(1R,2R)-2-phenylamino-1-cyclohexanol | 110716-75-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R)-2-phenylamino-1-cyclohexanol
• 英文别名: (1R,2R)-2-(phenylamino)cyclohexanol；(1R,2R)-2-(phenylamino)cyclohexan-1-ol；(-)-2-(phenylamino)cyclohexanol；trans-2-Phenylaminocyclohexanol；(1R,2R)-2-anilinocyclohexan-1-ol
• CAS: 110716-75-1
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: ABSZYEUMTNJQPI-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 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

• 作为反应物：
  描述：

  (1R,2R)-2-phenylamino-1-cyclohexanol 、 硫酸二甲酯 、 potassium carbonate 以94%的产率得到
  参考文献：
  名称：

  YAMASHITA HIROYUKI, CHEM. LETT.,(1987) N 3, 525-528

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(N-ethyl-anilino)-cyclohexanone 以8%的产率得到
  参考文献：
  名称：

  EL-HAMAMY, AHMAD, A.;HILL, J.;TOWNEND, J., J. CHEM. SOC. PERKIN TRANS., 1983, N 3, 573-580

  摘要：

  DOI：

文献信息

• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• 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。
• 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。
• Asymmetric Amination of meso-Epoxide with Vegetable Powder as a Low-Toxicity Catalyst
  作者：Yuki Takeuchi、Tatsuhiro Asano、Kazuya Tsuzaki、Koichi Wada、Hiroyuki Kurata

  DOI：10.3390/molecules25143197

  日期：——

  This paper describes the scope and limitation of substrates subjected to asymmetric amination with epoxides catalyzed by a soluble soybean polysaccharide (Soyafibe S-DN), which we recently discovered from the reaction of 1,2-epoxycyclohexane with cyclopropylamine. Various meso-epoxides reacted with various amines afforded the corresponding products with good enantiomeric selectivity. Since it was found that pectin was found to have a catalytic ability after screening commercially available polysaccharides, we studied 33 different vegetable powders having pectic substances, and we found that many vegetable powders showed catalytic ability. These results should guide in using vegetable components as low-toxic catalysts for the production of pharmaceuticals.

  本文描述了由可溶性大豆多糖（Soyafibe S-DN）催化的环氧化合物与环丙胺不对称胺化反应所受限的基质范围和限制性。我们最近从1,2-环氧环己烷与环丙胺反应中发现了这种多糖。各种中间体环氧化合物与各种胺反应产生了相应的产物，具有良好的对映选择性。在筛选商业可获得的多糖后发现果胶具有催化能力后，我们研究了33种含有果胶物质的不同蔬菜粉末，发现许多蔬菜粉末显示出催化能力。这些结果应该指导在制药生产中使用蔬菜成分作为低毒性催化剂。
• Highly Enantioselective Syntheses of Chiral β-Amino Alcohols in the Presence of Chiral TiIV Schiff Base Complexes as Catalysts
  作者：Rukhsana I. Kureshy、K. Jeya Prathap、Santosh Agrawal、Noor-ul H. Khan、Sayed H. R. Abdi、Raksh V. Jasra

  DOI：10.1002/ejoc.200800099

  日期：2008.6

  3′-dimethyl-5,5′-methylenebis(salicylaldehyde) with (1R,2S)-(–)-2-aminodiphenylethanol and were characterized by elemental analysis, 1H NMR, 13C NMR, IR, UV/Vis, and CD spectroscopy, optical rotation, and mass spectrometry. Highly enantioselective ring opening reactions of meso-stilbene oxide, cyclohexene oxide, cyclooctene oxide, and cis-butene oxide with anilines in the presence of several additives were carried

  通过3,3'-二叔丁基-5,5'-亚甲基双(水杨醛)和3,3'-二甲基-5,5'-亚甲基双(水杨醛)缩合制备了两种新的手性席夫碱1和2用 (1R,2S)-(-)-2-氨基二苯乙醇进行表征，并通过元素分析、1H NMR、13C NMR、IR、UV/Vis 和 CD 光谱、旋光度和质谱进行表征。在通过 Ti(OiPr) 相互作用原位生成的 TiIV 配合物的存在下，在几种添加剂的存在下进行了内消旋二苯乙烯氧化物、环己烯氧化物、环辛烯氧化物和顺丁烯氧化物与苯胺的高度对映选择性开环反应4 与手性希夫碱 1 和 2 在 0 °C 下。当手性亚胺用作添加剂时，在 10 小时内实现了具有高对映选择性（ee，> 99 %）的手性 β-氨基醇的优异产率（> 99 %）。就环氧化物开环反应生成高光学纯度手性β-氨基醇的反应性和对映选择性而言，催化剂1-Ti(OiPr)4比催化剂2-Ti(OiPr)4更好。本研