25,27-dihydroxy-26,28-bis(methoxyethoxy)calix<4>arene-11,23-dicarboxaldehyde | 143406-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,27-dihydroxy-26,28-bis(methoxyethoxy)calix<4>arene-11,23-dicarboxaldehyde
• 英文别名: 26,28-Dihydroxy-25,27-bis(2-methoxyethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-5,17-dicarbaldehyde
• CAS: 143406-36-4
• 化学式: C₃₆H₃₆O₈
• 分子量: 596.677
• InChiKey: PCAMXABURZHBBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸2-甲氧基乙酯 、 25,27-dihydroxy-26,28-bis(methoxyethoxy)calix<4>arene-11,23-dicarboxaldehyde 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 25,26,27,28-Tetrakis(2-methoxyethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-5,17-dicarbaldehyde
  参考文献：
  名称：

  Tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation

  摘要：

  A general method has been developed for the preparation f tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation (3a,c-e) starting from p-tert-butylcalix[4]arenes 1a,b using Cs2CO3 in DMF. The 1,3-alternate conformation was unequivocally proved by an X-ray structure determination of 3a. The scope of the reaction was investigated starting from a series of diametrically di-O-alkylated calix[4]arenes 4a-e having different substituents R2 (t-Bu, CHO, NO2, Br, CN) at the para positions of the phenolic rings. The reactions of 4a-d (R2 = t-Bu, CHO, NO2, Br) yielded the corresponding tetra-0-alkylated calix[4]arenes in the 1,3-alternate conformation 5a-d (51-73%). However, the dicyanocalix[4]arene 4e gave the partial cone conformer 6 as the major reaction product.

  DOI：

  10.1021/jo00046a021
• 作为产物：
  描述：

  杯[4]芳烃 在 四氯化钛 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.33h， 生成 25,27-dihydroxy-26,28-bis(methoxyethoxy)calix<4>arene-11,23-dicarboxaldehyde
  参考文献：
  名称：

  Tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation

  摘要：

  A general method has been developed for the preparation f tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation (3a,c-e) starting from p-tert-butylcalix[4]arenes 1a,b using Cs2CO3 in DMF. The 1,3-alternate conformation was unequivocally proved by an X-ray structure determination of 3a. The scope of the reaction was investigated starting from a series of diametrically di-O-alkylated calix[4]arenes 4a-e having different substituents R2 (t-Bu, CHO, NO2, Br, CN) at the para positions of the phenolic rings. The reactions of 4a-d (R2 = t-Bu, CHO, NO2, Br) yielded the corresponding tetra-0-alkylated calix[4]arenes in the 1,3-alternate conformation 5a-d (51-73%). However, the dicyanocalix[4]arene 4e gave the partial cone conformer 6 as the major reaction product.

  DOI：

  10.1021/jo00046a021

文献信息

• Tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation
  作者：Willem Verboom、Sumana Datta、Zouhair Asfari、Sybolt Harkema、David N. Reinhoudt

  DOI：10.1021/jo00046a021

  日期：1992.9

  A general method has been developed for the preparation f tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation (3a,c-e) starting from p-tert-butylcalix[4]arenes 1a,b using Cs2CO3 in DMF. The 1,3-alternate conformation was unequivocally proved by an X-ray structure determination of 3a. The scope of the reaction was investigated starting from a series of diametrically di-O-alkylated calix[4]arenes 4a-e having different substituents R2 (t-Bu, CHO, NO2, Br, CN) at the para positions of the phenolic rings. The reactions of 4a-d (R2 = t-Bu, CHO, NO2, Br) yielded the corresponding tetra-0-alkylated calix[4]arenes in the 1,3-alternate conformation 5a-d (51-73%). However, the dicyanocalix[4]arene 4e gave the partial cone conformer 6 as the major reaction product.