2-(4-chlorophenylamino)cyclohexanol | 210408-09-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4-chlorophenylamino)cyclohexanol
• 英文别名: (1R,2R)-2-(4-chloroanilino)cyclohexan-1-ol
• CAS: 210408-09-6
• 化学式: C₁₂H₁₆ClNO
• 分子量: 225.718
• InChiKey: SMZOTNOHERXFMO-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  Acetic acid (1S,2S)-2-(4-chloro-phenylamino)-cyclohexyl ester 在 dipotassium hydrogenphosphate 、 pig liver esterase 、 K₂HPO₄ buffer 作用下， 以 二甲基亚砜 为溶剂， 反应 4.5h， 以46%的产率得到2-(4-chlorophenylamino)cyclohexanol
  参考文献：
  名称：

  Enantiomerically pure N-aryl-β-amino alcohols by enzymatic resolution

  摘要：

  N-Aryl-beta-amino acetates, obtained by opening epoxides with aromatic amines followed by acetylation of the hydroxyl group, were resolved using crude pig liver esterase (PLE) enzyme in DMSO in high enantiomeric excess. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00401-2

文献信息

• STRONGLY LEWIS ACIDIC METAL-ORGANIC FRAMEWORKS FOR CONTINUOUS FLOW CATALYSIS
  申请人：The University of Chicago

  公开号：US20210053042A1

  公开（公告）日：2021-02-25

  Lewis acidic metal-organic framework (MOF) materials comprising triflate-coordinated metal nodes are described. The materials can be used as heterogenous catalysts in a wide range of organic group transformations, including Diels-Alder reactions, epoxide-ring opening reactions, Friedel-Crafts acylation reactions and alkene hydroalkoxylation reactions. The MOFs can also be prepared with metallated organic bridging ligands to provide heterogenous catalysts for tandem reactions and/or prepared as composites with support particles for use in columns of continuous flow reactor systems. Methods of preparing and using the MOF materials and their composites are also described.

  描述了包含三氟甲磺酸盐配位金属节点的Lewis酸性金属有机框架（MOF）材料。这些材料可用作广泛范围的有机基团转化中的杂质催化剂，包括Diels-Alder反应、环氧化物开环反应、Friedel-Crafts酰化反应和烯烃水解烷氧基化反应。这些MOF还可以通过金属化有机桥联配体制备，以提供串联反应的杂质催化剂和/或与支撑颗粒制备为复合材料，用于连续流反应器系统的柱中。还描述了制备和使用MOF材料及其复合材料的方法。
• Magnetic Nano Fe3O4 Catalyzed Solvent-Free Stereo- and Regioselective ­Aminolysis of Epoxides by Amines; a Green Method for the Synthesis of β-Amino Alcohols
  作者：Srinivasarao Babu、Amit Kumar、Ramarao Parella

  DOI：10.1055/s-0033-1340844

  日期：——

  We report the use of magnetic nano Fe3O4 as a mild heterogeneous catalyst for the aminolysis of epoxides with amines. The approach constitutes a green method for the formation of a variety of β-amino alcohols with very high stereo- and regioselectivity under solvent-free and ambient reaction conditions. The aminolysis of chiral epoxides with amines gave the corresponding chiral β-amino alcohols with

  我们报告了使用磁性纳米 Fe3O4 作为温和的多相催化剂，用于环氧化物与胺的氨解。该方法构成了一种在无溶剂和环境反应条件下形成具有非常高立体选择性和区域选择性的各种 β-氨基醇的绿色方法。手性环氧化物与胺的氨解得到相应的手性 β-氨基醇，立体化学完全反转。磁性纳米 催化剂易于回收和循环利用。
• Graphite oxide catalyzed synthesis of $\beta $-amino alcohols by ring-opening of epoxides
  作者：Maryam MIRZA-AGHAYAN、Farzaneh ALVANDI、Mahdieh MOLAEE TAVANA、Rabah BOUKHERROUB

  DOI：10.3906/kim-1604-45

  日期：——

  Graphite oxide as a heterogeneous and recyclable solid acid catalyzed a simple and efficient method for the synthesis of $\beta $-amino alcohols by ring opening of epoxides with amines. This method is effective with various aromatic and aliphatic amines under solvent-free conditions. The corresponding $\beta $-amino alcohols are obtained in high yields (56%-95%) and short reaction times (15-30 min) with high regio- and chemoselectivity under metal-free conditions.

  石墨烯氧化物作为一种异质且可回收的固体酸，催化了一种简单高效的方法，通过环氧化物与胺的开环反应合成$\beta$-氨基醇。该方法在无溶剂条件下，对各种芳香族和脂肪族胺均有效。在无金属条件下，所得$\beta$-氨基醇的产率高（56%-95%），反应时间短（15-30分钟），且具有高区域选择性和化学选择性。
• Vanadium-Salan Catalyzed Enantioselective Ring Opening of <i>meso</i>-Epoxides with Aromatic Amines
  作者：Jiangtao Sun、Chengjian Zhu、Zhenya Dai、Minghua Yang、Xu Pan

  DOI：10.1055/s-2008-1067109

  日期：——

  The first example of enantioselective ring-opening of meso-epoxides catalyzed by chiral oxovanadium(V)-salan complexes is reported. The reaction furnished 1,2-aminoalcohols in good yields and moderate to high enantioselectivities (up to 87%).

  报道了手性氧钒(V)-salan 配合物催化内消旋环氧化物的对映选择性开环的第一个例子。该反应以良好的收率和中等至高的对映选择性（高达 87%）提供了 1,2-氨基醇。
• 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。