(R)-3,3'-bis(3-trifluoromethylphenyl)-2,2'-dihydroxy-[1,1']binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-3,3'-bis(3-trifluoromethylphenyl)-2,2'-dihydroxy-[1,1']binaphthyl
• 英文别名: (R)-(+)-3,3'-bis(3-(trifluoromethyl)phenyl)-[1,1'-binaphthalene]-2,2'-diol；1-[2-Hydroxy-3-[3-(trifluoromethyl)phenyl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]naphthalen-2-ol
• 化学式: C₃₄H₂₀F₆O₂
• 分子量: 574.522
• InChiKey: GEMBXJWQNXTBKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-3,3'-bis(3-trifluoromethylphenyl)-2,2'-dihydroxy-[1,1']binaphthyl 在 溴 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-6,6'-dibromo-3,3'-bis(3-trifluoromethylphenyl)-2,2'-dihydroxy-[1,1']binaphthyl
  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
• 作为产物：
  描述：

  (R)-3,3'-dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 在 四(三苯基膦)钯 盐酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 20.17h， 生成 (R)-3,3'-bis(3-trifluoromethylphenyl)-2,2'-dihydroxy-[1,1']binaphthyl
  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

文献信息

• Double-Fold Ortho and Remote C–H Bond Activation/Borylation of BINOL: A Unified Strategy for Arylation of BINOL
  作者：Ranjana Bisht、Jagriti Chaturvedi、Gajanan Pandey、Buddhadeb Chattopadhyay

  DOI：10.1021/acs.orglett.9b02347

  日期：2019.8.16

  double-fold ortho and remote C–H borylation of BINOL is described. The proposed mechanisms involved electrostatically and sterically directed ortho and remote C–H activation processes, respectively. While B2eg2 (eg = ethylene glycolate) directs the C–H activation at ortho positions, a combination of HBpin and B2pin2 activates remote C–H bonds. The strategy was combined with Suzuki arylation as a one-pot

  描述了双酚的邻位和邻位双倍硼氢化。拟议的机制分别涉及静电和空间定向的邻位和远程C–H活化过程。虽然B 2 eg 2（例如=乙二醇酯）将CH-H激活在邻位，但HBpin和B 2 pin 2的组合激活了远程CH-H键。该策略与Suzuki芳基化结合在一起，作为一锅操作方案，可快速合成具有手性的BINOL衍生物。
• 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.