(S)-4,4'-bis(4-tolyl)-1,1'-binaphthyl-2,2'-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-4,4'-bis(4-tolyl)-1,1'-binaphthyl-2,2'-diol
• 英文别名: 4,4'-di-p-tolyl[1,1'-binaphthalene]-2,2'-diol；1-[2-hydroxy-4-(4-methylphenyl)naphthalen-1-yl]-4-(4-methylphenyl)naphthalen-2-ol
• 化学式: C₃₄H₂₆O₂
• 分子量: 466.579
• InChiKey: BLITWYXSUUPVNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (S)-4,4'-bis(4-tolyl)-1,1'-binaphthyl-2,2'-diol 在 L-脯氨酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以58%的产率得到4,4'-di-p-tolyl[1,1'-binaphthalene]-2,2'-diol
  参考文献：
  名称：

  Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones

  摘要：

  The reaction of 2-(trimethylsilyl) phenyl triflate with aroylacetones in the presence of CsF gave the corresponding 4-aryl-2-naphthols. Substituted triflates also reacted with aroylacetones to afford 4-aryl-2-naphthols regioselectively. The enantioselective oxidation of 4aryl-2-naphthols with a chiral tridentate oxovanadium(IV) complex furnished the corresponding 4,4'-biaryl-1,1'-binaphthols in good yields.

  DOI：

  10.1055/s-0034-1380452
• 作为产物：
  描述：

  4-(p-tolyl)naphthalen-2-ol 在 C₃₄H₃₄N₂O₁₀V₂ 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以82%的产率得到(S)-4,4'-bis(4-tolyl)-1,1'-binaphthyl-2,2'-diol
  参考文献：
  名称：

  通过单和双2-萘酚激活模式逆转BINOL的对映选择性方法

  摘要：

  首次描述了通过机制驱动的2-萘酚衍生物催化不对称氧化偶联的手性1,1'-bi-2-萘酚的对映异构方法。通过利用具有低氧化电位的2-萘酚衍生物，可以通过手性单核或双核钒（V）催化剂活化底物，从而促进明显不同的不对称反应途径：单底物活化和双底物活化机制。

  DOI：

  10.1021/acs.orglett.7b01734

文献信息

• Atropisomerism of the C-1−C‘-1 Axis of 2,2‘,8,8‘-Unsubstituted 1,1‘-Binaphthyl Derivatives
  作者：Hak-Fun Chow、Chi-Wai Wan

  DOI：10.1021/jo0100289

  日期：2001.7.1

  Suzuki coupling of optically active (S)-binaphthyl bromide 10 with (S)-binaphthyl boronic acid 11 produced a diastereomeric mixture of tetrahydroxyquaternaphthyls 4. The coupling products 4as well as their derivatives 5-7 can be considered as members of the family of 1,1'-binaphthyl-3,3'-diols. The C-1-C'-1 axis of all these compounds was found to have an unusually high rotational barrier. Generally, the

  旋光的（S）-联萘溴化物10与（S）-联萘硼酸11的Suzuki偶联产生了四羟基季萘基4的非对映混合物。偶联产物4及其衍生物5-7可以认为是1,1'-萘基-3,3'-二醇。发现所有这些化合物的C-1-C'-1轴具有异常高的旋转势垒。通常，对于在3和3'位置具有更大的取代基的衍生物，阻挡层更高。
• Reversal of Enantioselectivity Approach to BINOLs via Single and Dual 2-Naphthol Activation Modes
  作者：Hun Young Kim、Shinobu Takizawa、Hiroaki Sasai、Kyungsoo Oh

  DOI：10.1021/acs.orglett.7b01734

  日期：2017.7.21

  A mechanism-driven enantiodivergent approach to chiral 1,1′-bi-2-naphthols via catalytic asymmetric oxidative coupling of 2-naphthol derivatives is described for the first time. By utilizing 2-naphthol derivatives with low oxidation potential, the substrates were activated by either chiral mononuclear or dinuclear vanadium(V) catalyst to promote distinctively different asymmetric reaction pathways:

  首次描述了通过机制驱动的2-萘酚衍生物催化不对称氧化偶联的手性1,1'-bi-2-萘酚的对映异构方法。通过利用具有低氧化电位的2-萘酚衍生物，可以通过手性单核或双核钒（V）催化剂活化底物，从而促进明显不同的不对称反应途径：单底物活化和双底物活化机制。
• Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones
  作者：Kentaro Okuma、Kenta Horigami、Noriyoshi Nagahora、Kosei Shioji

  DOI：10.1055/s-0034-1380452

  日期：——

  The reaction of 2-(trimethylsilyl) phenyl triflate with aroylacetones in the presence of CsF gave the corresponding 4-aryl-2-naphthols. Substituted triflates also reacted with aroylacetones to afford 4-aryl-2-naphthols regioselectively. The enantioselective oxidation of 4aryl-2-naphthols with a chiral tridentate oxovanadium(IV) complex furnished the corresponding 4,4'-biaryl-1,1'-binaphthols in good yields.