25-benzyloxy-27-methoxy-26,28-dihydroxycalix<4>arene | 223689-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25-benzyloxy-27-methoxy-26,28-dihydroxycalix<4>arene
• 英文别名: 25,27-dihydroxy-26-methoxy-28-phenylmethoxycalix[4]arene；26-Methoxy-28-phenylmethoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene-25,27-diol
• CAS: 223689-61-0
• 化学式: C₃₆H₃₂O₄
• 分子量: 528.648
• InChiKey: JVXRDPZAGIUSQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  25-benzyloxy-27-methoxy-26,28-dihydroxycalix<4>arene 在 5percent Pd/C 盐酸 、 氢气 、 sodium hydride 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 25,27-bis(dimethylaminocarbonylmethoxy)-26-hydroxy-28-methoxy-11-p-nitrophenyldiazacalix[4]arene
  参考文献：
  名称：

  Highly Selective Optical-Sensing Membranes, Containing Calix[4]arene Chromoionophores, for Pb2+ Ions

  摘要：

  Plasticized poly(vinyl chloride) (PVC) optode membranes containing novel calix[4]arene chromoionophores 1 or 2 and one equivalent of a lipophilic anion respond to Pb2+ ions with high selectivity over alkali, alkaline-earth, and other heavy metal ions. This selectivity stems from the combination of ligand specificity and a unique ion exchange scheme that employs both monovalent metal ions and protons as the exchanged ions. Complexation of Pb2+ ions inside the membrane is accompanied by deprotonation of the chromoionophores, which causes a bathochromic shift of the absorption maximum lambda(max). The response to Pb2+ ions is modulated by pH and alkali metal ions in a fashion that is consistent with the proposed ion-exchange mechanism. Of all of the other metal ions tested, only Cs+ and Ag+ produce a color change. However, these monovalent metal ions cause hypsochromic shifts of lambda(max) instead of the bathochromic shift caused by Pb2+, because the chromoionophores remain protonated upon complexation.

  DOI：

  10.1002/1521-3765(20011119)7:22<4878::aid-chem4878>3.0.co;2-8
• 作为产物：
  描述：

  25-benzyloxy-26,27,28-trihydroxycalix<4>arene 、 碘甲烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以88%的产率得到25-benzyloxy-27-methoxy-26,28-dihydroxycalix<4>arene
  参考文献：
  名称：

  用四种不同的“下缘”取代基合成杯[4]芳烃。

  摘要：

  按照六步序列合成具有四个不同“下边缘”取代基的杯[4]芳烃。使用R（1）X和CH（3）ONa引入第一个烷基（R（1）），然后与R（2）X和K（2）CO（3）反应导致引入第二个3位的烷基（R（2））。苯甲酸酯在1,3-O-二取代阶段被引入作为保护基，并在第三个烷基（R（3））与R（3）X和NaH结合后在碱性条件下被除去。将最终的烷基（R（4））与R（4）X和NaH引入，得到手性标题化合物。

  DOI：

  10.1021/jo981648l

文献信息

• Synthesis of Calix[4]arenes with Four Different “Lower Rim” Substituents
  作者：Chun-Mei Shu、Wen-Sheng Chung、Sing-Ho Wu、Zong-Chia Ho、Lee-Gin Lin

  DOI：10.1021/jo981648l

  日期：1999.4.1

  Calix[4]arenes with four different "lower rim" substituents were synthesized following six-step sequences. The first alkyl group (R(1)) was introduced using R(1)X and CH(3)ONa, and then reaction with R(2)X and K(2)CO(3) led to the introduction of a second alkyl group (R(2)) at the 3-position. Benzoate was introduced as a protecting group at the 1,3-O-disubstituent stage and was removed under basic

  按照六步序列合成具有四个不同“下边缘”取代基的杯[4]芳烃。使用R（1）X和CH（3）ONa引入第一个烷基（R（1）），然后与R（2）X和K（2）CO（3）反应导致引入第二个3位的烷基（R（2））。苯甲酸酯在1,3-O-二取代阶段被引入作为保护基，并在第三个烷基（R（3））与R（3）X和NaH结合后在碱性条件下被除去。将最终的烷基（R（4））与R（4）X和NaH引入，得到手性标题化合物。
• Highly Selective Optical-Sensing Membranes, Containing Calix[4]arene Chromoionophores, for Pb2+ Ions
  作者：Niels J. van der Veen、Ewa Rozniecka、Léon A. Woldering、Michal Chudy、Jurriaan Huskens、Frank C. J. M. van Veggel、David N. Reinhoudt

  DOI：10.1002/1521-3765(20011119)7:22<4878::aid-chem4878>3.0.co;2-8

  日期：2001.11.19

  Plasticized poly(vinyl chloride) (PVC) optode membranes containing novel calix[4]arene chromoionophores 1 or 2 and one equivalent of a lipophilic anion respond to Pb2+ ions with high selectivity over alkali, alkaline-earth, and other heavy metal ions. This selectivity stems from the combination of ligand specificity and a unique ion exchange scheme that employs both monovalent metal ions and protons as the exchanged ions. Complexation of Pb2+ ions inside the membrane is accompanied by deprotonation of the chromoionophores, which causes a bathochromic shift of the absorption maximum lambda(max). The response to Pb2+ ions is modulated by pH and alkali metal ions in a fashion that is consistent with the proposed ion-exchange mechanism. Of all of the other metal ions tested, only Cs+ and Ag+ produce a color change. However, these monovalent metal ions cause hypsochromic shifts of lambda(max) instead of the bathochromic shift caused by Pb2+, because the chromoionophores remain protonated upon complexation.