(R)-(3,5-二甲基苯基)(苯基)甲醇 | 807632-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-(3,5-二甲基苯基)(苯基)甲醇
• 英文名称: (R)-(3,5-dimethylphenyl)-phenylmethanol
• CAS: 807632-31-1
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: SLNXZUABMKSUBT-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,5-dimethylphenyl-2-dimethylphenylsilylphenylmethanol 在 cesium fluoride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以100%的产率得到(R)-(3,5-二甲基苯基)(苯基)甲醇
  参考文献：
  名称：

  Et-duphos-nickel-catalyzed asymmetric arylation of benzaldehyde derivatives bearing an ortho-Me2PhSi group with potassium aryltriolborates

  摘要：

  The Ni-catalyzed asymmetric arylation of benzaldehydes bearing an ortho-masked H group with potassium aryltriolborates has been developed. The keys to success were (i) steric tuning of benzaldehyde derivatives with an ortho-Me2PhSi group, and (ii) the use of potassium aryltriolborates as aryl sources. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.019

文献信息

• Catalytic Enantioselective Aryl Transfer to Aldehydes Using Chiral 2,2’-Bispyrrolidine-Based Salan Ligands
  作者：Xuefeng Jia、Aijun Lin、Zhijie Mao、Chengjian Zhu、Yixiang Cheng

  DOI：10.3390/molecules16042971

  日期：——

  Chiral C₂-symmetric diamines have emerged as versatile auxiliaries or ligands in numerous asymmetric transformations. Chiral 2,2'-bispyrrolidine-based salan ligands were prepared and applied to the asymmetric aryl transfer to aldehydes with arylboronic acids as the source of transferable aryl groups. The corresponding diarylmethanols were obtained in high yields with moderate to good enantioselectivitives

  手性 C 2 对称二胺已成为众多不对称转化中的通用助剂或配体。制备了基于手性 2,2'-双吡咯烷的 Salan 配体，并将其应用于以芳基硼酸作为可转移芳基来源的醛的不对称芳基转移。相应的二芳基甲醇以高产率获得，对映选择性高达 83% ee。
• Design and Synthesis of Tunable Chiral 2,2′‐Bipyridine Ligands: Application to the Enantioselective Nickel‐Catalyzed Reductive Arylation of Aldehydes
  作者：Shuai Zhang、Saima Perveen、Yizhao Ouyang、Liang Xu、Tao Yu、Min Zhao、Linghua Wang、Peidong Song、Pengfei Li

  DOI：10.1002/anie.202117843

  日期：2022.5.9

  A tunable chiral 2,2′-bipyridine scaffold SBpy was rationally designed and enabled a general and highly enantioselective Ni-catalyzed addition of aryl halides to aldehydes. This approach is more step-economic than conventional strategies and allowed the preparation of various diaryl carbinols without the need to use preformed metallic reagents.

  合理设计了一种可调节的手性 2,2'-联吡啶支架 SBpy，并能够在 Ni 催化下将芳基卤化物与醛类进行通用且高度对映选择性的加成。这种方法比传统策略更经济，并且无需使用预制金属试剂即可制备各种二芳基甲醇。
• Enantioselective Reduction of Diaryl Ketones Catalyzed by a Carbonyl Reductase from<i>Sporobolomyces salmonicolor</i>and its Mutant Enzymes
  作者：Hongmei Li、Dunming Zhu、Ling Hua、Edward R. Biehl

  DOI：10.1002/adsc.200900045

  日期：2009.3

  Abstractmagnified imageThe carbonyl reductase from red yeast Sporobolomyces salmonicolor AKU4429 (SSCR) and its mutant enzymes effectively catalyzed the enantioselective reduction of diaryl ketones to give the corresponding chiral alcohols. Both conversion and enantioselectivity were dependent on the co‐solvent in the reaction medium. Diaryl ketones with a para‐substituent on one of the phenyl groups were reduced with high enantioselectivity (up to 99% ee), which is difficult to achieve using chemical methods such as chiral borane reduction, asymmetric hydrogenation or hydrosilylation. Mutation of SSCR at Q245 resulted in a higher amount of (S)‐enantiomer in the products, and in the case of mutant Q245P with para‐substituted diaryl ketones as substrate, this effect was so remarkable that the reduction enantiopreference was switched from (R) to (S). The present study provides valuable information about the catalytic properties of the carbonyl reductase SSCR toward the reduction of diaryl ketones, serving as basis for further engineering of this enzyme to develop efficient biocatalysts for highly enantiospecific reduction of diaryl ketones without high electronic dissymmetry or an ortho‐substituent on one of the aryl groups.
• Et-duphos-nickel-catalyzed asymmetric arylation of benzaldehyde derivatives bearing an ortho-Me2PhSi group with potassium aryltriolborates
  作者：Fumie Sakurai、Kazuhiro Kondo、Toyohiko Aoyama

  DOI：10.1016/j.tetlet.2009.08.019

  日期：2009.11

  The Ni-catalyzed asymmetric arylation of benzaldehydes bearing an ortho-masked H group with potassium aryltriolborates has been developed. The keys to success were (i) steric tuning of benzaldehyde derivatives with an ortho-Me2PhSi group, and (ii) the use of potassium aryltriolborates as aryl sources. (C) 2009 Elsevier Ltd. All rights reserved.