(1R,2R)-2-(4-chlorophenylamino)-1,2-diphenylethanol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1R,2R)-2-(4-chlorophenylamino)-1,2-diphenylethanol
• 英文别名: (1R,2R)-2-(4-chloroanilino)-1,2-diphenylethanol
• 化学式: C₂₀H₁₈ClNO
• 分子量: 323.822
• InChiKey: OFGJRGQBDDSFSC-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯苯胺 在 lithium aluminium tetrahydride 、 1-phenyl-ethylamine 作用下， 以 乙醚 、 xylene 为溶剂， 反应 9.0h， 生成 (1R,2R)-2-(4-chlorophenylamino)-1,2-diphenylethanol
  参考文献：
  名称：

  Alcaide, Benito; Lopez-Mardomingo, Carmen; Perez-Ossorio, Rafael, Journal of the Chemical Society. Perkin transactions II, 1983, # 11, p. 1649 - 1654

  摘要：

  DOI：

文献信息

• Indium-Bipyridine Catalyzed, Enantioselective Aminolysis of <i>meso</i>-Epoxides
  作者：Christoph Schneider、Enzo Mai

  DOI：10.1055/s-2007-984902

  日期：——

  The scandium-bipyridine-catalyzed enantioselective addition of anilines and O-alkyl hydroxylamines to meso-epoxides has been optimized and extended to a broad range of epoxides and amines. Whereas aromatic meso-epoxides generally furnished the corresponding 1,2-amino alcohols in excellent enantioselectivities, aliphatic meso-epoxides only gave rise to moderate enantioselectivities in the aminolysis

  钪-联吡啶催化的苯胺和 O-烷基羟胺对内消旋环氧化物的对映选择性加成已被优化并扩展到范围广泛的环氧化物和胺。芳香族内消旋环氧化物通常以优异的对映选择性提供相应的 1,2-氨基醇，而脂肪族内消旋环氧化物仅在氨解中产生中等的对映选择性。催化剂负载量可降低至仅 5 mol%，而对产率和对映选择性的影响很小。已经观察到强烈的正非线性效应，表明催化剂的聚集现象。
• Asymmetric Ring Opening ofmeso-Epoxides with Aromatic Amines Catalyzed by a New Proline-BasedN,N′-Dioxide-Indium Tris(triflate) Complex
  作者：Bo Gao、Yuehong Wen、Zhigang Yang、Xiao Huang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/adsc.200700474

  日期：2008.2.22

  The catalytic asymmetric ring opening of meso-epoxides with aromatic amines was achieved using a new proline-based N,N′-dioxide-indium tris(triflate) complex in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee) under mild conditions. The coordination ability of N,N′-dioxide 1c was investigated by X-ray and NMR analysis. A plausible seven-coordinate transition state model was

  的不对称催化开环内消旋与芳族胺-环氧化物用新的基于脯氨酸达到Ñ，N'二氧化物-铟三（三氟甲磺酸酯）配合物以高产率（高达99％）的对映选择性优良（高达99％ee）在温和的条件下。通过X射线和NMR分析研究N，N'-二氧化物1c的配位能力。提出了一个合理的七坐标过渡状态模型。手性N，N'仅通过三个常规步骤，由脯氨酸合成了所调查的二氧化di。该过程可以在克规模上运行而不会损失任何对映选择性。该方案为大量制备光学纯的β-氨基醇提供了高度实用和有用的工具。
• Scandium–Bipyridine-Catalyzed Enantioselective Aminolysis ofmeso-Epoxides
  作者：Enzo Mai、Christoph Schneider

  DOI：10.1002/chem.200601307

  日期：2007.3.16

  The scandium-bipyridine-catalyzed enantioselective addition of anilines and O-alkyl hydroxylamines to meso-epoxides has been optimized and extended to a broad range of epoxides and amines. Whereas aromatic meso-epoxides generally furnished the corresponding 1,2-amino alcohols in excellent enantioselectivities, aliphatic meso-epoxides only gave rise to moderate enantioselectivities in the aminolysis

  optimized联吡啶催化苯胺和O-烷基羟胺对映体环氧化物的对映选择性加成已得到优化，并扩展到广泛的环氧化物和胺中。芳族内消旋环氧化物通常以优异的对映选择性提供相应的1,2-氨基醇，而脂族内消旋环氧化物仅在氨解反应中产生中等对映选择性。催化剂的加入量可以降低到仅5mol％，而对收率和对映选择性只有很小的影响。已经观察到强烈的正非线性效应，指出了催化剂的聚集现象。
• Thieme Chemistry Journal Awardees - Where Are They Now? Bifunctional Organocatalysis with N-Formyl-l-Proline: A Novel Approach to Epoxide Ring Opening and Sulfide Oxidation
  作者：Svetlana Tsogoeva、Shengwei Wei、Kerstin Stingl、Katharina Weiß

  DOI：10.1055/s-0029-1219363

  日期：2010.3

  A conceptually distinct approach to the aminolysis of 1,2-epoxides, which involves Lewis base-Brønsted acid catalysis employing N-formyl-l-proline as an easily accessible bifunctional organocatalyst and water as a solvent is presented. The potential of N-formyl-l-proline as organocatalyst for the sulfide oxidation reaction using aqueous hydrogen peroxide as environmentally benign and readily available oxidant is also demonstrated. Good to high yields are achieved for both reactions.

  提出了一种概念上截然不同的方法来实现1,2-环氧化物的氨基解反应，该方法采用易于获得的N-甲酰基-L-脯氨酸作为双功能有机催化剂，通过路易斯碱-布朗斯特酸催化，并以水为溶剂。同时，也展示了N-甲酰基-L-脯氨酸作为有机催化剂在硫化物氧化反应中的潜力，使用环保且易于获得的过氧化氢水溶液作为氧化剂。这两种反应均获得了良好至高产率的结果。
• Highly Enantioselective Ring‐Opening of <i>meso‐</i> Epoxides with O‐ and <i>N‐</i> Nucleophiles Catalyzed by a Chiral Sc(III)/bipyridine Complex
  作者：Štefan Malatinec、Eva Bednářová、Hiroki Tanaka、Martin Kotora

  DOI：10.1002/ejoc.202001493

  日期：2021.2.25

  A newly designed ligand with the bipyridine scaffold (an analog of Bolm's ligand), in combination with Sc(OTf)3, exhibits high stereocontrol in the ring opening of meso‐epoxides with various alcohols providing 1,2‐alkoxyalcohols.

  新设计的配体与联吡啶骨架（Bolm的配体的类似物），结合钪（OTF）3，表现出的开环高立体控制的内消旋环氧化物与各种醇提供1,2-烷氧基醇。