2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl | 909101-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl
• 英文别名: (S)-2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl；(R)-2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl
• CAS: 909101-32-2
• 化学式: C₃₇H₂₄O
• 分子量: 484.597
• InChiKey: LOOCEDCMKXBIBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.76
• 重原子数：
  38.0
• 可旋转键数：
  2.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl 、 右旋樟脑-10-磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以0.018 mg的产率得到((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid 2'-(11H-benzo[b]fluoren-5-yl)-[1,1']binaphthalenyl-2-yl ester
  参考文献：
  名称：

  Synthesis and separation of the atropisomers of 2-(5-benzo[b]fluorenyl)-2′-hydroxy-1,1′-binaphthyl and related compounds

  摘要：

  Several syn and anti atropisomers of 2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl and related compounds were synthesized from 1,1'-binaphthyl-2,2'-diol (BINOL). It was possible to separate the syn and anti atropisomers by silica gel column chromatography. The syn atropisomers are potential hetero-bidentate ligands for complex formation with metals. By starting from enantiomerically pure (R)-(+)-BINOL and (S)-(-)-BINOL, four optically active syn atropisomers and two anti atropisomers with high enantiomeric purity were obtained. The structures of two syn atropisomers and one anti atropisomer were established by X-ray structure analyses. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.004
• 作为产物：
  描述：

  在 potassium tert-butylate 、 三溴化硼 作用下， 以 异丁醇 、 甲苯 、 二氯甲烷 为溶剂， 反应 9.0h， 以42%的产率得到2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  Synthesis and separation of the atropisomers of 2-(5-benzo[b]fluorenyl)-2′-hydroxy-1,1′-binaphthyl and related compounds

  摘要：

  Several syn and anti atropisomers of 2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl and related compounds were synthesized from 1,1'-binaphthyl-2,2'-diol (BINOL). It was possible to separate the syn and anti atropisomers by silica gel column chromatography. The syn atropisomers are potential hetero-bidentate ligands for complex formation with metals. By starting from enantiomerically pure (R)-(+)-BINOL and (S)-(-)-BINOL, four optically active syn atropisomers and two anti atropisomers with high enantiomeric purity were obtained. The structures of two syn atropisomers and one anti atropisomer were established by X-ray structure analyses. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.004