N-(1R,2R)-(2-aminocyclohexyl)-4-(trifluoromethyl)benzenesulfonamide | 936110-78-0

• 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: N-(1R,2R)-(2-aminocyclohexyl)-4-(trifluoromethyl)benzenesulfonamide
• 英文别名: N-[(1R,2R)-2-aminocyclohexyl]-4-(trifluoromethyl)benzenesulfonamide
• CAS: 936110-78-0
• 化学式: C₁₃H₁₇F₃N₂O₂S
• 分子量: 322.351
• InChiKey: BVWSICOXCYKXPN-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(1R,2R)-(2-aminocyclohexyl)-4-(trifluoromethyl)benzenesulfonamide 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 48.0h， 生成 (1S,2R,4R,1'R,2'R)-N-{trans-2'-[(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methylsulfonylamino]cyclohexyl}-4''-(trifluoromethyl)benzenesulfonamide
  参考文献：
  名称：

  First catalytic enantioselective synthesis of the cocaine abuse therapeutic agent (S)-(+)-1-(4-{2-[bis(4-fluorophenyl)methoxy]ethyl}piperazin-1-yl)-2-phenyl-2-propanol

  摘要：

  (S)-(+)-1-(4-{2-[Bis(4-fluorophenyl)methoxy]ethyl} piperazin-1-yl)-2-phenyl-2-propanol, which is a promising candidate as a cocaine abuse therapeutic agent, is prepared in several steps. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to either 2-chloro or 2-bromoacetophenone catalyzed by the use of different chiral isoborneolsulfonamide ligands in the presence of titanium tetraisopropoxide. The synthesis of a new isoborneolsulfonamide ligand bearing a trifluromethyl. substituent and its use in this addition is also presented. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.028
• 作为产物：
  描述：

  4-三氟甲基苯磺酰氯 、 (R,R)-1,2-diaminocyclohexane tartrate 在 sodium hydroxide 、 三乙胺 作用下， 以96%的产率得到N-(1R,2R)-(2-aminocyclohexyl)-4-(trifluoromethyl)benzenesulfonamide
  参考文献：
  名称：

  Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane

  摘要：

  A series of aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane were synthesized with electron withdrawing and donating groups. These were complexed with Rh(Cp*) or Ru(arene) and their catalytic efficiencies were compared in the ATH of acetophenone using sodium formate/water or isopropanol/KOH as the hydrogen source. Results suggest that substituents on the benzene ring of the sulfonamide have very little electronic impact on the enantioselectivity and mechanism of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.036

文献信息

• Auxiliary‐Free Remote Dearomatizative Nitrenoid Transfer for Enantioselective Construction of Spirolactams
  作者：Bo‐Han Zhu、Wen‐Ting Guo、Qing Sun、Peng‐Cheng Qian、Long‐Wu Ye、Long Li

  DOI：10.1002/adsc.202101189

  日期：2022.1.18

  An Ir-catalyzed remote dearomatizative amidation for the enantioselective construction of chiral spirolactams in 70–93% yield with 81–96% ee was developed. This protocol represented a more atom-economical approach to chiral spirolactams via Ir-catalyzed nitrenoid transfer without the introduction of a traceless O-silyl achiral auxiliary.

  开发了一种 Ir 催化的远程脱芳构酰胺化，用于手性螺内酰胺的对映选择性构建，产率为 70-93%，ee 为 81-96%。该协议代表了一种更原子经济的手性螺内酰胺方法，通过 Ir 催化的 nitrenoid 转移而无需引入无痕 O-甲硅烷基非手性助剂。
• Asymmetric addition of diethylzinc to benzaldehyde catalyzed by novel chiral C2-symmetric tetrakis(sulfonamide)–titanium(IV) complexes
  作者：Antonio Venegas、Lucrecia Rivas、Gabriela Huelgas、Cecilia Anaya de Parrodi、Domingo Madrigal、Gerardo Aguirre、Miguel Parra-Hake、Daniel Chávez、Ratnasamy Somanathan

  DOI：10.1016/j.tetasy.2010.11.023

  日期：2010.12

  A series of chiral C-2-symmetric tetrakis(sulfonamides) 3a-f, 4a-f were prepared and employed as ligands for titanium(IV) complexes in the asymmetric addition of diethylzinc to benzaldehyde. The chiral secondary alcohols were obtained in high yields and in moderate enantioselectivities. (C) 2010 Elsevier Ltd. All rights reserved.
• First catalytic enantioselective synthesis of the cocaine abuse therapeutic agent (S)-(+)-1-(4-{2-[bis(4-fluorophenyl)methoxy]ethyl}piperazin-1-yl)-2-phenyl-2-propanol
  作者：Vicente J. Forrat、Diego J. Ramón、Miguel Yus

  DOI：10.1016/j.tetasy.2006.12.028

  日期：2007.2

  (S)-(+)-1-(4-2-[Bis(4-fluorophenyl)methoxy]ethyl} piperazin-1-yl)-2-phenyl-2-propanol, which is a promising candidate as a cocaine abuse therapeutic agent, is prepared in several steps. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to either 2-chloro or 2-bromoacetophenone catalyzed by the use of different chiral isoborneolsulfonamide ligands in the presence of titanium tetraisopropoxide. The synthesis of a new isoborneolsulfonamide ligand bearing a trifluromethyl. substituent and its use in this addition is also presented. (c) 2007 Elsevier Ltd. All rights reserved.
• Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane
  作者：Norma A. Cortez、Gerardo Aguirre、Miguel Parra-Hake、Ratnasamy Somanathan

  DOI：10.1016/j.tetasy.2008.04.036

  日期：2008.6

  A series of aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane were synthesized with electron withdrawing and donating groups. These were complexed with Rh(Cp*) or Ru(arene) and their catalytic efficiencies were compared in the ATH of acetophenone using sodium formate/water or isopropanol/KOH as the hydrogen source. Results suggest that substituents on the benzene ring of the sulfonamide have very little electronic impact on the enantioselectivity and mechanism of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.