25,27-dihydroxycalix<4>arene | 145237-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 25,27-dihydroxycalix<4>arene
• 英文别名: 25,27-dihydroxycalix[4]arene；25,27-Dihydroxy calix[4]arene；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-25,27-diol
• CAS: 145237-29-2
• 化学式: C₂₈H₂₄O₂
• 分子量: 392.497
• InChiKey: QTIVWFXLYWGHQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氟苯腈 、 25,27-dihydroxycalix<4>arene 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 60.0h， 以252 mg的产率得到
  参考文献：
  名称：

  摘要：

  Three 25,27-dihydrocalix[4]arene derivatives, bearing benzonitrile and acetone groups on the oxygens, were prepared and structurally characterized. All three structures crystallize in P(1) over bar, with cell dimensions: bis(benzonitrile)calix[4]arene.toluene, a = 11.530(2) Angstrom, b = 12.013(2) Angstrom, c = 14.089(4) Angstrom, alpha = 103.555(18)degrees, beta = 94.341(18)degrees, gamma = 104.704(16)degrees, and V = 1815.9(7) Angstrom(3); anti-bis-acetone-calix[4]arene, a = 7.5847(8) Angstrom, b = 12.0948(17) Angstrom, c = 15.3375(16) Angstrom, alpha = 78.982(10)degrees, beta = 76.932(9)degrees, gamma = 73.129(10)degrees, and V = 1299.6(3) Angstrom(3); syn-bis-acetone-calix[4]arene, a = 9.080(3) Angstrom, b = 10.391(3) Angstrom, c = 14.816(3) Angstrom, alpha = 96.998(19)degrees, beta = 100.02(2)degrees, gamma = 103.93(3)degrees, and V = 1299.6(3) Angstrom(3).

  DOI：

  10.1023/a:1015692205903
• 作为产物：
  描述：

  O,O-双(二乙氧基磷酰基)杯[4]芳香烃 在 氨 、 氢化钾 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到25,27-dihydroxycalix<4>arene
  参考文献：
  名称：

  Transduction of selective recognition of heavy metal ions by chemically modified field effect transistors (CHEMFETs)

  摘要：

  Specifically substituted calix[4]arenes that complex selectively silver (2), copper (13), cadmium (23), and lead (29) cations were synthesized via di- and tetraalkylation of p-tert-butylcalix[4]arene. Calix[4]arenes derivatized with thioether, thioamide, and dithiocarbamoyl functionalities could be obtained in high overall yields. Integrated on a chemically modified field effect transistor (CHEMFET) the selective complexation of heavy metal ions by these calix[4]arenes is transduced directly into an electrical signal. An architecture for CHEMFETs is used in which a hydrophilic polyHEMA hydrogel is covalently attached between the gate oxide surface of a modified ISFET and the hydrophobic sensing membrane that contains the receptor molecule. CHEMFETs based on the calix[4]arene (2) with two diametrically substituted thioether functionalities responded selectively (60 mV decade-1) to a change in silver activity in the aqueous solution in the presence of potassium, calcium, cadmium, and copper ions (log K(ij) less-than-or-equal-to -4). The selectivity toward mercury (log K(ij) = -2.7) is comparable to the best neutral carrier based ISE so far. The calix[4]arene (13), with four dithiocarbamoyl groups, incorporated in a CHEMFET responsed Nernstian (30 mV decade-1) to a change in copper activity. The calix[4]arene (23), which has four dimethylthiocarbamoylmethoxyethoxy substituents, was selective in a CHEMFET (30 mV decade-1) toward cadmium in the presence of calcium and potassium ions. Two classes of ionophores can be distinguished for the selective detection of lead(II) cations by CHEMFETs, oxamide and thioamide ionophores, respectively. Tetrasubstitution of the calix[4]arene with thioamide groups (29) is a prerequisite for the selective detection of lead and leads to a highly selective CHEMFET (log K(ij) -3.4 to -5.2).

  DOI：

  10.1021/ja00052a063

文献信息

• Dideoxygenated calix[4]arene crown-6 ethers enhanced selectivity for caesium over potassium and rubidium
  作者：Richard A. Sachleben、Agathe Urvoas、Jeffrey C. Bryan、Tamara J. Haverlock、Bruce A. Moyer、Benjamin P. Hay

  DOI：10.1039/a905682c

  日期：——

  Calix[4]arene crown-6 ethers derived from dideoxygenated calix[4]arene exhibit enhanced extraction selectivity for caesium over potassium; the crystal stucture of the uncomplexed calix[4]arene monobenzocrown-6 ether exists in the 1,3-alt conformation in the solid state.

