(2R,1’R)-2-[(4-nitrophenyl)(phenylamino)methyl]cyclohexanone | 1393116-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,1’R)-2-[(4-nitrophenyl)(phenylamino)methyl]cyclohexanone
• 英文别名: (R)-2-((R)-(4-nitrophenyl)(phenylamino)methyl)cyclohexanone；(R)-2-[(R)-4-nitrophenyl(N-phenylamino)methyl]cyclohexanone；(2R)-2-[(R)-anilino-(4-nitrophenyl)methyl]cyclohexan-1-one
• CAS: 1393116-30-7
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: NYIIUYQEHABPRN-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环己酮 、 对硝基苯甲醛 、 苯胺 在 (-)-4,5-dimethyl-3,6-bis(o-tolyl)-1,2-benzenedisulfonimide 作用下， 反应 36.0h， 以89%的产率得到(2R,1’R)-2-[(4-nitrophenyl)(phenylamino)methyl]cyclohexanone
  参考文献：
  名称：

  Brønsted acid catalyzed enantio- and diastereoselective one-pot three component Mannich reaction

  摘要：

  A chiral derivative of 1,2-benzenedisulfonimide,(-)-4,5-dimethy1-3,6-bis(o-toly1)-1,2-benzenedisulfonimide is herein proven to be an efficient chiral catalyst in a one pot three-component Mannich protocol. Reaction conditions are mild and green, while the enantio- and diastereoselectivity are excellent. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.09.006

文献信息

• Direct Asymmetric Mannich Reaction Catalyzed by a d-Glucosamine-Derived Organocatalyst
  作者：Rama Peddinti、Arun Sharma

  DOI：10.1055/s-0036-1591740

  日期：2018.3

  Sugar-based primary amines have been employed as organocatalysts for the direct asymmetric Mannich reaction. By catalyst-screening experiments, we observed that catalysts bearing a hydroxy function at C-3 actively participated in the reaction, possibly through hydrogen bonding with the imine generated in situ, to provide β-amino carbonyl compounds with better diastereoselectivity and enantioselectivity

  糖基伯胺已被用作直接不对称曼尼希反应的有机催化剂。通过催化剂筛选实验，我们观察到在 C-3 处带有羟基官能团的催化剂积极参与反应，可能是通过与原位生成的亚胺形成氢键，从而提供具有更好非对映选择性和对映选择性的 β-氨基羰基化合物。获得的所有产品都处于良好至极好的对映体过量。
• Diastereoselective Mannich reaction with prolinated MWCNTs as a heterogeneous organo-nanocatalyst
  作者：Mahsa Khoshnevis、Hossein Eshghi

  DOI：10.1007/s12039-020-1740-4

  日期：2020.12

  Mannich reaction. The results hold out improvements in stereoselectivity, ease of separating and reusability. Graphic Abstract This work represents an efficient and simple method to prepare Prolinated- MWCNTs as a heterogeneous organo-nanocatalyst. Prolinated-MWCNT was characterized by different analyses. The efficiency and catalytic activity of Pro-MWCNTs have investigated in mannich reaction, which

  摘要 我们打算通过脯氨酸多壁碳纳米管将脯氨酸作为均相催化剂转化为非均相催化剂，以通过简化分离，催化经济性，可重复使用性等方式提高脯氨酸作为催化剂的效率。为了实现这些目标，我们勾勒了脯氨酸-MWCNT催化剂并进行了表征通过不同的分析（例如FT-IR，SEM，EDX，CHNS）进行分析。研究了这种非均相催化剂的效率，并与脯氨酸均相催化剂在曼尼希反应中的效率进行了比较。结果证明了立体选择性，易于分离和可重用性方面的改进。 图形摘要 这项工作代表了一种高效简单的方法来制备脯氨酸多壁碳纳米管，将其作为非均相有机纳米催化剂。脯氨酸MWCNT的特征在于不同的分析。Pro-MWCNTs的效率和催化活性已在曼尼希反应中进行了研究，与母体脯氨酸催化剂相比，非对映选择性，中等对映选择性，良好的重用性和高收率。
• Double axially chiral bisphosphorylimides as novel Brønsted acids in asymmetric three-component Mannich reaction
  作者：Ying-Ying Chen、Yi-Jun Jiang、Yan-Sen Fan、Di Sha、Qifeng Wang、Guangliang Zhang、Liangyu Zheng、Suoqin Zhang

  DOI：10.1016/j.tetasy.2012.06.008

  日期：2012.6

  A double axially chiral bisphosphorylimide has been demonstrated to be an efficient and highly sterically hindered Bronsted acid in asymmetric three-component Mannich reactions. Optically active syn-beta-amino ketones were obtained in high yields (up to 99%) with excellent diastereoselectivity (99:1) and enantioselectivity (up to 99% ee). A gram-scale reaction was also performed to prove the synthetic application value of this reaction. (c) 2012 Elsevier Ltd. All rights reserved.
• Enzyme-catalyzed asymmetric Mannich reaction using acylase from Aspergillus melleus
  作者：Zhi Guan、Jian Song、Yang Xue、Da-Cheng Yang、Yan-Hong He

  DOI：10.1016/j.molcatb.2014.11.007

  日期：2015.1

  Acylase I from Aspergillus melleus (AMA) displayed catalytic promiscuity towards one-pot asymmetric Mannich reaction in acetonitrile for the first time. AMA showed favourable catalytic activity with good adaptability to different substrates. The activity and stereoselectivity of the enzyme could be improved by adjusting solvent, pH, water content, temperature, molar ratio of substrates and enzyme loading. The enantioselectivities up to 89% ee, diastereoselectivities up to 90:10 dr (syn/anti) and yields up to 82% were achieved. This work offered a novel case of enzyme catalytic promiscuity and a potential synthetic method for organic chemistry. (C) 2014 Elsevier B.V. All rights reserved.
• Brønsted acid catalyzed enantio- and diastereoselective one-pot three component Mannich reaction
  作者：Margherita Barbero、Silvano Cadamuro、Stefano Dughera

  DOI：10.1016/j.tetasy.2015.09.006

  日期：2015.11

  A chiral derivative of 1,2-benzenedisulfonimide,(-)-4,5-dimethy1-3,6-bis(o-toly1)-1,2-benzenedisulfonimide is herein proven to be an efficient chiral catalyst in a one pot three-component Mannich protocol. Reaction conditions are mild and green, while the enantio- and diastereoselectivity are excellent. (C) 2015 Elsevier Ltd. All rights reserved.