(8R,9S)-8,9-Di-furan-2-yl-1,4-dioxa-7,10-diaza-cyclododecane | 143062-21-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (8R,9S)-8,9-Di-furan-2-yl-1,4-dioxa-7,10-diaza-cyclododecane
• CAS: 143062-21-9
• 化学式: C₁₆H₂₂N₂O₄
• 分子量: 306.362
• InChiKey: WCHVJXRKRWQSDQ-IYBDPMFKSA-N

物化性质

• 沸点：
  448.6±40.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

反应信息

• 作为产物：
  描述：

  [1-Furan-2-yl-meth-(E)-ylidene]-{2-[2-(2-{[1-furan-2-yl-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 (8R,9S)-8,9-Di-furan-2-yl-1,4-dioxa-7,10-diaza-cyclododecane 、 (8S,9S)-8,9-Di-furan-2-yl-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+.