tetrakis-O-(diethoxyphosphoryl)-p-tert-butylcalix[4]arene | 128910-40-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: tetrakis-O-(diethoxyphosphoryl)-p-tert-butylcalix[4]arene
• 英文别名: 25,26,27,28-tetrakis-O-(diethoxyphosphoryl)(p-tert-butyl)calix[4]arene；Diethyl [5,11,17,23-tetratert-butyl-26,27,28-tris(diethoxyphosphoryloxy)-25-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-dodecaenyl] phosphate
• CAS: 128910-40-7
• 化学式: C₆₀H₉₂O₁₆P₄
• 分子量: 1193.28
• InChiKey: ZWBGNSWYZHTNCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15
• 重原子数：
  80
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  179
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  tetrakis-O-(diethoxyphosphoryl)-p-tert-butylcalix[4]arene 在 三氯化铝 、 氨 、 甲苯 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 五环[19.3.1.13,7.19,13.115,19]二十八-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-十二烯
  参考文献：
  名称：

  未取代的杯[4]芳烃的合成与构象

  摘要：

  制备标题化合物，并通过单晶X射线衍射法研究其结构。发现处于结晶状态的分子构象与先前报道的取代杯[4]芳烃的构象不同。分子力学计算表明，晶体中的构象不代表最小能量。

  DOI：

  10.1016/s0040-4039(00)93521-4
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 、 氯磷酸二乙酯 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以57%的产率得到tetrakis-O-(diethoxyphosphoryl)-p-tert-butylcalix[4]arene
  参考文献：
  名称：

  杯芳烃二乙基磷酸酯的多重还原裂解：[1 n ]间环phanes的途径

  摘要：

  的OH基团p -t丁基杯[ Ñ ]芳烃（Ñ = 4和8）转化成二乙基磷酸酯和还原断裂通过用K / NH 3，得到四- p -叔丁基[1 4 ] -和八-对-叔丁基[1 8 ]亚甲基环（4）和（7）。

  DOI：

  10.1039/p19900001484

文献信息

• Selectively dehydroxylated calix[4]arenes and 1,3-dithiocalix[4]arenes; novel classes of calix[4]arenes
  作者：Yuhua Ting、Willem Verboom、Leo C. Groenen、Jan-Dirk van Loon、David N. Reinhoudt

  DOI：10.1039/c39900001432

  日期：——

  Selective modification of calix[4]arenes either by selective dehydroxylation via the reductive removal of phosphate(s), or via the Newman–Kwart rearrangement of 1,3-bis(dimethylthiocarbamoyl)calix[4]arenes yields calix[4]arenes 3 and 1,3-dithiocalix[4]arenes 6, respectively.

  杯[4]芳烃的选择性修饰，可以通过磷酸盐的还原去除或通过1,3-双（二甲基硫代氨基甲酰基）杯[4]芳烃的Newman-Kwart重排而进行选择性脱羟基，从而产生杯[4]芳烃3和1,3-二硫杂杯[4]芳烃6。
• Symmetrical and inherently chiral water-soluble calix[4]arenes bearing dihydroxyphosphoryl groups
  作者：Maxim A. Tairov、Myroslav O. Vysotsky、Olga I. Kalchenko、Vladimir V. Pirozhenko、Vitaly I. Kalchenko

  DOI：10.1039/b110691k

  日期：2002.5.23

  A series of symmetrical and inherently chiral water-soluble calix[4]arenes bearing one, two or four proton-ionisable dihydroxyphosphoryl groups at the narrow rim of the macrocycle has been synthesised by consecutive treatment of appropriate diethoxyphosphoryl derivatives with bromotrimethylsilane and methanol. The calix[4]arene phosphoric acids synthesised possess pKa-values 2.85–3.10 (CH3OH–H2O 70 : 30) and form salts with L-(−)-α-phenylethylamine or (1S,2R)-(+)-ephedrine in methanol solution. The salts of the inherently chiral calixarene phosphoric acids with chiral amines are easily separated into diastereomeric forms by the RP HPLC method on Separon SGX C18 or Partisil 5 ODS 3 achiral columns.

  通过用溴化三甲基硅烷和甲醇连续处理适当的二乙氧基磷衍生物，合成了一系列对称的、固有手性的水溶性钙[4]烯，这些钙[4]烯在大环的窄边上带有一个、两个或四个可质子离子化的二羟基磷基。合成的钙[4]炔磷酸的 pKa 值为 2.85-3.10（CH3OH-H2O 70：30），并在甲醇溶液中与 L-(-)-α-苯乙胺或 (1S,2R)-(+)-麻黄碱形成盐。在 Separon SGX C18 或 Partisil 5 ODS 3 非手性色谱柱上采用 RP HPLC 方法，可以轻松地将固有手性的钙烯烃磷酸盐与手性胺分离成非对映异构体。
• Phosphorylated-calix[4]arene double-deckers of single rare earth metal ions
  作者：Marjan Hosseinzadeh、Sergio Sanz、Jan van Leusen、Natalya V. Izarova、Euan K. Brechin、Scott J. Dalgarno、Paul Kögerler

  DOI：10.1039/d1cc02910j

  日期：——

  Combination of phosphoryl and calix[4]arene moieties in the same organic framework (LPO) directs the formation of homoleptic double–decker complexes [LnIII(LPO)2](OTf)3 for Ln = Tb and Dy, with the latter displaying slow relaxation of the magnetisation.

  磷酰基和杯[4]芳烃部分在同一有机骨架 (L PO ) 中的组合指导形成均配双层复合物 [Ln III (L PO ) 2 ](OTf) 3，其中 Ln = Tb 和 Dy，其中后者显示出磁化的缓慢弛豫。
• Phase Solubility Studies of Poorly Soluble Drug Molecules by Using <i>O</i>-Phosphorylated Calixarenes as Drug-Solubilizing Agents
  作者：Mevlüt Bayrakcı、Şeref Ertul、Mustafa Yilmaz

  DOI：10.1021/je200992c

  日期：2012.1.12

  This study is the first report on the solubilizing effect of O-phosphorylated calix[n]arenes that form complexes with neutral molecules such as nifedipine, niclosamide, and furosemide by host-guest complexation. These complexation studies were carried out by using the phase solubility technique. From the obtained results, it was observed that the solubility of guest molecules such as nifedipine, niclosamide, and furosemide was significantly increased in the presence of host molecules tetrakis-O-(diethoxyphosphoryl)-p-tert-butylcalix[4]arene (1), tetrakis-O-(diethoxyphosphoryl)-calix[4]arene (2), bis-O-(diethoxyphosphoryl)-p-tert-butylcalix[4]arene (3), bis-O-(diethoxyphosphoryl)-calix[4]arene (4), and octakis-O-(diethoxyphosphoryl)-p-tert-butylcalix[8]arene (5). The increase in solubility of drugs by the calixarene host 1 to 5 was most probably due to inclusion complexation between drug molecules and cavities of the calixarene skeleton similar to drug-cyclodextrin complexes.
• Harrowfield, Jack M.; Mocerino, Mauro; Peachey, Brendan J., Journal of the Chemical Society, Dalton Transactions, 1996, p. 1687 - 1700
  作者：Harrowfield, Jack M.、Mocerino, Mauro、Peachey, Brendan J.、Skelton, Brian W.、White, Allan H.

  DOI：——

  日期：——