(R)-2-[(R)-phenyl(N-phenylamino)methyl]cyclohexanone | 1357019-96-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-2-[(R)-phenyl(N-phenylamino)methyl]cyclohexanone
• 英文别名: (R)-2-((R)-phenyl(phenylamino)methyl)cyclohexanone；(phenyl(phenylamino)methyl)cyclohexanone；(2R)-2-[(R)-anilino(phenyl)methyl]cyclohexan-1-one
• CAS: 1357019-96-5
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: ITYLIHBJQIGSFJ-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己酮 、 苯甲醛 、 苯胺 在 (11b'R)-4,4'-azanediylbis(2,6-di(naphthalen-1-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide) 作用下， 以 甲苯 为溶剂， 反应 12.5h， 以99%的产率得到(R)-2-[(R)-phenyl(N-phenylamino)methyl]cyclohexanone
  参考文献：
  名称：

  Double axially chiral bisphosphorylimides as novel Brønsted acids in asymmetric three-component Mannich reaction

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2012.06.008

文献信息

• 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。
• 二苯基四氢化双吲哚衍生物催化不对称 Mannich反应的应用
  申请人：常州大学

  公开号：CN108912000B

  公开（公告）日：2020-10-16

  本发明涉及化合物的新应用，特别涉及二苯基四氢化双吲哚衍生物作为不对称Mannich反应催化剂的应用，以芳胺、芳醛和环己酮为原料，二苯基四氢化双吲哚衍生物为催化剂进行Mannich催化反应。本发明的二苯基四氢化双吲哚衍生物合成工艺条件温和、催化效率高，其催化的不对称Mannich反应可获得很好的顺反比，具有广阔的应用前景。
• A Multicomponent Mannich Reaction Catalyzed by Hydrolases Immobilized on Titanate Nanotubes
  作者：Juliane Bessoni Kosctiuk、Matheus Enrique Ribeiro Neto、Gabriela Alcoforado Pereira、Nadia Krieger、Daniela Zambelli Mezalira、Cristiane Pilissão

  DOI：10.1002/cplu.202300698

  日期：——

  This study presents an innovative method for synthesizing β‐amino carbonylated compounds, specifically 2‐[phenyl(phenylamino)methyl] cyclohexanone, achieving high conversions and diastereomeric ratios. Using trypsin or α‐chymotrypsin in both free and immobilized forms on titanate nanotubes (NtsTi), synthesized through alkaline hydrothermal methods, successful immobilization yields were attained. Notably, α‐chymotrypsin, when free, displayed a diastereoselective synthesis of the anti‐isomer with 97 % conversion and 16 : 84 (syn : anti) diastereomeric ratio, which slightly decreased upon immobilization on NtsTi. Trypsin, in its free form, exhibited diastereoselective recognition of the syn‐isomer, while immobilization on NtsTi (trypsin/NtsTi) led to an inversion of diastereomeric ratio. Both trypsin/NtsTi and α‐chymotrypsin/NtsTi demonstrated significant catalytic efficiency over five cycles. In conclusion, NtsTi serves as an effective support for trypsin and α‐chymotrypsin immobilization, presenting promising prospects for diastereoselective synthesis and potential industrial applications. Furthermore, it offers promising prospects for the diastereoselective synthesis of 2‐[phenyl(phenylamino)methyl] cyclohexanone through multicomponent Mannich reaction and future industrial application.

  摘要 本研究提出了一种合成β-氨基羰基化合物（特别是 2-[苯基（苯基氨基）甲基]环己酮）的创新方法，实现了高转化率和非对映异构比。使用通过碱性水热法合成的钛酸纳米管（NtsTi）上的游离和固定形式的胰蛋白酶或α-糜蛋白酶，成功地获得了固定化产量。值得注意的是，α-糜蛋白酶在游离状态下可以非对映选择性地合成反异构体，转化率为 97%，非对映异构体比例为 16:84（同：反），固定在 NtsTi 上后，非对映异构体比例略有下降。游离状态下的胰蛋白酶对合成异构体具有非对映选择性识别，而固定在 NtsTi 上（胰蛋白酶/NtsTi）则导致非对映异构体比例倒置。在五个循环中，胰蛋白酶/NtsTi 和 α-糜蛋白酶/NtsTi 都表现出显著的催化效率。总之，NtsTi 是固定胰蛋白酶和 α-糜蛋白酶的有效支持物，为非对映选择性合成和潜在的工业应用提供了广阔的前景。此外，它还为通过多组分曼尼希反应非对映选择性合成 2-[苯基（苯基氨基）甲基]环己酮以及未来的工业应用提供了广阔的前景。
• 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.
• 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.