5,11,17,23-tetra-(tert-butyl)-25-(3-hydroxypropoxy)-26,27,28-tris-hydroxycalix[4]arene | 1254972-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetra-(tert-butyl)-25-(3-hydroxypropoxy)-26,27,28-tris-hydroxycalix[4]arene
• 英文别名: 5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-hydroxypropyloxy)calix[4]arene；5,11,17,23-Tetratert-butyl-28-(3-hydroxypropoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27-triol
• CAS: 1254972-84-3
• 化学式: C₄₇H₆₂O₅
• 分子量: 707.006
• InChiKey: CKAPVJJKDDUBOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  52
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-(tert-butyl)-25-(3-hydroxypropoxy)-26,27,28-tris-hydroxycalix[4]arene 、 N,N'-羰基二咪唑 以 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  New potential prodrugs of aciclovir using calix[4]arene as a lipophilic carrier: synthesis and drug-release studies at the air–water interface

  摘要：

  两种四对叔丁基杯[4]芳烃物种通过碳酯键在下缘连接着一个或两个抗HSV阿昔洛韦单元，被合成为可能的抗病毒前药。使用Langmuir平衡在空气-水和空气-碳酸盐缓冲界面研究了这些衍生物的两亲性；形成的单层在两个亚相上都是稳定的。然后在pH 10和37°C的碳酸盐缓冲亚相上用这些分子形成的单层来监测二酯键的水解。通过HPLC观察到两种衍生物在3天内释放出约30%的游离阿昔洛韦。

  DOI：

  10.1039/c2nj40338b
• 作为产物：
  描述：

  5,11,17,23-tetra(tert-butyl)-25,27-bis-(3-hydroxypropoxy)-26,28-bis-hydroxycalix[4]arene 在 titanium(IV) chloride tetrahydrofuran 、 盐酸 、 水 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以70%的产率得到5,11,17,23-tetra-(tert-butyl)-25-(3-hydroxypropoxy)-26,27,28-tris-hydroxycalix[4]arene
  参考文献：
  名称：

  Easy and Selective Method for the Synthesis of Various Mono-O-functionalized Calix[4]arenes: De-O-functionalization Using TiCl₄

  摘要：

  An efficient and selective method for the monofunctionalization of p-tert-butylcalix[4]arene is described A mono-de-O-functionalization of disubstituted p-tert-butylcalix[4]arenes using titanium tetrachloride was developed to synthesize a series of monosubstituted p-tert-butylcalix[4]arenes with the pendant functions being ethoxycarbonylmethyloxy, 3-ethoxycarbonylpropyloxy, cyanomethyloxy, 3-cyanopropyloxy, 4-bromobutyloxy, 3-hydroxypropyloxy, propyloxy, 2-methylpropyloxy, 3-butynyloxy, and 3-cyanopropyloxy groups The reaction mechanism of the formation of 5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-ethoxycarbonylpropyloxy) calix[4]arene was studied by H-1 NMR and GC/mass spectroscopy monitoring Reaction of TiCl4 with the disubstituted p-tert-butylcalix[4]arene produced the corresponding dioxocalix[4]arene titanium dichloride complex, which undergoes elimination of ethyl 4-chlorobutyrate, leading to a trioxocalix[4]arene titanium dichloride complex and to monosubstituted calix[4]arene after hydrolysis These two complexes were also synthesized, isolated, and fully characterized

  DOI：

  10.1021/jo101319s