1,3-bis<1-benzyl-5-methyl-4-((2-hydroxyimino)-1,3-dioxobutyl)-imidazol-2-yl>benzene | 137389-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-bis<1-benzyl-5-methyl-4-((2-hydroxyimino)-1,3-dioxobutyl)-imidazol-2-yl>benzene
• CAS: 137389-52-7
• 化学式: C₃₆H₃₂N₆O₆
• 分子量: 644.687
• InChiKey: DLXCPJMGRLPVOY-UHFFFAOYSA-N

物化性质

• 沸点：
  953.7±75.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  169.1
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,3-bis<1-benzyl-5-methyl-4-((2-hydroxyimino)-1,3-dioxobutyl)-imidazol-2-yl>benzene 在 lithium hydroxide 、 4 A molecular sieve 作用下， 以 环丁砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 生成 3,9,17,23-tetrabenzyl-4,8,18,22-tetramethyl-3,9,17,23,30,31,33,34-octazaheptacyclo[23.3.1.12,5.17,10.111,15.116,19.121,24]tetratriaconta-1(29),2(34),4,7,10(33),11(32),12,14,16(31),18,21,24(30),25,27-tetradecaene-6,20-dione
  参考文献：
  名称：

  Synthesis of mutidentate imidazole-containing macrocycles

  摘要：

  All three possible monomeric macrocyclic products and one dimeric product have now been isolated and spectrally characterized from the recently described3 macrocyclization reaction which leads to imidazole-containing coronands. Alkali metal ion promoted reactions provide a small selectivity for the largest of the three monomeric macrocycles, coronand 1, and leads to improved yields (5-7%). Regioselective internal vs external N-alkylation of the imidazole derivatives of 1 is controlled by the counter cation employed. Small cations lead to external N-alkylation, while large cations lead to internal N-alkylation. This is evidence of selective cation binding within the cavity for the lithium and sodium imidazolates, but for potassium and larger ions, binding is at the external peripheral nitrogen atoms. Larger ions are likely excluded from the cavity because of the higher conformational energy costs involved. The X-ray structure of the symmetrically protected derivative of 1 has been obtained and confirms previous structural assignments.

  DOI：

  10.1021/jo00030a038
• 作为产物：
  描述：

  生成 1,3-bis<1-benzyl-5-methyl-4-((2-hydroxyimino)-1,3-dioxobutyl)-imidazol-2-yl>benzene
  参考文献：
  名称：

  含大环四咪唑的合成：新的配体类别

  摘要：

  含新咪唑的大环化合物的第一个成员1（）已制备并进行了光谱表征。利用苄胺与2-氧亚氨基-1,3-二羰基化合物的母体反应，与咪唑环结构同时实现大环化。

  DOI：

  10.1016/s0040-4039(00)92699-6