2-Benzhydryloxy-2'-hydroxy-1,1'-binaphtyl | 55442-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Benzhydryloxy-2'-hydroxy-1,1'-binaphtyl
• 英文别名: 1-(2-benzhydryloxynaphthalen-1-yl)naphthalen-2-ol
• CAS: 55442-12-1；55515-79-2；1190963-03-1
• 化学式: C₃₃H₂₄O₂
• 分子量: 452.552
• InChiKey: SFJHDWMUAQPOLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Benzhydryloxy-2'-hydroxy-1,1'-binaphtyl 在 三乙胺 、 三氯化磷 作用下， 反应 3.0h， 生成 Tris[1-(2-benzhydryloxynaphthalen-1-yl)naphthalen-2-yl] phosphite
  参考文献：
  名称：

  铑/三-联萘基手性单亚磷酸酯配合物：用于双取代芳基烯烃加氢甲酰化的高效催化剂

  摘要：

  的家庭三重对称亚磷酸酯配体，P（O-BIN-OR）3（BIN = 2,2'-联萘; R = Me中，BN，CHPh配合2，1-金刚烷基），从对映异构纯衍生（[R）-BINOL ， 发展了。使用PM6哈密顿量计算得出亚磷酸酯配体的锥角在240-270°范围内。他们的铑配合物原位形成在相对温和的反应条件下，在受阻苯基丙烯的加氢甲酰化反应中显示出显着的催化活性，对醛具有完全的化学选择性，对区域的选择性高，而对映选择性低。配体上的醚取代基对1，1-和1，2-二取代的芳基烯烃加氢甲酰化反应的催化活性有很大影响。以三[[ R ] -2'-苄氧基-1,1'-联萘-2-基]亚磷酸酯为模型配体，研究了反式-1-苯基-1-丙烯的加氢甲酰化反应动力学。发现加氢甲酰化起始速率相对于底物和催化剂浓度呈一阶依赖性，相对于H 2的分压呈正阶关系。，相对于亚磷酸酯浓度和CO分压，则为负数。

  DOI：

  10.1016/j.jorganchem.2011.10.007
• 作为产物：
  描述：

  二苯甲醇 、 S-1,1'-联-2-萘酚 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 以61%的产率得到2-Benzhydryloxy-2'-hydroxy-1,1'-binaphtyl
  参考文献：
  名称：

  An expedient route to some monoalkyl ethers of enantiomerically pure bi-β-naphthol

  摘要：

  An expedient route to a series of monoalkyl ethers of optically active bi-beta-naphthol has been established by use of the Mitsunobu reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00398-4

文献信息

• Modular chiral polyether podands and their lanthanide complexes
  作者：Helen C Aspinall、Nicholas Greeves、Edward G McIver

  DOI：10.1016/j.tet.2003.06.008

  日期：2003.12

  A novel series of modular chiral polyether podands derived from enantiomerically pure hydrobenzoin and binaphthol has been prepared using a NaH/15-crown-5 mediated Williamson ether synthesis. These new homochiral ligands form catalytically active complexes with lanthanide triflates, two of which have been characterised by X-ray diffraction.

  使用NaH / 15-crown-5介导的Williamson醚合成制备了一系列从对映体纯净的氢安息香和联萘酚衍生的新型模块化手性聚醚荚烷。这些新的同手性配体与镧系元素三氟甲磺酸盐形成催化活性的配合物，其中两个已通过X射线衍射表征。
• Chiral Elaboration of Gold Nanoparticle Surfaces by Bis(binaphthyl) Groups
  作者：Nathan Jones、Mohammad Nuruzzaman、Thomas Preston、Silvia Mittler

  DOI：10.1055/s-2007-1000865

  日期：2008.1

  The synthesis of a family of bis(binaphthyl)-based compounds for the chiral modification of gold nanoparticle surfaces is described. In these systems, two (S)-1,1′-bi-2-naphthol groups are linked to one another by a single diethanolamine-derived bridge, the nitrogen atom of which serves as an anchor for the attachment of an alkanethiol tether of 6, 10, or 12 methylene units in length. The terminal thiol group allows the production of surface-elaborated gold nanoparticles of 2.1 ± 0.6 nm diameter by a ‘direct synthesis’ method.

