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

文献信息

• New potential prodrugs of aciclovir using calix[4]arene as a lipophilic carrier: synthesis and drug-release studies at the air–water interface
  作者：Guillaume Sautrey、Igor Clarot、Ewa Rogalska、Jean-Bernard Regnouf-de-Vains

  DOI：10.1039/c2nj40338b

  日期：——

  Two tetra-p-tert-butyl-calix[4]arene species bearing one or two anti-HSV aciclovir units tethered via carbodiester linkages at the lower rim were synthesized as possible antiviral prodrugs. The amphiphilic properties of these derivatives were studied using Langmuir balance at the air–water and air–carbonate buffer interfaces; the monolayers formed were stable on both subphases. Monolayers formed with these molecules on a carbonate buffer subphase at pH 10 and 37 °C were then used for monitoring hydrolysis of the diester linkage. The release of free aciclovir of around 30% in 3 days was observed with both derivatives, as shown with HPLC.

  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。
• Easy and Selective Method for the Synthesis of Various Mono-<i>O</i>-functionalized Calix[4]arenes: De-<i>O</i>-functionalization Using TiCl₄
  作者：Joackim Bois、Jeff Espinas、Ulrich Darbost、Caroline Felix、Christian Duchamp、Denis Bouchu、Mostafa Taoufik、Isabelle Bonnamour

  DOI：10.1021/jo101319s

  日期：2010.11.19

  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