(2R,3S)-3-(phenylamino)butan-2-ol | 1342297-64-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,3S)-3-(phenylamino)butan-2-ol
• 英文别名: (1R,2R)-3-(phenylamino)-2-butanol；(2R,3S)-3-anilinobutan-2-ol
• CAS: 1342297-64-6
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: XTYMSXNQWSWSOU-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三光气 、 (2R,3S)-3-(phenylamino)butan-2-ol 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 以86%的产率得到(4S,5R)-4,5-dimethyl-3-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α-Branched Amines

  摘要：

  The first dynamic kinetic asymmetric amination of alcohols via borrowing hydrogen methodology is presented. Under the cooperative catalysis by an iridium complex and a chiral phosphoric acid, a-branched alcohols that exist as a mixture of four isomers undergo racemization by two orthogonal mechanisms and are converted to diastereo- and enantiopure amines bearing adjacent stereocenters. The preparation of diastereo- and enantiopure 1,2-amino alcohols is also realized using this catalytic system.

  DOI：

  10.1021/jacs.5b02212
• 作为产物：
  描述：

  N-((2S,3R)-3-(tert-butyldimethylsilyloxy)butan-2-yl)aniline 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (2R,3S)-3-(phenylamino)butan-2-ol
  参考文献：
  名称：

  Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α-Branched Amines

  摘要：

  The first dynamic kinetic asymmetric amination of alcohols via borrowing hydrogen methodology is presented. Under the cooperative catalysis by an iridium complex and a chiral phosphoric acid, a-branched alcohols that exist as a mixture of four isomers undergo racemization by two orthogonal mechanisms and are converted to diastereo- and enantiopure amines bearing adjacent stereocenters. The preparation of diastereo- and enantiopure 1,2-amino alcohols is also realized using this catalytic system.

  DOI：

  10.1021/jacs.5b02212

文献信息

• Chiral zinc(II) and copper(II)-catalyzed asymmetric ring-opening reactions of meso-epoxides with aniline and indole derivatives
  作者：Masaya Kokubo、Takeshi Naito、Shū Kobayashi

  DOI：10.1016/j.tet.2009.11.018

  日期：2010.1

  The ring-opening reactions of meso-epoxides with aniline and indole derivatives proceeded smoothly in water in the presence of Zn(II) and Cu(II) surfactant-type catalysts to afford the corresponding products in moderate to high yields with good to excellent enantioselectivities. Opposite enantiomers were obtained by using Sc(III) and Zn(II) or Cu(II) with the same chiral ligand. Crystal structures

  的开环反应的内消旋环氧化物与苯胺和吲哚衍生物在水顺利进行中的Zn（II）和Cu的存在下（Ⅱ）表面活性剂类催化剂，得到相应的产品在中度到高收率和良好至优异的对映选择性。相反的对映体是通过使用具有相同手性配体的Sc（III）和Zn（II）或Cu（II）获得的。这些催化剂的晶体结构可以解释对映选择性的逆转。还在二氯甲烷（DCM）中测试了一些反应，结果表明，在水中的反应比在DCM中进行的更快。最后，一些非线性效应实验表明这些手性催化剂具有独特的结构。
• Catalytic enantioselective Amadori–Heyns rearrangement of racemic α-hydroxy ketones with arylamines: synthesis of optically active α-arylamino ketones
  作者：Angelo Frongia、Francesco Secci、Francesca Capitta、Pier Paolo Piras、Maria Luisa Sanna

  DOI：10.1039/c3cc45278f

  日期：——

  A novel synthesis of optically active alpha-arylamino ketones through an organocatalytic enantioselective Amadori-Heyns rearrangement is described.

  描述了一种通过有机催化对映选择性Amadori-Heyns重排的新型光学活性α-芳基氨基酮的合成方法。
• Development of recyclable chiral macrocyclic metal complexes for asymmetric aminolysis of epoxides: application for the synthesis of an enantiopure oxazolidine ring
  作者：Raj Kumar Tak、Manish Kumar、Mohd Nazish、Tushar Kumar Menapara、Rukhsana I. Kureshy、Noor-ul H. Khan

  DOI：10.1039/c8nj02960a

  日期：——

  New recyclable chiral salen complexes Cr(III)1–7 were synthesized from various macrocyclic chiral ligands having multistereogenic chiral centers which work synergistically to give the best results in terms of the enantioselectivity and yield of the products. Among the synthesized complexes, the Cr(III)-4 salen complex efficiently catalyzed the ring opening reaction of various aromatic ester epoxides

  由具有大立体手性中心的各种大环手性配体合成了新的可回收的手性salen配合物Cr（III）1-7，它们在对映选择性和产物收率方面具有协同作用，从而获得最佳结果。在合成的配合物中，Cr（III）-4 salen配合物有效地催化了各种芳族​​酯环氧化物，反式环氧化物和内消旋体的开环反应。-与苯胺形成的环氧化物提供相应的β-氨基-α-羟基酯和β-氨基醇，其ee高达99％，收率高达95％。此外，手性纯的β-氨基-α-羟基酯被转化成药学上重要的恶唑烷环系统。此外，铬催化剂可循环使用多达5个循环，并保持其活性。
• Xie, Jian-Hua; Liu, Sheng; Kong, Wei-Ling, Journal of the American Chemical Society, 2009, vol. 131, p. 4222 - 4223
  作者：Xie, Jian-Hua、Liu, Sheng、Kong, Wei-Ling、Bai, Wen-Ju、Wang, Xiao-Chen、et al.

  DOI：——

  日期：——