(S)-(2-nitrophenyl)(phenyl)methanol

• 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: (S)-(2-nitrophenyl)(phenyl)methanol
• 英文别名: (S)-(2-nitrophenyl)-phenylmethanol
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: AIHHQWUKHCUKLJ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2-硝基苯基)苯基-甲酮 在 C₃₂H₃₉BrMnN₂O₂P 、 potassium tert-butylate 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 反应 16.0h， 以99%的产率得到(S)-(2-nitrophenyl)(phenyl)methanol
  参考文献：
  名称：

  基于卢替丁的手性钳式锰催化剂，用于酮的对映选择性加氢

  摘要：

  已经开发了一系列含有基于核苷的手性钳式配体的Mn I配合物，这些配合物具有模块化和可调的结构。该配合物在各种酮的氢化反应中显示出前所未有的高活性（高达9800 TON； TON =周转数），广泛的底物范围（81个实例），良好的官能团耐受性和出色的对映选择性（85-98％ee）。这些方面在稀土金属催化的氢化反应中很少见。该协议的实用性已在手性药物的多种关键中间体的不对称合成中得到证明。初步的机理研究表明，底物与催化剂相互作用的外层模式可能主导了催化作用。

  DOI：

  10.1002/anie.201814751

文献信息

• 手性氨基-吡啶-膦三齿配体、锰络合物、其制备方法和应用
  申请人：中国科学院上海有机化学研究所

  公开号：CN111320651B

  公开（公告）日：2023-01-17

  本发明公开了一种手性氨基‑吡啶‑膦三齿配体、锰络合物、其制备方法和应用。本发明手性氨基‑吡啶‑膦三齿配体如式II所示，该手性氨基‑吡啶‑膦三齿配体的锰络合物可用于高效、高对映选择性地催化氢化酮类化合物制备手性醇类化合物。本发明的手性氨基‑吡啶‑膦三齿配体和锰络合物合成工艺简单，稳定性好，催化活性高，反应条件温和。
• Enantioselective Rhodium-Catalyzed Addition of Arylboronic Acids to Aldehydes Using Chiral Spiro Monophosphite Ligands
  作者：Hai-Feng Duan、Jian-Hua Xie、Wen-Jian Shi、Qi Zhang、Qi-Lin Zhou

  DOI：10.1021/ol060360c

  日期：2006.3.1

  [reaction: see text] Highly efficient rhodium-catalyzed asymmetric addition of arylboronic acids to aldehydes has been realized by using chiral spiro monophosphite ligands, affording diarylmethanols in excellent yields and good enantiomeric excesses.

  [反应：见正文]通过使用手性螺一亚磷酸酯配体实现了铑催化芳基硼酸向醛的高效不对称加成，从而以优异的收率和良好的对映体过量提供了二芳基甲醇。
• 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。
• Validation of PqsD as an Anti-biofilm Target in Pseudomonas aeruginosa by Development of Small-Molecule Inhibitors
  作者：Michael P. Storz、Christine K. Maurer、Christina Zimmer、Nathalie Wagner、Christian Brengel、Johannes C. de Jong、Simon Lucas、Mathias Müsken、Susanne Häussler、Anke Steinbach、Rolf W. Hartmann

  DOI：10.1021/ja3072397

  日期：2012.10.3

  2-Hepty1-4-hydroxyquinoline (HHQ) and Pseudomonas quinolone signal (PQS) are involved in the regulation of virulence factor production and biofilm formation in Pseudomonas aeruginosa. PqsD is a key enzyme in the biosynthesis of these signal molecules. Using a ligand-based approach, we have identified the first class of PqsD inhibitors. Simplification and rigidization led to fragments with high ligand efficiencies. These small molecules repress HHQ and PQS production and biofilm formation in P. aeruginosa. This validates PqsD as a target for the development of anti-infectives.
• A chiral Rh–phosphite complex displaying high activity in the enantioselective Rh-catalyzed addition of arylboronic acids to carbonyl compounds: when and why atropos is better than tropos
  作者：Varsha R. Jumde、Sarah Facchetti、Anna Iuliano

  DOI：10.1016/j.tetasy.2010.11.009

  日期：2010.12

  The use of deoxycholic acid derived tropos and atropoisomeric phosphites as chiral ligands in the Rh-catalyzed enantioselective addition of arylboronic acids to arylaldehydes and 2,2,2-trifluoroacetophenone is presented. Screening of these phosphites showed the high activity of the Rh-complex obtained starting from one of the two atropoisomeric ligands, which afforded complete conversion of the carbonyl compounds in short reaction times under mild reaction conditions and with ee's of up to 84%. A study aimed at getting information about the different behavior of tropos and atropoisomeric ligands is also reported. (C) 2010 Elsevier Ltd. All rights reserved.