2-(4-methoxyphenylamino)cyclohexanone | 27904-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenylamino)cyclohexanone
• 英文别名: 2-p-anisidino-cyclohexanone；2-p-Anisidino-cyclohexanon；2-(4-Methoxyanilino)cyclohexanone；2-(4-methoxyanilino)cyclohexan-1-one
• CAS: 27904-56-9
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: LTZCUDNVQLDYPS-UHFFFAOYSA-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：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenylamino)cyclohexanone 在 三仲丁基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (1R,2S)-2-(4-methoxyphenylamino)cyclohexanol
  参考文献：
  名称：

  Molecular Modeling and Anticholinesterasic Activity of Novel 2-ArylaminocyclohexylN,N-Dimethylcarbamates

  摘要：

  This work reports a detailed theoretical and experimental study of the novel isomer series cis- and trans-2-arylaminocyclohexyl N,N-dimethylcarbamates as potential inhibitors of cholinesterases. In vitro inhibition assay by Ellman's method with human blood samples showed that the new carbamates are selective to the inhibition of enzyme butyrylcholinesterase (BuChE) with maximum inhibition of 90% and IC50 of 6 and 8 mmol L-1 for the more actives compounds of the series. Molecular modeling studies point to significant differences for the conformations of the compounds in the active sites of enzymes BuChE and acetylcholinesterase (AChE). The results show that the compounds interact more effectively with the active site of enzyme BuChE since the carbamate group is close to the key residues of the catalytic triad.

  DOI：

  10.5935/0103-5053.20130225
• 作为产物：
  描述：

  环己酮 在 喹啉 、 溴 、 sodium carbonate 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 2.0h， 生成 2-(4-methoxyphenylamino)cyclohexanone
  参考文献：
  名称：

  Molecular Modeling and Anticholinesterasic Activity of Novel 2-ArylaminocyclohexylN,N-Dimethylcarbamates

  摘要：

  This work reports a detailed theoretical and experimental study of the novel isomer series cis- and trans-2-arylaminocyclohexyl N,N-dimethylcarbamates as potential inhibitors of cholinesterases. In vitro inhibition assay by Ellman's method with human blood samples showed that the new carbamates are selective to the inhibition of enzyme butyrylcholinesterase (BuChE) with maximum inhibition of 90% and IC50 of 6 and 8 mmol L-1 for the more actives compounds of the series. Molecular modeling studies point to significant differences for the conformations of the compounds in the active sites of enzymes BuChE and acetylcholinesterase (AChE). The results show that the compounds interact more effectively with the active site of enzyme BuChE since the carbamate group is close to the key residues of the catalytic triad.

  DOI：

  10.5935/0103-5053.20130225

文献信息

• Highly Enantioselective Synthesis of Chiral Cyclic Amino Alcohols and Conhydrine by Ruthenium-Catalyzed Asymmetric Hydrogenation
  作者：Sheng Liu、Jian-Hua Xie、Wei Li、Wei-Ling Kong、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1021/ol901605a

  日期：2009.11.5

  A highly efficient enantio- and diastereoselective synthesis of chiral cis-β-N-alkyl/arylamino cyclic alcohols has been realized by asymmetric hydrogenation of racemic α-amino cyclic ketones via DKR catalyzed by [RuCl2((S)-Xyl-SDP)((R,R)-DPEN)]. The enantioselectivities of the reaction were up to 99.9% ee with 99:1 cis-selectivities. A practical catalytic asymmetric synthesis of all four isomers of

  一个高效对映和非对映选择性合成的手性顺式-β- ñ -烷基/芳基氨基环醇已经由外消旋的不对称氢化实现α氨基经由DKR环酮催化通过将[RuCl 2（（小号）-Xyl-SDP） （（R，R）-DPEN）]。该反应的对映选择性分别达到99.9％ee的用99：1分的顺式-选择性。还开发了一种实用的催化方法，可合成水合所有四个异构体。
• Catalytic enantioselective Amadori–Heyns rearrangement of racemic α-hydroxy ketones with arylamines: synthesis of optically active α-arylamino ketones
  作者：Angelo Frongia、Francesco Secci、Francesca Capitta、Pier Paolo Piras、Maria Luisa Sanna

  DOI：10.1039/c3cc45278f

  日期：——

  A novel synthesis of optically active alpha-arylamino ketones through an organocatalytic enantioselective Amadori-Heyns rearrangement is described.

  描述了一种通过有机催化对映选择性Amadori-Heyns重排的新型光学活性α-芳基氨基酮的合成方法。
• Rh‐Catalyzed Chemodivergent [3+3] Annulations of Diazoenals and α‐Aminoketones: Direct Synthesis of Functionalized 1,2‐Dihydropyridines and Fused 1,4‐Oxazines
  作者：Pratap Kumar Mandal、Sreenivas Katukojvala

  DOI：10.1002/chem.202303862

  日期：2024.4.2

  Chemodivergent [3+3] annulations: The reactivity of Rh-enalcarbenoid has been switched from carbenoid to vinylogous NH-insertion by altering acyclic to cyclic α-amino ketones to deliver functionalized 1,2-dihydropyridines (1,2-DHPs) and fused 1,4-oxazines respectively. The structural diversification of 1,2-DHP and fused 1,4-oxazines gave valuable piperidines, pyrido[1,2-a]indole, 2-pyridone, hexahydroquinolin-2(1H)-ones

  化学发散 [3+3] 环化：通过将无环 α-氨基酮改变为环状 α-氨基酮，Rh-enalcarbenoid 的反应性已从类胡萝卜素转变为插烯 NH-插入，以提供功能化的 1,2-二氢吡啶 (1,2-DHP) 和融合分别为1,4-恶嗪。 1,2-DHP和稠合1,4-恶嗪的结构多样化得到有价值的哌啶、吡啶并[1,2-a]吲哚、2-吡啶酮、六氢喹啉-2( 1H )-酮、六氢喹啉和四氢喹啉酮。
• Xu; Chen; Liu, Asian Journal of Chemistry, 2011, vol. 23, # 9, p. 4165 - 4168
  作者：Xu、Chen、Liu、Ren、Zhou、Lu

  DOI：——

  日期：——
• Kotschetkow; Kudrjaschow, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 248,253; engl. Ausg. S. 277, 281
  作者：Kotschetkow、Kudrjaschow

  DOI：——

  日期：——