25-Bromo-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-trien-27-ol | 946533-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 25-Bromo-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-trien-27-ol
• 英文别名: 25-bromo-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-trien-27-ol
• CAS: 946533-33-1
• 化学式: C₂₀H₃₁BrO₈
• 分子量: 479.365
• InChiKey: DCTIHSPMSAXHRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  25-Bromo-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-trien-27-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 45.0h， 以75%的产率得到(25-Bromo-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-trien-27-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：

  六甘醇 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 0.75h， 生成 25-Bromo-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-trien-27-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

• Remarkable effect of hydrogen bonding between ring and axle components on deslipping reactions of rotaxanes
  作者：Keiji Hirose、Yamato Nakamura、Hirokazu Takano、Keiji Nishihara、Yoshito Tobe

  DOI：10.1016/j.tetlet.2009.02.179

  日期：2009.7

  A series of rotaxanes 1.5, 2.5, 3.5, and 4.5 bearing a different substituent (X = NO(2), Br, H, and OMe, respectively) at para position on the phenol moiety of the ring component exhibit clear difference in deslipping behavior. The difference in the deslipping rates is consistent with the difference in intercomponent hydrogen bonding strength estimated from the O-H stretching vibration wavenumbers. The para substituent dictates the relative strength of the intra- and intermolecular hydrogen bonds. Thus the incorporation of an intramolecular hydrogen bond allows for tunability of the strength of the intercomponent interaction. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.