  源自双脱氧杯[4]芳烃的杯[4]芳烃冠6醚对铯的萃取选择性高于对钾的萃取选择性；未络合的杯[4]芳烃单苯并冠6醚的晶体结构在固态时以1,3-alt构象存在。
• A new highly selective calix[4]crown-6 fluorescent caesium probe
  作者：Hai-Feng Ji、Reza Dabestani、Gilbert M. Brown、Richard A. Sachleben

  DOI：10.1039/a908720f

  日期：——

  We have synthesized 1,3-alternate di-deoxygenated calix[4](9-cyano-10-anthrylmethyl)benzocrown-6, 1 and 1,3-alternate calix[4](9-cyano-10-anthrylmethyl)benzocrown-6, 2 as the second generation of caesium selective fluorescent probes; probe 1 shows 54-fold fluorescence enhancement upon caesium complexation while 2 exhibits only 8-fold enhancement; the selectivity ratios for 1 to complex caesium ion over potassium and rubidium (KCs/KK and KCs/KRb) are ca. 10 fold higher than those of 2 for the same ions; the observed selectivity ratios are consistent with data reported for other 1,3-alternate calix[4]crown-6 derivatives.

  我们合成了1,3-交替二脱氧的杯[4](9-氰基-10-蒽基甲基)苯并冠-6、1和1,3-交替杯[4](9-氰基-10-蒽基甲基)苯并冠-6、2，作为第二代铯选择性荧光探针；探针1在铯络合时显示出54倍的荧光增强，而探针2仅显示出8倍的荧光增强；探针1与铯离子络合的选择性比率（KCs/KK和KCs/KRb）比探针2与相同离子络合的选择性比率（KCs/KK和KCs/KRb）高出约10倍；观察到的选择性比率与其它1,3-交替杯[4]冠-6衍生物的数据一致。
• Transduction of selective recognition of heavy metal ions by chemically modified field effect transistors (CHEMFETs)
  作者：Peter L. H. M. Cobben、Richard J. M. Egberink、Johan G. Bomer、Piet Bergveld、Willem Verboom、David N. Reinhoudt

  DOI：10.1021/ja00052a063

  日期：1992.12

  Specifically substituted calix[4]arenes that complex selectively silver (2), copper (13), cadmium (23), and lead (29) cations were synthesized via di- and tetraalkylation of p-tert-butylcalix[4]arene. Calix[4]arenes derivatized with thioether, thioamide, and dithiocarbamoyl functionalities could be obtained in high overall yields. Integrated on a chemically modified field effect transistor (CHEMFET) the selective complexation of heavy metal ions by these calix[4]arenes is transduced directly into an electrical signal. An architecture for CHEMFETs is used in which a hydrophilic polyHEMA hydrogel is covalently attached between the gate oxide surface of a modified ISFET and the hydrophobic sensing membrane that contains the receptor molecule. CHEMFETs based on the calix[4]arene (2) with two diametrically substituted thioether functionalities responded selectively (60 mV decade-1) to a change in silver activity in the aqueous solution in the presence of potassium, calcium, cadmium, and copper ions (log K(ij) less-than-or-equal-to -4). The selectivity toward mercury (log K(ij) = -2.7) is comparable to the best neutral carrier based ISE so far. The calix[4]arene (13), with four dithiocarbamoyl groups, incorporated in a CHEMFET responsed Nernstian (30 mV decade-1) to a change in copper activity. The calix[4]arene (23), which has four dimethylthiocarbamoylmethoxyethoxy substituents, was selective in a CHEMFET (30 mV decade-1) toward cadmium in the presence of calcium and potassium ions. Two classes of ionophores can be distinguished for the selective detection of lead(II) cations by CHEMFETs, oxamide and thioamide ionophores, respectively. Tetrasubstitution of the calix[4]arene with thioamide groups (29) is a prerequisite for the selective detection of lead and leads to a highly selective CHEMFET (log K(ij) -3.4 to -5.2).
• ——
  作者：Jeffrey C. Bryan、Nancy L. Engle、Richard A. Sachleben

  DOI：10.1023/a:1015692205903

  日期：——

  Three 25,27-dihydrocalix[4]arene derivatives, bearing benzonitrile and acetone groups on the oxygens, were prepared and structurally characterized. All three structures crystallize in P(1) over bar, with cell dimensions: bis(benzonitrile)calix[4]arene.toluene, a = 11.530(2) Angstrom, b = 12.013(2) Angstrom, c = 14.089(4) Angstrom, alpha = 103.555(18)degrees, beta = 94.341(18)degrees, gamma = 104.704(16)degrees, and V = 1815.9(7) Angstrom(3); anti-bis-acetone-calix[4]arene, a = 7.5847(8) Angstrom, b = 12.0948(17) Angstrom, c = 15.3375(16) Angstrom, alpha = 78.982(10)degrees, beta = 76.932(9)degrees, gamma = 73.129(10)degrees, and V = 1299.6(3) Angstrom(3); syn-bis-acetone-calix[4]arene, a = 9.080(3) Angstrom, b = 10.391(3) Angstrom, c = 14.816(3) Angstrom, alpha = 96.998(19)degrees, beta = 100.02(2)degrees, gamma = 103.93(3)degrees, and V = 1299.6(3) Angstrom(3).