3,8-diphenylnaphthalen-1-ol | 1187096-56-5

• 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: 3,8-diphenylnaphthalen-1-ol
• 英文别名: 3,8-Diphenylnaphthalen-1-ol
• CAS: 1187096-56-5
• 化学式: C₂₂H₁₆O
• 分子量: 296.368
• InChiKey: KFHBXTYELNPUQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,8-diphenylnaphthalen-1-ol 在 air 作用下， 反应 60.0h， 以54%的产率得到(S)-3,3',8,8'-tetraphenyl-2,2'-binaphthyl-1,1'-diol
  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：

  3,8-diphenylnaphthalen-1-yl acetate 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 以94%的产率得到3,8-diphenylnaphthalen-1-ol
  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

文献信息

• 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