dimethoxypillar[7]arene | 1375870-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: dimethoxypillar[7]arene
• CAS: 1375870-08-8
• 化学式: C₆₃H₇₀O₁₄
• 分子量: 1051.24
• InChiKey: LJCMTVDPXQNDOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.26
• 重原子数：
  77.0
• 可旋转键数：
  14.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  129.22
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  dimethoxypillar[7]arene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以82%的产率得到per-hydroxylated pillar[7]arene
  参考文献：
  名称：

  Synthesis of pillar[7]arene

  摘要：

  The first synthesis of pillar[7]arene is reported with two methods. Method A: the FeCl3-catalyzed condensation reaction of 1,4-dimethoxybenzene (1) with paraformaldehyde in CHCl3 gave dimethoxypillar[7]arene (3). Method B: the p-toluenesulfonic acid catalyzed condensation reaction of 2,5-bis(benzyloxymethyl)-1,4-dimethoxybenzene (2) in CH2Cl2 gave compound 3. Demethylation of 3 with BBr3 gave pillar[7]arene (4). The pillar[7]arene might be a perspective macrocyclic host in host-guest chemistry. (C) 2012 De Rong Cao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.03.026
• 作为产物：
  描述：

  对苯二甲醚 、 alkaline earth salt of/the/ methylsulfuric acid 在 iron(III) chloride 作用下， 以 氯仿 为溶剂， 以6.8%的产率得到dimethoxypillar[7]arene
  参考文献：
  名称：

  Synthesis of pillar[7]arene

  摘要：

  The first synthesis of pillar[7]arene is reported with two methods. Method A: the FeCl3-catalyzed condensation reaction of 1,4-dimethoxybenzene (1) with paraformaldehyde in CHCl3 gave dimethoxypillar[7]arene (3). Method B: the p-toluenesulfonic acid catalyzed condensation reaction of 2,5-bis(benzyloxymethyl)-1,4-dimethoxybenzene (2) in CH2Cl2 gave compound 3. Demethylation of 3 with BBr3 gave pillar[7]arene (4). The pillar[7]arene might be a perspective macrocyclic host in host-guest chemistry. (C) 2012 De Rong Cao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.03.026

文献信息

• Synthesis and inclusion properties of pillar[n]arenes
  作者：Yuhui Kou、Derong Cao、Hongqi Tao、Lingyun Wang、Jianquan Liang、Zhizhao Chen、Herbert Meier

  DOI：10.1007/s10847-012-0242-5

  日期：2013.12

  A detailed study of the reaction conditions revealed that a quantitative cyclocondensation of 1,4-dialkoxy-2,5-bis(alkoxymethyl)-benzenes to pillar[n]arenes can be achieved by catalysis of p-toluenesulfonic acid in CH2Cl2. Major product of this new reaction is in each case a cyclopentamer (n = 5), but small amounts of the pillar[n]arenes with n = 6, 7 and 10 can be obtained as well. Different alkoxy groups in 1- and 4-position lead to regioisomers. All cyclooligomers exist in pillar structures as pair of enantiomers, which show a racemisation at room temperature, which is fast in terms of the NMR time scale. The racemisation process occurs by rotation of the 1,4-phenylene segments in the macrocyclic rings. Pillar[n]arenes exhibit novel host–guest behavior.

  对反应条件的详细研究表明，在对甲苯磺酸在 CH2Cl2 中的催化作用下，可以将 1,4-二烷氧基-2,5-双（烷氧基甲基）苯定量环缩合为柱[n]烷。这种新反应的主要产物都是环五聚物（n = 5），但也可以得到少量 n = 6、7 和 10 的柱[n]烷。1 位和 4 位上的烷氧基不同，会产生区域异构体。所有环醇异构体都以一对对映体的形式存在于柱状结构中，在室温下会发生消旋化，从核磁共振时间尺度来看，消旋化速度很快。外消旋过程是通过大环中的 1,4-亚苯基段旋转而发生的。柱[n]烷表现出新颖的宿主-宾客行为。