31,32,33,34,35-pentamethoxycalix[5]arene | 205925-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 31,32,33,34,35-pentamethoxycalix[5]arene
• 英文别名: 31,32,33,34,35-Pentamethoxyhexacyclo[25.3.1.13,7.19,13.115,19.121,25]pentatriaconta-1(31),3(35),4,6,9(34),10,12,15(33),16,18,21,23,25(32),27,29-pentadecaene
• CAS: 205925-66-2
• 化学式: C₄₀H₄₀O₅
• 分子量: 600.755
• InChiKey: OEAIYBSEGVPKJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  31,32,33,34,35-pentamethoxycalix[5]arene 在 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Tricalixarenes and Pentacalixarenes:  Synthesis and Complexation Studies¹

  摘要：

  Tricalix[4]arene 4, tricalix[5]arene 14, and pentacalix[4]arene 10 have been synthesized from O-alkylcalixarene mono- and dialdehydes by a two-step conversion to the corresponding monoethynyl ketones or diethynyl ketones followed by aryne trimerization in refluxing DMF containing a dialkylamine. The tricalixarenes 4 and 14 were converted, in turn, to calixarenes 6 and 16, which carry OH groups on the lower rim and methylenes as the bridging moieties to the benzene ring. Complexation studies with the tricalix[5]arene 16 show that it forms (a) a 1:3 complex with N,N-dimethylethylenediamine in which each calixarene unit contains a molecule of the amine, (b) a 1:1 complex with tris(aminomethyl)amine in which each calixarene unit contains one of the three arms of the guest, and (c) a 1:1 complex with C-60 in which the guest presumably resides in the cavity provided by the three calixarene units acting cooperatively.

  DOI：

  10.1021/jo0110808
• 作为产物：
  描述：

  杯[5]芳烃 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以88%的产率得到31,32,33,34,35-pentamethoxycalix[5]arene
  参考文献：
  名称：

  Tricalixarenes and Pentacalixarenes:  Synthesis and Complexation Studies¹

  摘要：

  Tricalix[4]arene 4, tricalix[5]arene 14, and pentacalix[4]arene 10 have been synthesized from O-alkylcalixarene mono- and dialdehydes by a two-step conversion to the corresponding monoethynyl ketones or diethynyl ketones followed by aryne trimerization in refluxing DMF containing a dialkylamine. The tricalixarenes 4 and 14 were converted, in turn, to calixarenes 6 and 16, which carry OH groups on the lower rim and methylenes as the bridging moieties to the benzene ring. Complexation studies with the tricalix[5]arene 16 show that it forms (a) a 1:3 complex with N,N-dimethylethylenediamine in which each calixarene unit contains a molecule of the amine, (b) a 1:1 complex with tris(aminomethyl)amine in which each calixarene unit contains one of the three arms of the guest, and (c) a 1:1 complex with C-60 in which the guest presumably resides in the cavity provided by the three calixarene units acting cooperatively.

  DOI：

  10.1021/jo0110808

文献信息

• Influence of the size of upper and lower rim substituents on the fluxional and complexation behaviour of calix[5]arenes
  作者：George Ferguson、Anna Notti、Sebastiano Pappalardo、Melchiorre F. Parisi、Anthony L. Spek

  DOI：10.1016/s0040-4039(98)00106-3

  日期：1998.4

  via the p-phenyl-through-the-annulus mechanism with ΔG‡ in the range 17.9–18.8 kcal mol−1. Unlike the corresponding tert-butylated counterparts, p-H-calix[5]arenes are unable to form 1:1 endo-calix complexes with primary unbranched alkylammonium cations.

  对一系列五-O-烷基化的对-H-杯[5]芳烃1b-e和对-叔丁基杯[ 5]芳烃1g-m的比较研究表明，前者固有地是可移动的，并且在非-溶液中被采用。圆锥构象。通过单晶X射线分析证明了五-O-苄基醚1c的1，2-交替构象。上VT-NMR研究1C-E所提供的第一实验证据表明通过构象发生相互转化的对-苯基-通过-的-环与ΔG机构‡在17.9–18.8 kcal mol -1的范围内。与相应的叔丁基化对应物不同，p -H-calix [5]芳烃无法与伯直链烷基铵阳离子形成1：1内-calix络合物。