(1R,2R)-4-methyl-N-(2-(piperidin-1-yl)-cyclohexyl)-benzenesulfonamide | 1043450-07-2

• 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: (1R,2R)-4-methyl-N-(2-(piperidin-1-yl)-cyclohexyl)-benzenesulfonamide
• 英文别名: 4-methyl-N-[(1R,2R)-2-piperidin-1-ylcyclohexyl]benzenesulfonamide
• CAS: 1043450-07-2
• 化学式: C₁₈H₂₈N₂O₂S
• 分子量: 336.499
• InChiKey: IJNJWOMHEXKCRW-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,5-二碘戊烷 、 (1R,2R)-(-)-N-对甲苯磺酰基-1,2-环己二胺 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以58%的产率得到(1R,2R)-4-methyl-N-(2-(piperidin-1-yl)-cyclohexyl)-benzenesulfonamide
  参考文献：
  名称：

  Synthesis of a series of novel N,N-dialkyl-TsDPEN ligands and their application to enantioselective addition of dialkylzinc to benzaldehyde

  摘要：

  A series of mono- and dialkylated derivatives of C2-symmetric N-tosyl-1,2-diphenylethylene diamines have been prepared and used as ligands for the enantiomeric control of the addition of diethylzinc to aldehydes. Addition products of up to 79% ee were formed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.020

文献信息

• <i>trans</i>-1,2-Diaminocyclohexane-based sulfonamides as effective hydrogen-bonding organocatalysts for asymmetric Michael–hemiacetalization reaction
  作者：Maciej Dajek、Rafał Kowalczyk、Przemysław J. Boratyński

  DOI：10.1039/c8cy01199k

  日期：——

  bifunctional monosulfonamide derivative of DACH was an effective catalyst for Michael addition–hemiacetalization reactions, providing products with ees exceeding 99% under optimized conditions. High enantioselectivities were achieved with just 0.2% mol catalyst loading. The sulfonamide outperformed analogous thiourea and squaramide-based organocatalysts.

  一种易于获得的DACH双官能单磺酰胺衍生物是迈克尔加成-半缩醛化反应的有效催化剂，可在优化条件下提供ee超过99％的产品。仅催化剂负载量为0.2％mol时，就可以实现高对映选择性。磺酰胺的性能优于类似的硫脲和方胺基有机催化剂。