1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy[3.3.3]metacyclophane | 1052115-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy[3.3.3]metacyclophane
• 英文别名: 6,14,22-Trimethoxy-2,2,10,10,18,18-hexamethyltetracyclo[19.3.1.15,9.113,17]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaene
• CAS: 1052115-60-2
• 化学式: C₃₆H₄₈O₃
• 分子量: 528.775
• InChiKey: QSLCARZZAWTSBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy[3.3.3]metacyclophane 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到1,1,10,10,19,19-hexamethyl-5,14,23-trihydroxy[3.3.3]metacyclophane
  参考文献：
  名称：

  Facile Preparation and Molecular Structure of a Novel Metacyclophane

  摘要：

  A novel 1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy[3.3.3]metacyclophane (2) was prepared in 25% yield by Friedel-Crafts cyclization of 4-(2-methoxyphenyl)-2-methylbutan-2-ol (1) at -78 degrees C using TiCl(4) as Lewis acid catalyst in anhydrous dichloromethane. The structure of cyclophane 2 was determined by single-crystal X-ray diffraction, and the impact of substrate concentration on the yield of macrocycle 2 was also examined. The study on the effect of substituents at the phenyl ring showed that the methoxy group in 1 is crucial for its trimerization to give the hexamethyl[3.3.3]metacyclophane derivative. Demethylation of 2 with BBr(3) gave 1,1,10,10,19,19-hexamethyl-5,14,23-trihydroxy[3.3.3]metacyclophane (4) in 96% yield, and its three hydroxyl groups provide the possible modification sites for further construction of supramolecular assemblies.

  DOI：

  10.1080/00397910802138645
• 作为产物：
  描述：

  4-(2-methoxyphenyl)-2-methylbutan-2-ol 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy[3.3.3]metacyclophane
  参考文献：
  名称：

  Facile Preparation and Molecular Structure of a Novel Metacyclophane

  摘要：

  A novel 1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy[3.3.3]metacyclophane (2) was prepared in 25% yield by Friedel-Crafts cyclization of 4-(2-methoxyphenyl)-2-methylbutan-2-ol (1) at -78 degrees C using TiCl(4) as Lewis acid catalyst in anhydrous dichloromethane. The structure of cyclophane 2 was determined by single-crystal X-ray diffraction, and the impact of substrate concentration on the yield of macrocycle 2 was also examined. The study on the effect of substituents at the phenyl ring showed that the methoxy group in 1 is crucial for its trimerization to give the hexamethyl[3.3.3]metacyclophane derivative. Demethylation of 2 with BBr(3) gave 1,1,10,10,19,19-hexamethyl-5,14,23-trihydroxy[3.3.3]metacyclophane (4) in 96% yield, and its three hydroxyl groups provide the possible modification sites for further construction of supramolecular assemblies.

  DOI：

  10.1080/00397910802138645

文献信息

• Facile Preparation and Molecular Structure of a Novel Metacyclophane
  作者：Jing-Lei Zhang、Qi Shi、Jiang Wu、Yang Wang

  DOI：10.1080/00397910802138645

  日期：2008.6.27

  A novel 1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy[3.3.3]metacyclophane (2) was prepared in 25% yield by Friedel-Crafts cyclization of 4-(2-methoxyphenyl)-2-methylbutan-2-ol (1) at -78 degrees C using TiCl(4) as Lewis acid catalyst in anhydrous dichloromethane. The structure of cyclophane 2 was determined by single-crystal X-ray diffraction, and the impact of substrate concentration on the yield of macrocycle 2 was also examined. The study on the effect of substituents at the phenyl ring showed that the methoxy group in 1 is crucial for its trimerization to give the hexamethyl[3.3.3]metacyclophane derivative. Demethylation of 2 with BBr(3) gave 1,1,10,10,19,19-hexamethyl-5,14,23-trihydroxy[3.3.3]metacyclophane (4) in 96% yield, and its three hydroxyl groups provide the possible modification sites for further construction of supramolecular assemblies.