r-2,c-8,c-14,c-20-tetra(carbomethoxymethyl)pentacyclo<19.3.1.1^3,7.1^9,13.1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol, octamethyl ether | 140111-46-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: r-2,c-8,c-14,c-20-tetra(carbomethoxymethyl)pentacyclo<19.3.1.1^3,7.1^9,13.1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol, octamethyl ether
• 英文别名: r-2,c-8,c-14,c-20-tetra(carbomethoxymethyl)pentacyclo<19.3.1.1^3,7.1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol octamethyl ether
• CAS: 140111-46-2
• 化学式: C₄₈H₅₆O₁₆
• 分子量: 888.963
• InChiKey: ZIDXCQXCUNJMOS-KMKVIZFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.85
• 重原子数：
  64.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  179.04
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  r-2,c-8,c-14,c-20-tetra(carbomethoxymethyl)pentacyclo<19.3.1.1^3,7.1^9,13.1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol, octamethyl ether 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 r-2,c-8,c-14,c-20-tetra(hydroxyethyl)pentacyclo<19.3.1.1^3,7.1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol octamethyl ether
  参考文献：
  名称：

  A Novel Route to Calix[4]arenes. 2. Solution- and Solid-State Structural Analyses and Molecular Modeling Studies

  摘要：

  A versatile route to a series of C-alkylcalix[4]resorcinarenes has been developed, using 2,4-dimethoxycinnamates as starting materials under carefully controlled reaction conditions employing BF3 as a Lewis acid catalyst. Depending on the reaction conditions and the nature of the ester side chain in the cinnamates, the calixarenes can adopt 1,2-alternate, 1,3-alternate, or flattened-cone conformational states. An extensive study, relating to the influence of the Lewis acid, temperature, and reaction time, has provided information on the relative ratios of the different conformations and their interconversion. Structural assignments are based on detailed spectroscopic analyses including X-ray analyses. The latter provide evidence of their molecular structure and shape in the solid state. A detailed molecular modeling study has been completed and is described. From the data obtained, good agreement with NMR data, X-ray analyses and experimental results is observed.

  DOI：

  10.1021/jo00085a047
• 作为产物：
  描述：

  (E)-3-(2,4-dimethoxy-phenyl)-acrylic acid methyl ester 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 r-2,c-8,t-14,t-20-tetra(carbomethoxymethyl)pentacyclo<19.3.1.1^3,7.1^9,13.1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol, octamethyl ether 、 r-2,c-8,c-14,c-20-tetra(carbomethoxymethyl)pentacyclo<19.3.1.1^3,7.1^9,13.1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol, octamethyl ether
  参考文献：
  名称：

  The tetramerization of 2,4-dimethoxycinnamates. A novel route to calixarenes

  摘要：

  Treatment of (E)-2,4-dimethoxycinnamic acid methyl ester with BF3.Et2O in CHCl3 at room temperature afforded in 75% yield two stereoisomeric C-alkylcalix[4]resorcinarenes, which were shown to be in the 1,2-alternate and flattened-cone configurations.

  DOI：

  10.1021/jo00038a001