N-(α-tosylbenzyl)-cyclohexanecarboxamide | 372199-81-0

• 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-(α-tosylbenzyl)-cyclohexanecarboxamide
• 英文别名: N-[(4-methylphenylsulfonyl)(phenyl)methyl]cyclohexanecarboxamide；Cyclohexanecarboxamide, N-[[(4-methylphenyl)sulfonyl]phenylmethyl]-；N-[(4-methylphenyl)sulfonyl-phenylmethyl]cyclohexanecarboxamide
• CAS: 372199-81-0
• 化学式: C₂₁H₂₅NO₃S
• 分子量: 371.5
• InChiKey: CVZNABCKOOAIOS-UHFFFAOYSA-N

物化性质

• 沸点：
  626.5±55.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  肉桂醛 、 N-(α-tosylbenzyl)-cyclohexanecarboxamide 在 3-苄基羟乙基甲基噻唑氯化锂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到N-(2-oxo-1,4-diphenyl-trans-but-3-enyl)-cyclohexanecarboxamide
  参考文献：
  名称：

  通过有机催化合成α-酰胺基酮：噻唑鎓催化的醛与嘧啶的交叉偶联。

  摘要：

  DOI：

  10.1021/ja0165943
• 作为产物：
  描述：

  苯甲醛 、 环己甲酰胺 、 sodium 4-methylbenzenesulfinate 在 三甲基氯硅烷 作用下， 以 乙腈 为溶剂， 生成 N-(α-tosylbenzyl)-cyclohexanecarboxamide
  参考文献：
  名称：

  通过有机催化合成α-酰胺基酮：噻唑鎓催化的醛与嘧啶的交叉偶联。

  摘要：

  DOI：

  10.1021/ja0165943

文献信息

• Sustainable, green protocols for heterogenized organocatalysts: N-Phenylthiazolium salts heterogenized on organic–inorganic hybrid mesoporous supports
  作者：Sankaranarayanapillai Shylesh、Zhou Zhou、Qingguo Meng、Alex Wagener、Andreas Seifert、Stefan Ernst、Werner R. Thiel

  DOI：10.1016/j.molcata.2010.08.022

  日期：2010.11.1

  A heterogenized organocatalyst was synthesized by the covalent anchoring of N-phenyl-thiazolium salts over mesoporous organosilica (phenylene-silica, ethane-silica) and mesoporous silica (MCM-41) supports. Powder X-ray diffraction patterns as well as nitrogen physisorption analysis confirmed the retention of mesoporous structure after the grafting reactions. Solid-state NMR analysis (C-13 CP-MAS NMR, Si-29 MAS NMR) certified the integrity of organocatalyst residing inside the pore channels of the mesoporous supports. Catalytic evaluation in the benzoin condensation reaction as well as in the cross-coupling of aldehydes with acyl imines indicated that the organocatalyst heterogenized on mesoporous phenylene organosilica exhibited higher catalytic activity, stability and reusability than the analogous mesoporous silica support. The better activity and stability of the phenylene-silica support was attributed to the enhanced hydrophobic properties arising from the frame wall organic groups. (C) 2010 Elsevier B.V. All rights reserved.
• Synthesis of Substituted Imidazoles via Organocatalysis
  作者：Doug E. Frantz、Louis Morency、Arash Soheili、Jerry A. Murry、Edward J. J. Grabowski、Richard D. Tillyer

  DOI：10.1021/ol0498803

  日期：2004.3.1

  A one-pot synthesis of substituted imidazoles is described. The cornerstone of this methodology involves the thiazolium-catalyzed addition of an aldehyde to an acyl Imine to generate the corresponding alpha-ketoamide in situ followed by ring closure to the imidazole in a one-pot sequence. The extension of this methodology to the one-pot synthesis of substituted oxazoles and thiazoles is also described.
• Synthesis of α-Amido Ketones via Organic Catalysis:  Thiazolium-Catalyzed Cross-Coupling of Aldehydes with Acylimines
  作者：Jerry A. Murry、Doug E. Frantz、Arash Soheili、Richard Tillyer、Edward J. J. Grabowski、Paul J. Reider

  DOI：10.1021/ja0165943

  日期：2001.10.1