(2R,3S)-3-(2-methoxyphenylamino)butan-2-ol | 1231757-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3S)-3-(2-methoxyphenylamino)butan-2-ol
• 英文别名: (2S,3R)-3-(2-methoxyanilino)butan-2-ol
• CAS: 1231757-97-3
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: HPBNNPABPOHKBI-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲氧基苯胺 、 2,3-trans-epoxybutane 在 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino chromium(III) chloride 作用下， 反应 18.0h， 以80%的产率得到(2R,3S)-3-(2-methoxyphenylamino)butan-2-ol
  参考文献：
  名称：

  Aminolytic kinetic resolution of trans epoxides for the simultaneous production of chiral trans β-amino alcohols in the presence of chiral Cr(III) salen complex using an ionic liquid as a green reaction media

  摘要：

  Chiral Cr(III) salen complex 1 having t-Bu substituents at 3,3' and 5,5'-positions was used as a catalyst for the highly enantioselective aminolytic kinetic resolution (AKR) of racemic trans epoxides with different anilines as nucleophile in the presence of different ionic liquids at rt. Excellent yields (>98%) of anti beta-aminoalcohols with high enantioselectivity (ee >99%) was achieved in 4 h when [bmim]PF6 was used as the ionic liquid. The present ionic liquid mediated AKR process is recyclable (up to six cycles with no loss in performance) and is five times quicker than the homogeneous process utilizing conventional organic solvents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.021

文献信息

• Reusable Chiral Dicationic Chromium(III) Salen Catalysts for Aminolytic Kinetic Resolution of trans-Epoxides
  作者：Rukhsana I. Kureshy、K. Jeya Prathap、Tamal Roy、Nabin Ch. Maity、Noor-ul H. Khan、Sayed H. R. Abdi、Hari C. Bajaj

  DOI：10.1002/adsc.201000428

  日期：2010.11.22

  These complexes were used as catalysts for the highly enantioselective aminolytic kinetic resolution of racemic trans-epoxides with different anilines as nucleophiles at room temperature. With the use of catalyst 3, anti-β-amino alcohols were obtained in excellent yields (>99% with respect to the nucleophile) and enantioselectivities (ee>99%) with the concomitant recovery of corresponding epoxides in

  A series of new recyclable chiral dicationic chromium(III) salen complexes 1–10 bearing different substituents, viz., hydrogen, methyl, tert-butyl, triphenylphosphinomethyl, triethylaminomethyl, methylimidazolium, methylpyridinium, methyl-N,N-dimethylpyridinium at the 3,3′- and 5,5′- positions of the salen unit with (1S,2S)-(+)-1,2-diaminocyclohexane, (1S,2S)-(−)-1,2-diphenyl-1,2-diaminoethane, and
• Aminolytic kinetic resolution of trans epoxides for the simultaneous production of chiral trans β-amino alcohols in the presence of chiral Cr(III) salen complex using an ionic liquid as a green reaction media
  作者：Rukhsana I. Kureshy、Manish Kumar、Santosh Agrawal、Noor-ul H. Khan、Sayed H.R. Abdi、Hari C. Bajaj

  DOI：10.1016/j.tetasy.2010.02.021

  日期：2010.3

  Chiral Cr(III) salen complex 1 having t-Bu substituents at 3,3' and 5,5'-positions was used as a catalyst for the highly enantioselective aminolytic kinetic resolution (AKR) of racemic trans epoxides with different anilines as nucleophile in the presence of different ionic liquids at rt. Excellent yields (>98%) of anti beta-aminoalcohols with high enantioselectivity (ee >99%) was achieved in 4 h when [bmim]PF6 was used as the ionic liquid. The present ionic liquid mediated AKR process is recyclable (up to six cycles with no loss in performance) and is five times quicker than the homogeneous process utilizing conventional organic solvents. (C) 2010 Elsevier Ltd. All rights reserved.