22-Bromo-3,6,9,12,15,18-hexaoxabicyclo[18.3.1]tetracosa-1(23),20(24),21-trien-24-ol | 946533-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 22-Bromo-3,6,9,12,15,18-hexaoxabicyclo[18.3.1]tetracosa-1(23),20(24),21-trien-24-ol
• 英文别名: 22-bromo-3,6,9,12,15,18-hexaoxabicyclo[18.3.1]tetracosa-1(23),20(24),21-trien-24-ol
• CAS: 946533-31-9
• 化学式: C₁₈H₂₇BrO₇
• 分子量: 435.312
• InChiKey: CEZDASNQQRIIKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  22-Bromo-3,6,9,12,15,18-hexaoxabicyclo[18.3.1]tetracosa-1(23),20(24),21-trien-24-ol 、 3,5-二硝基苯甲酰氯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到(22-Bromo-3,6,9,12,15,18-hexaoxabicyclo[18.3.1]tetracosa-1(23),20(24),21-trien-24-yl) 3,5-dinitrobenzoate
  参考文献：
  名称：

  Highly Selective and High-Yielding Rotaxane Synthesis via Aminolysis of Prerotaxanes Consisting of a Ring Component and a Stopper Unit

  摘要：

  A highly rotaxane-selective synthesis via aminolysis of prerotaxanes, which were composed of a phenolic pseudo-crown ether as a ring component and a bulky stopper unit, was developed. The best result was obtained in the case of aminolysis of 3b with 3,5-dimethylbenzylamine which proceeded quantitatively with ca. 100% rotaxane selectivity forming the corresponding rotaxane 5b. The rotaxanes were formed by kinetically controlled attack of the amine from the backside of the ring component of the prerotaxanes.

  DOI：

  10.1021/ol070999w
• 作为产物：
  描述：

  5-溴-1,3-二(溴甲基)-2-甲氧基苯 在 sodium hydride 、 乙硫醇 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 22-Bromo-3,6,9,12,15,18-hexaoxabicyclo[18.3.1]tetracosa-1(23),20(24),21-trien-24-ol
  参考文献：
  名称：

  Highly Selective and High-Yielding Rotaxane Synthesis via Aminolysis of Prerotaxanes Consisting of a Ring Component and a Stopper Unit

  摘要：

  A highly rotaxane-selective synthesis via aminolysis of prerotaxanes, which were composed of a phenolic pseudo-crown ether as a ring component and a bulky stopper unit, was developed. The best result was obtained in the case of aminolysis of 3b with 3,5-dimethylbenzylamine which proceeded quantitatively with ca. 100% rotaxane selectivity forming the corresponding rotaxane 5b. The rotaxanes were formed by kinetically controlled attack of the amine from the backside of the ring component of the prerotaxanes.

  DOI：

  10.1021/ol070999w

文献信息

• Highly Selective and High-Yielding Rotaxane Synthesis via Aminolysis of Prerotaxanes Consisting of a Ring Component and a Stopper Unit
  作者：Keiji Hirose、Keiji Nishihara、Naoki Harada、Yamato Nakamura、Daisuke Masuda、Masami Araki、Yoshito Tobe

  DOI：10.1021/ol070999w

  日期：2007.8.1

  A highly rotaxane-selective synthesis via aminolysis of prerotaxanes, which were composed of a phenolic pseudo-crown ether as a ring component and a bulky stopper unit, was developed. The best result was obtained in the case of aminolysis of 3b with 3,5-dimethylbenzylamine which proceeded quantitatively with ca. 100% rotaxane selectivity forming the corresponding rotaxane 5b. The rotaxanes were formed by kinetically controlled attack of the amine from the backside of the ring component of the prerotaxanes.