6,6'-dibromo-3,3'-diphenyl-1,1'-bi-2-naphthol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,6'-dibromo-3,3'-diphenyl-1,1'-bi-2-naphthol
• 英文别名: (R)-6,6'-dibromo-3,3'-diphenyl-1,1'-binaphthol；6-Bromo-1-(6-bromo-2-hydroxy-3-phenylnaphthalen-1-yl)-3-phenylnaphthalen-2-ol
• 化学式: C₃₂H₂₀Br₂O₂
• 分子量: 596.318
• InChiKey: MLVDSUCIBOKXBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,6'-dibromo-3,3'-diphenyl-1,1'-bi-2-naphthol 在 吡啶 、 三氯氧磷 、 水 、 碳酸氢钠 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以57%的产率得到(R)-6,6'-dibromo-3,3'-diphenyl-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
  参考文献：
  名称：

  EP1623971

  摘要：

  公开号：
• 作为产物：
  描述：

  (R)-3,3'-二苯基-1,1'-联萘酚 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到6,6'-dibromo-3,3'-diphenyl-1,1'-bi-2-naphthol
  参考文献：
  名称：

  Chiral Catalyst Optimization Using Both Solid-Phase and Liquid-Phase Methods in Asymmetric Aza Diels−Alder Reactions

  摘要：

  In the presence of 1-5 mol % of a chiral zirconium catalyst, aza Diels-Alder reactions of aldimines with Danisheisky's dienes proceeded smoothly to afford the corresponding piperidine derivatives in high yields with high enantioselectivities. For the catalyst optimization, solid-phase and liquid-phase methods were successfully used. In the solid-phase approach, polymer-supported (R)-1,1'-binaphthols (BINOLs) have been synthesized and rapid optimization using the solid-phase reactions has been achieved. On the other hand, novel chiral zirconium cyanides were developed as excellent catalysts using the liquid-phase approach.

  DOI：

  10.1021/ol005656b
• 作为试剂：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 (E)-N-(2-methylbenzylidene)-2-hydroxyaniline 在 6,6'-dibromo-3,3'-diphenyl-1,1'-bi-2-naphthol 、 N-甲基咪唑 、 zirconium(IV) tert-butoxide 作用下， 以 苯 为溶剂， 生成 (R)-1-(2-Hydroxy-phenyl)-2-o-tolyl-2,3-dihydro-1H-pyridin-4-one 、 (S)-1-(2-Hydroxy-phenyl)-2-o-tolyl-2,3-dihydro-1H-pyridin-4-one
  参考文献：
  名称：

  A Switch of Enantiofacial Selectivities Using Designed Similar Chiral Ligands in Zirconium-Catalyzed Asymmetric Aza Diels−Alder Reactions

  摘要：

  DOI：

  10.1021/jo9902300

文献信息

• EP1623971
  申请人：——

  公开号：——

  公开（公告）日：——
• Chiral Catalyst Optimization Using Both Solid-Phase and Liquid-Phase Methods in Asymmetric Aza Diels−Alder Reactions
  作者：Shū Kobayashi、Ken-ichi Kusakabe、Haruro Ishitani

  DOI：10.1021/ol005656b

  日期：2000.5.1

  In the presence of 1-5 mol % of a chiral zirconium catalyst, aza Diels-Alder reactions of aldimines with Danisheisky's dienes proceeded smoothly to afford the corresponding piperidine derivatives in high yields with high enantioselectivities. For the catalyst optimization, solid-phase and liquid-phase methods were successfully used. In the solid-phase approach, polymer-supported (R)-1,1'-binaphthols (BINOLs) have been synthesized and rapid optimization using the solid-phase reactions has been achieved. On the other hand, novel chiral zirconium cyanides were developed as excellent catalysts using the liquid-phase approach.