4,6,10,12,16,18,22,24-octamethylpentacyclo<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-dodecaene-25,26,27,28-tetrol | 123775-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4,6,10,12,16,18,22,24-octamethylpentacyclo<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-dodecaene-25,26,27,28-tetrol
• 英文别名: 4,6,10,12,16,18,22,24-Octamethyl-25,26,27,28-tetrahydroxycalix<4>arene；4,6,10,12,16,18,22,24-Octamethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-25,26,27,28-tetrol
• CAS: 123775-99-5
• 化学式: C₃₆H₄₀O₄
• 分子量: 536.711
• InChiKey: XQILYXQBYSQBQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  40
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6,10,12,16,18,22,24-octamethylpentacyclo<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-dodecaene-25,26,27,28-tetrol 、 硫酸二甲酯 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 以37%的产率得到26,28-Dimethoxy-4,6,10,12,16,18,22,24-octamethylpentacyclo<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-dodecene-25,27-diol
  参考文献：
  名称：

  Stereodynamics of 4,6,10,12,16,18,22,24-octamethylcalix[4]arene

  摘要：

  The dynamic stereochemistry of 4,6,10,12,16,18,22,24-octamethyl-25,26,27,28-tetrahydroxycalix[4]arene (2) is analyzed. The measured barrier for the coalescence of the diastereotropic methylene protons (10.9 kcal mol-1) and the coalescence of the methyl signals (10.7 kcal mol-1) is identical. It is concluded that the dynamic pathway observed by NMR corresponds to a ring-inversion process which exchanges both the methylene protons and the symmetry nonequivalent "perpendicular" and "coplanar" aryl rings. Molecular mechanics calculations satisfactorily reproduce the boat conformation of 2 and indicate that the presumed transition state for the pseudorotation process lies 27 kcal mol-1 above the ground state. In contrast to the parent p-tert-butylcalix[4]arene (1), changing the solvent from CDCl3 to pyridine-d5 raises the inversion barrier of 2. Calixarene 2 crystallizes from pyridine as a 1:1 complex in which the calixarene molecular exists in a boat conformation and the pyridine molecule is partially included in the calix cavity. Fixation of the conformation of 2 was obtained by preparing the 1,3-dimethyl ether derivative 6 by alkylation of 2 under phase-transfer catalysis conditions. The conformation of 6 in the crystal is similar to that of 2, with the two methoxy groups located in the "perpendicular" rings. The inversion barrier of 6 is higher than 24.0 kcal mol-1 as estimated by saturation transfer experiments.

  DOI：

  10.1021/jo00026a016
• 作为产物：
  描述：

  4-羟基-2,6-二甲基苯甲醇 在 三氯化铝 作用下， 以 硝基苯 为溶剂， 反应 2.0h， 以28%的产率得到4,6,10,12,16,18,22,24-octamethylpentacyclo<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-dodecaene-25,26,27,28-tetrol
  参考文献：
  名称：

  Octamethylcalix[4]arene

  摘要：

  DOI：

  10.1021/jo00287a002