(5S,19S)-25-bromo-27-methoxy-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene | 548485-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5S,19S)-25-bromo-27-methoxy-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene
• CAS: 548485-22-9
• 化学式: C₃₃H₄₁BrO₈
• 分子量: 645.588
• InChiKey: KWGQMBYFTOTQEN-ROJLCIKYSA-N

物化性质

• 沸点：
  766.3±60.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5S,19S)-25-bromo-27-methoxy-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene 在 正丁基锂 、 水 作用下， 以62%的产率得到(5S,19S)-27-methoxy-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene
  参考文献：
  名称：

  通过使用手性冠醚和podand手性识别仲胺

  摘要：

  制备了具有伪24冠8环的手性冠醚（S，S）-3和手性podand（R，R）-4，它们都对仲胺N -α-二甲基苄胺具有良好的手性识别能力（15）和心得安（16）。

  DOI：

  10.1016/s0040-4039(02)02030-0
• 作为产物：
  描述：

  2,2'-(((1S,1'S)-(((5-bromo-2-methoxy-1,3-phenylene)bis(methylene))bis(oxy))bis(1-phenylethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) 在 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 生成 (5S,19S)-25-bromo-27-methoxy-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene
  参考文献：
  名称：

  Preparation of phenolic chiral crown ethers and podands and their enantiomer recognition ability toward secondary amines

  摘要：

  Phenolic pseudo-24-crown-8 (S,S)-3, pseudo-27-crown-9 (S,S)-4, and podands (R,R)-5 and (R,R)-6 possessing phenyl groups as chiral barriers were prepared and their chiral recognition properties toward secondary neutral amines were examined. Pseudo-24-crown-8 (S,S)-3 and podand (R,R)-5 showed sufficient binding ability and moderate chiral recognition ability toward secondary amines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00031-4

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.