(S)-diethyl 6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylate | 1590452-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-diethyl 6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylate
• 英文别名: Ethyl 7-bromo-4-(6-bromo-3-ethoxycarbonyl-2-hydroxynaphthalen-1-yl)-3-hydroxynaphthalene-2-carboxylate；ethyl 7-bromo-4-(6-bromo-3-ethoxycarbonyl-2-hydroxynaphthalen-1-yl)-3-hydroxynaphthalene-2-carboxylate
• CAS: 1590452-74-6
• 化学式: C₂₆H₂₀Br₂O₆
• 分子量: 588.249
• InChiKey: MZPNGVKUXBYIEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-羟基-7-溴-2-萘甲酸乙酯 在 2,2,6,6-四甲基哌啶氧化物 、 氧气 、 [1,1’-联萘]-2,2’-二胺 、 copper(l) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以88%的产率得到(S)-diethyl 6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylate
  参考文献：
  名称：

  铜-（R）-1,1'-联萘-2,2'-二胺-TEMPO催化剂对2-萘酚衍生物的对映选择性氧化偶联

  摘要：

  AbstractAn efficient chiral copper catalytic system [(R)‐(+)‐1,1′‐binaphthyl‐2,2′‐diamine‐copper(I) chloride‐TEMPO] for the asymmetric oxidative coupling of 2‐naphthol derivatives to synthesize enantiomerically enriched BINOL derivatives has been developed with good to excellent enantiomeric excess (up to 97% ee). The addition of a catalytic quantity of 2,2,6,6‐tetramethylpiperidin‐1‐yl oxyl (TEMPO) to the copper‐(R)‐(+)‐1,1′‐binaphthyl‐2,2′‐diamine complex greatly enhanced the reactivity and enantioselectivity of the enantioselective oxidative coupling of 2‐naphthol derivatives and also reduced the reaction temperature from 90 °C to room temperature in dichloromethane solvent.magnified image

  DOI：

  10.1002/adsc.201300513

文献信息

• Enantioselective Oxidative Coupling of 2-Naphthol Derivatives by Copper-(<i>R</i>)-1,1′-Binaphthyl-2,2′-diamine-TEMPO Catalyst
  作者：Santosh Kumar Alamsetti、Elamvazhuthi Poonguzhali、Dhandapani Ganapathy、Govindasamy Sekar

  DOI：10.1002/adsc.201300513

  日期：2013.10.11

  AbstractAn efficient chiral copper catalytic system [(R)‐(+)‐1,1′‐binaphthyl‐2,2′‐diamine‐copper(I) chloride‐TEMPO] for the asymmetric oxidative coupling of 2‐naphthol derivatives to synthesize enantiomerically enriched BINOL derivatives has been developed with good to excellent enantiomeric excess (up to 97% ee). The addition of a catalytic quantity of 2,2,6,6‐tetramethylpiperidin‐1‐yl oxyl (TEMPO) to the copper‐(R)‐(+)‐1,1′‐binaphthyl‐2,2′‐diamine complex greatly enhanced the reactivity and enantioselectivity of the enantioselective oxidative coupling of 2‐naphthol derivatives and also reduced the reaction temperature from 90 °C to room temperature in dichloromethane solvent.magnified image