecular coupling of bis(imino amides) 26 with zinc powder (method B). Reduction of 5 gave the corresponding macrocyclic polyamines 6.

  DOI：

  10.1021/jo00118a013

文献信息

• Novel synthesis of 1,4-diazacrown ethers by reductive coupling of aromatic diimines
  作者：Tatsuya Shono、Naoki Kise、Eiichi Okazaki

  DOI：10.1016/s0040-4039(00)92085-9

  日期：1992.6

  The electroreduction or chemical reduction with zinc powder has been found to be effective to intramolecular coupling of aromatic diimines yielding 1,4-diazacrown ethers. The latter reduction was particularly effective to formation of 1,4-diaza-12-crown-4 derivatives due to the template effect of Zn2+.