  描述了一个基于双（苯并萘基）化合物的家族，以实现金纳米颗粒表面的手性改性。在这些体系中，两个（S）-1,1'-双-2-萘醇基团通过一个单一的二乙醇胺衔接，氮原子作为链子与长度为6、10或12个亚甲基单元的烷硫醇连接。终端硫醇基团允许通过“直接合成”方法生产直径为2.1 ± 0.6纳米的表面修饰金纳米颗粒。
• Synthesis of Chiral Bis-MOP-type Diphosphines. Chelating Effect in Nickel-catalyzed Phosphination
  作者：Artur R. Abreu、Andreia F. Peixoto、Ana R. Almeida、Mirtha A. O. Lourenço、Ângela C. B. Neves、J. Carles Bayón、Mariette M. Pereira

  DOI：10.1246/cl.2013.37

  日期：2013.1.5

  Chiral bis-MOP-type diphosphines with alkyl and pyridyl bridges connecting the two binaphthyl units have been synthesized via [NiCl2(dppe)]-assisted phosphination of the corresponding aryl triflates. The effect of the amount of the nickel complex on the reaction yield was investigated. Catalytic and even stoichiometric amounts of the complex proved to be insufficient to promote an efficient phosphination, but the use of an excess of the metal complex provides good yields.

  通过[NiCl2(dppe)]辅助相应芳基三氟酸盐的磷化反应，合成了手性双 MOP 型二磷酸盐，其两个二萘基单元之间有烷基和吡啶基桥连接。研究了镍络合物的数量对反应产率的影响。事实证明，催化量甚至是化学计量量的络合物都不足以促进高效的磷化反应，但使用过量的金属络合物则能提供良好的产率。
• High-Throughput Screening of Enantiomeric Excess (EE)
  申请人：Jones Nathan

  公开号：US20090170213A1

  公开（公告）日：2009-07-02

  The present invention provides a method for high-throughput screening of enantiomeric excess (ee), comprising synthesizing a sensor made from an aggregate of gold nanoparticles whose surfaces have been elaborated with a chiral “host” that includes two optically pure binaphthol groups linked together by a diethanolamine bridge that is tethered via nitrogen to its associated gold nanoparticle, and in which aggregate the individual particles are held together by a bridging chiral “di-guest,” which contains an amino acid functionality at both ends and which interacts with the surface-bound hosts through hydrogen bonds. To screen, one adds a chiral analyte, which may be the product of an asymmetric catalytic reaction, or some other chiral species, in the form of a scalemic solution to a solution containing the aforemeritioned aggregate wherein one enantiomer of the analyte competes effectively with the “di-guest” for the “host,” while the other does not, and wherein a diastereoselective dispersion of the aggregate occurs, which brings about a large shift in the naked-eye-visible plasmon resonance absorption band of the gold nanoparticles, from a long wavelength for the aggregated nanoparticles to a shorter wavelength for the dispersed particles, and wherein the extent of the colour change is indicative of the degree to which the aggregate is dispersed and provides a rapid and effective measure of the ee of the chiral analyte.
• Rhodium/tris-binaphthyl chiral monophosphite complexes: Efficient catalysts for the hydroformylation of disubstituted aryl olefins
  作者：Rui M.B. Carrilho、A.C.B. Neves、Mirtha A.O. Lourenço、Artur R. Abreu、Mário T.S. Rosado、Paulo E. Abreu、M. Ermelinda S. Eusébio、László Kollár、J. Carles Bayón、Mariette M. Pereira

  DOI：10.1016/j.jorganchem.2011.10.007

  日期：2012.2

  considerably the catalytic activity on the hydroformylation of 1,1- and 1,2-disubstituted aryl olefins. The kinetics of the hydroformylation of trans-1-phenyl-1-propene, using tris[(R)-2′-benzyloxy-1,1′-binaphthyl-2-yl]phosphite as model ligand, was investigated. A first order dependence in the hydroformylation initial rate with respect to substrate and catalyst concentrations was found, as well as a positive

  的家庭三重对称亚磷酸酯配体，P（O-BIN-OR）3（BIN = 2,2'-联萘; R = Me中，BN，CHPh配合2，1-金刚烷基），从对映异构纯衍生（[R）-BINOL ， 发展了。使用PM6哈密顿量计算得出亚磷酸酯配体的锥角在240-270°范围内。他们的铑配合物原位形成在相对温和的反应条件下，在受阻苯基丙烯的加氢甲酰化反应中显示出显着的催化活性，对醛具有完全的化学选择性，对区域的选择性高，而对映选择性低。配体上的醚取代基对1，1-和1，2-二取代的芳基烯烃加氢甲酰化反应的催化活性有很大影响。以三[[ R ] -2'-苄氧基-1,1'-联萘-2-基]亚磷酸酯为模型配体，研究了反式-1-苯基-1-丙烯的加氢甲酰化反应动力学。发现加氢甲酰化起始速率相对于底物和催化剂浓度呈一阶依赖性，相对于H 2的分压呈正阶关系。，相对于亚磷酸酯浓度和CO分压，则为负数。