(-)-2-(3-methoxyphenylamino)cyclohexanol | 1262120-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (-)-2-(3-methoxyphenylamino)cyclohexanol
• 英文别名: (1R,2R)-2-(3-methoxyanilino)cyclohexan-1-ol
• CAS: 1262120-96-6
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: OVTBENIXXOONJI-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  间氨基苯甲醚 、 氧化环己烯 在 zirconyl triflate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以84%的产率得到(-)-2-(3-methoxyphenylamino)cyclohexanol
  参考文献：
  名称：

  Highly Efficient Aminolysis of Epoxides Catalyzed by Reusable Zirconyl Triflate, ZrO(OTf)₂

  摘要：

  Efficient ring opening of epoxides with aromatic amines catalyzed by ZrO(OTf)(2) is reported, and the corresponding beta amino (beta-amino acid) alcohols were obtained in high yields in CH3CN as solvent. The reactions were carried out at room temperature and in the presence of only 1.25 mol% of ZrO(OTf)(2). This catalyst can be reused several times without loss of its activity.

  DOI：

  10.1080/00397910802406729

文献信息

• Enantioselective Ring Opening of<i>meso</i>-Epoxides with Aromatic Amines Catalyzed by Dinuclear Magnesium Complexes
  作者：Hongli Bao、Zheng Wang、Tianpa You、Kuiling Ding

  DOI：10.1002/cjoc.201201008

  日期：2013.1

  The dinuclear magnesium complexes generated in situ from the reaction of chiral multidentate semi‐azacrown ether ligands with n‐Bu2Mg were found to be efficient catalysts for enantioselective ring‐opening of meso‐epoxides with aniline derivatives, affording the corresponding chiral β‐amino alcohols in good yields with up to 90% ee.

  已发现手性多齿半氮杂半氮杂醚配体与n- Bu 2 Mg反应原位生成的双核镁配合物是介孔环氧化物与苯胺衍生物对映选择性开环的有效催化剂，提供了相应的手性β-氨基醇，产率高，ee高达90％。
• Enantioselective Ring Opening Reaction of meso-Epoxides with Aromatic and Aliphatic Amines Catalyzed by Magnesium Complexes of BINOL Derivatives
  作者：Hongli Bao、Jiang Wu、Hongji Li、Zheng Wang、Tianpa You、Kuiling Ding

  DOI：10.1002/ejoc.201001222

  日期：2010.12

  Catalyzed by the Mg complexes of BINOL derivatives, the enantioselective ring opening reaction of various meso-epoxides proceeded smoothly with either aromatic or aliphatic amines as the nucleophiles to afford the corresponding chiral β-amino alcohols in moderate-to-high yields with good to excellent enantioselectivities.

  在 BINOL 衍生物的镁配合物催化下，各种内消旋环氧化物的对映选择性开环反应以芳香族或脂肪族胺作为亲核试剂顺利进行，以中等至高产率获得相应的手性 β-氨基醇对映选择性。
• Turning on Asymmetric Catalysis of Achiral Metal‐Organic Frameworks by Imparting Chiral Microenvironment
  作者：Ge Yang、Wenwen Shi、Yunyang Qian、Xiao Zheng、Zheng Meng、Hai‐Long Jiang

  DOI：10.1002/anie.202308089

  日期：2023.9.18

  The chiral microenvironment around catalytically active metal clusters in a MOF, PCN-222(Cu), is created by simply grafting chiral molecules (R)−Cn−COOH (n=1, 2, 3). Owing to multi-level modulation such as hydrogen interaction, steric hindrance, and confinement effect caused by the microenvironment, the resulting (R)−Cn@PCN-222(Cu) exhibits high activity and enantioselectivity in the asymmetric ring-opening

  MOF PCN-222(Cu) 中催化活性金属簇周围的手性微环境是通过简单地接枝手性分子 ( R )−C n −COOH ( n =1, 2, 3) 来创建的。由于微环境引起的氢相互作用、空间位阻和限域效应等多级调节，所得的( R )−C n @PCN-222(Cu)在环己烯的不对称开环中表现出高活性和对映选择性与苯胺氧化。