25,27-bis(ethoxyethoxy)-26,28-bis[(chloroethoxy)ethoxy]calix[4]arene | 190390-28-4

• 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-bis(ethoxyethoxy)-26,28-bis[(chloroethoxy)ethoxy]calix[4]arene
• 英文别名: 25,27-Bis[2-(2-chloroethoxy)ethoxy]-26,28-bis(2-ethoxyethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene
• CAS: 190390-28-4
• 化学式: C₄₄H₅₄Cl₂O₈
• 分子量: 781.814
• InChiKey: MGZPBRSHBAHATN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  54
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  25,27-bis(ethoxyethoxy)-26,28-bis[(chloroethoxy)ethoxy]calix[4]arene 、 25,27-bis(ethoxyethoxy)-26,28-bis(hydroxyethoxyethoxy)calix[4]arene 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以4%的产率得到72,73,81,82-tetrakis(2-ethoxyethoxy)-3,6,9,12,15,35,38,41,44,47-decaoxaundecacyclo[47.15.7.717,33.123,27.155,59.166,70.02,61.016,21.029,34.048,53.175,79]dooctaconta-1(64),2(61),16(21),17,19,23(81),24,26,29(34),30,32,48(53),49,51,55,57,59(73),62,66(72),67,69,75,77,79(82)-tetracosaene
  参考文献：
  名称：

  Ikedai; Kawaguchi; Shinkai, Anales de Quimica, 1997, vol. 93, # 6, p. 408 - 414

  摘要：

  DOI：
• 作为产物：
  描述：

  杯[4]芳烃 在 barium dihydroxide 、 caesium carbonate 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 25,27-bis(ethoxyethoxy)-26,28-bis[(chloroethoxy)ethoxy]calix[4]arene
  参考文献：
  名称：

  Molecular Design of a “Molecular Syringe” Mimic for Metal Cations Using a 1,3-Alternate Calix[4]arene Cavity

  摘要：

  A 1,3-alternate calix[4]arene bearing a nitrogen-containing crown cap at one side and a bis(ethoxyethoxy) group at another side has been synthesized. H-1 NMR spectroscopic studies showed that Ag+ is bound to the crown-capped side (log K-ass. = 9.78: CD2Cl2:CD3OD = 4:1 v/v,30 degrees C), and the dissociation of Ag+ from this cavity is very slow. When the nitrogen atom in the crown ring is protonated with trifluoroacetic acid, Ag+ is pushed out to the bis(ethoxyethoxy) side through a pi-basic tube of the 1,3-alternate calix[4]arene. The dissociation of the complex from the bis(ethoxyethoxy) side occurs relatively fast. On the other hand, when the nitrogen . H+ in the crown ring is deprotonated with Li2CO3 and diazabicycloundecene, Ag+ is sucked back to the crown-capped side through the pi-basic tube. These chemically-switchable actions well imitate the function of a ''syringe'', using the pi-basic tube as a pipette and the crown ring as a rubber cap. We believe that this prototype of a ''molecular syringe'' is a novel molecular architecture for the action of metal cations.

  DOI：

  10.1021/jo962040k

文献信息

• Ikedai; Kawaguchi; Shinkai, Anales de Quimica, 1997, vol. 93, # 6, p. 408 - 414
  作者：Ikedai、Kawaguchi、Shinkai

  DOI：——

  日期：——
• Molecular Design of a “Molecular Syringe” Mimic for Metal Cations Using a 1,3-Alternate Calix[4]arene Cavity
  作者：Atsushi Ikeda、Takanobu Tsudera、Seiji Shinkai

  DOI：10.1021/jo962040k

  日期：1997.5.1

  A 1,3-alternate calix[4]arene bearing a nitrogen-containing crown cap at one side and a bis(ethoxyethoxy) group at another side has been synthesized. H-1 NMR spectroscopic studies showed that Ag+ is bound to the crown-capped side (log K-ass. = 9.78: CD2Cl2:CD3OD = 4:1 v/v,30 degrees C), and the dissociation of Ag+ from this cavity is very slow. When the nitrogen atom in the crown ring is protonated with trifluoroacetic acid, Ag+ is pushed out to the bis(ethoxyethoxy) side through a pi-basic tube of the 1,3-alternate calix[4]arene. The dissociation of the complex from the bis(ethoxyethoxy) side occurs relatively fast. On the other hand, when the nitrogen . H+ in the crown ring is deprotonated with Li2CO3 and diazabicycloundecene, Ag+ is sucked back to the crown-capped side through the pi-basic tube. These chemically-switchable actions well imitate the function of a ''syringe'', using the pi-basic tube as a pipette and the crown ring as a rubber cap. We believe that this prototype of a ''molecular syringe'' is a novel molecular architecture for the action of metal cations.