(S)-3,3',8,8'-tetraphenyl-2,2'-binaphthyl-1,1'-diol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (S)-3,3',8,8'-tetraphenyl-2,2'-binaphthyl-1,1'-diol
• 英文别名: (aS)-8,8'-Ph2VANOL；(S)-8,8'-Ph2 VANOL；2-(1-Hydroxy-3,8-diphenylnaphthalen-2-yl)-3,8-diphenylnaphthalen-1-ol；2-(1-hydroxy-3,8-diphenylnaphthalen-2-yl)-3,8-diphenylnaphthalen-1-ol
• 化学式: C₄₄H₃₀O₂
• 分子量: 590.721
• InChiKey: ZXZSZKZWNCRHTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  8.0
• 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：

  (S)-3,3',8,8'-tetraphenyl-2,2'-binaphthyl-1,1'-diol 在 吡啶 、 三氯氧磷 作用下， 反应 24.0h， 以56%的产率得到(S)-8,8'-Ph2 VANOL phosphorus oxychloride
  参考文献：
  名称：

  VAPOL和VANOL的新衍生物：结构不同的拱形手性配体和布朗斯台德酸催化剂

  摘要：

  描述了许多新的VAPOL和VANOL衍生物的精简和有效的克级合成。这些是结构上新颖的手性配体和布朗斯台德酸催化剂，可以为催化中的反应性和不对称诱导提供奇异的分布。 VAPOL-VANOL-配体-布朗斯台德酸-不对称催化

  DOI：

  10.1055/s-0030-1258231
• 作为产物：
  描述：

  在 溶剂黄146 、 锌 作用下， 反应 36.0h， 以57%的产率得到(S)-3,3',8,8'-tetraphenyl-2,2'-binaphthyl-1,1'-diol
  参考文献：
  名称：

  Optically Active (aR)- and (aS)-Linear and Vaulted Biaryl Ligands: Deracemization versus Oxidative Dimerization

  摘要：

  The copper-mediated deracemization of the C2-symmetric vaulted biaryl ligands VANOL and VAPOL has been investigated. In the course of the studies that have led to a more reliable procedure for this process, an unprecedented oxidative dimerization of these ligands has been uncovered. The structures of these oxidative dimerization products were elucidated by a series of NMR experiments, and these assignments were supported by other spectroscopic techniques as well as their chemical reactivity. This oxidative dimerization process was not observed for the linear biaryl ligands BANOL and BINOL, although the new deracemization procedure was effective for the generation of BINOL with high optical purity. The (aS)-enantiomers of BINOL, VANOL and VAPOL were accessible with a copper complex of (-)-sparteine, and the (aR)-enantiomeric series were accessible with a copper complex of O'Brien's diamine. Both sparteine and O'Brien's diamine give higher optical purities with VANOL and VAPOL than with BINOL, and this is consistent with the steric congestion present in the matched and mismatched copper complexes of these diamines with the biaryl ligands.

  DOI：

  10.1021/ja903820m

文献信息

• 2,2'-Binaphthalene Ester Chiral Dopants for Cholesteric Liquid Crystal Displays
  申请人：Diehl Donald R.

  公开号：US20140054498A1

  公开（公告）日：2014-02-27

  A liquid crystal composition comprising a chiral dopant compound represented by the following structure (Structure 1): wherein: R1 and R2 are independently hydrogen, —(C═O)R9, —(C═O)R10, alkyl, aryl, alkaryl, alkenyl, cycloalkyl, alkoxyaryl, or heterocyclic all either substituted or unsubstituted, or combine to form a carbocyclic or heterocyclic ring; and R3-R9 are as described in the disclosure. Also featured are liquid crystal compositions comprising a chiral dopant compound represented by any of Structure 2-4 as described in the disclosure.

  一种液晶组合物，包括由以下结构（结构1）表示的手性掺杂剂化合物：其中：R1和R2独立地是氢，—(C═O)R9，—(C═O)R10，烷基，芳基，烷芳基，烯基，环烷基，烷氧基芳基，或杂环烷基，均为取代或未取代，或结合形成碳环或杂环；R3-R9如披露中所述。还包括由披露中描述的结构2-4中的任何一个表示的手性掺杂剂化合物的液晶组合物。
• US8709281B2
  申请人：——

  公开号：US8709281B2

  公开（公告）日：2014-04-29
• US9005478B2
  申请人：——

  公开号：US9005478B2

  公开（公告）日：2015-04-14
• Optically Active (<i>aR</i>)- and (<i>aS</i>)-Linear and Vaulted Biaryl Ligands: Deracemization versus Oxidative Dimerization
  作者：Gang Hu、Daniel Holmes、Brina Fay Gendhar、William D. Wulff

  DOI：10.1021/ja903820m

  日期：2009.10.14

  The copper-mediated deracemization of the C2-symmetric vaulted biaryl ligands VANOL and VAPOL has been investigated. In the course of the studies that have led to a more reliable procedure for this process, an unprecedented oxidative dimerization of these ligands has been uncovered. The structures of these oxidative dimerization products were elucidated by a series of NMR experiments, and these assignments were supported by other spectroscopic techniques as well as their chemical reactivity. This oxidative dimerization process was not observed for the linear biaryl ligands BANOL and BINOL, although the new deracemization procedure was effective for the generation of BINOL with high optical purity. The (aS)-enantiomers of BINOL, VANOL and VAPOL were accessible with a copper complex of (-)-sparteine, and the (aR)-enantiomeric series were accessible with a copper complex of O'Brien's diamine. Both sparteine and O'Brien's diamine give higher optical purities with VANOL and VAPOL than with BINOL, and this is consistent with the steric congestion present in the matched and mismatched copper complexes of these diamines with the biaryl ligands.
• New Derivatives of VAPOL and VANOL: Structurally Distinct Vaulted Chiral Ligands and Brønsted Acid Catalysts
  作者：William Wulff、Aman Desai

  DOI：10.1055/s-0030-1258231

  日期：2010.11

  Lean and efficient multi-gram scale syntheses of a number of new derivatives of VAPOL and VANOL are described. These are structurally novel chiral ligands and Brønsted acid catalysts, and could provide singular profiles for reactivity and asymmetric inductions in catalysis. VAPOL - VANOL - ligand - Brønsted acid - asymmetric catalysis

  描述了许多新的VAPOL和VANOL衍生物的精简和有效的克级合成。这些是结构上新颖的手性配体和布朗斯台德酸催化剂，可以为催化中的反应性和不对称诱导提供奇异的分布。 VAPOL-VANOL-配体-布朗斯台德酸-不对称催化