(R,R)-4-methyl-N-{2-[(pyridin-2-ylmethylene)amino]cyclohexyl}benzenesulfonamide | 1256652-62-6

• 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: (R,R)-4-methyl-N-{2-[(pyridin-2-ylmethylene)amino]cyclohexyl}benzenesulfonamide
• CAS: 1256652-62-6
• 化学式: C₁₉H₂₃N₃O₂S
• 分子量: 357.477
• InChiKey: TZVTVLKFCPMUAY-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  71.42
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R,R)-4-methyl-N-{2-[(pyridin-2-ylmethylene)amino]cyclohexyl}benzenesulfonamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以61%的产率得到(R,R)-4-methyl-N-{2-[(pyridin-2-ylmethyl)-amino]cyclohexyl}benzenesulfonamide
  参考文献：
  名称：

  Use of tridentate TsDPEN/pyridine ligands in ruthenium-catalysed asymmetric reduction of ketones

  摘要：

  A series of enantiomerically pure tridentate ligands based on the 1,2-diphenylethane-1,2-diamine structure, containing additional pyridine groups, was prepared and tested in asymmetric transfer hydrogenation of ketones using Ru-3(CO)(12) as a metal source. Alcohols were formed in up to 93% ee in the best cases, and good results were obtained with ortho-haloarylketones. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.141
• 作为产物：
  描述：

  吡啶-2-甲醛 、 (R,R)-(-)-N-(4-toluenesulfonyl)-1,2-diaminocyclohexane 以 二氯甲烷 为溶剂， 以87%的产率得到(R,R)-4-methyl-N-{2-[(pyridin-2-ylmethylene)amino]cyclohexyl}benzenesulfonamide
  参考文献：
  名称：

  Use of tridentate TsDPEN/pyridine ligands in ruthenium-catalysed asymmetric reduction of ketones

  摘要：

  A series of enantiomerically pure tridentate ligands based on the 1,2-diphenylethane-1,2-diamine structure, containing additional pyridine groups, was prepared and tested in asymmetric transfer hydrogenation of ketones using Ru-3(CO)(12) as a metal source. Alcohols were formed in up to 93% ee in the best cases, and good results were obtained with ortho-haloarylketones. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.141

文献信息

• Synthesis of Tridentate Ligands Based on Chiral Diamines and Their Application to Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes
  作者：Mei Wu、Shoufeng Wang、Chungu Xia、Wei Sun

  DOI：10.1002/cjoc.201090243

  日期：——

  A new type of chiral tridentate ligands were prepared and their Zn complexes were examined for the asymmetric Friedel‐Crafts alkylation of indoles with nitroalkenes, which gave rise to good yields and moderate enantioselectivities.

  制备了一种新型的手性三齿配体，并研究了其锌配合物对吲哚与硝基烯烃的不对称弗里德-克来福特烷基化反应的影响，从而获得了良好的收率和中等的对映选择性。
• Application of rapidly generated bidentate ligand libraries to zinc catalyzed reductions
  作者：Tariq Zaman、Robin Frauenlob、Robert McCarthy、Carolyn M. Walsh、Enda Bergin

  DOI：10.1016/j.jorganchem.2012.06.013

  日期：2012.10

  A methodology for the combinatorial synthesis of bidentate ligands - allowing direct screening of reaction products without the need for isolation or purification - has been employed in a zinc catalyzed hydrosilylation. This reaction allowed the robustness of the methodology to be examined, by employing it in a challenging case where the metal complex is not pre-formed prior to catalysis. Four different ligand families have been examined: imines, aminals, bis-imines and oxazolines and related compounds, with a small library of each type produced and directly screened in the reaction. Three ligands providing enantioselectivities of 50% or more in this very challenging reaction were identified, and ees and conversions were equivalent whether the ligand was obtained as a crude mixture from a library synthesis or as an isolated, purified compound. (C) 2012 Elsevier B.V. All rights reserved.