(R,R)-N-benzyl-N’-tert-butoxylcarbonyl-1,2-diaminocyclohexane | 958867-32-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R,R)-N-benzyl-N’-tert-butoxylcarbonyl-1,2-diaminocyclohexane
• 英文别名: N-[(1R,2R)-2-(benzylamino)-1,2-diphenylethyl]-4-methylbenzenesulfonamide
• CAS: 958867-32-8
• 化学式: C₂₈H₂₈N₂O₂S
• 分子量: 456.609
• InChiKey: QYQUTSZXRMZKFH-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,R)-N-benzyl-N’-tert-butoxylcarbonyl-1,2-diaminocyclohexane 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(1R,2R)-N-benzyl-N-[1,2-diphenyl-2-(toluene-4-sulfonylamino)-ethyl]acetamide
  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
• 作为产物：
  描述：

  在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以64%的产率得到(R,R)-N-benzyl-N’-tert-butoxylcarbonyl-1,2-diaminocyclohexane
  参考文献：
  名称：

  含三唑的三齿配体钌配合物在酮不对称转移加氢中的应用

  摘要：

  描述了基于与三唑基连接的同手性1,2-二胺结构的一系列三齿配体的合成及其在酮的不对称转移氢化中的后续应用。在最佳情况下，获得的酒精含量高达ee的93％。尽管不需要碱，但是必须使用Ru 3（CO）12作为金属源，这表明形成活性催化剂的独特机理。

  DOI：

  10.1021/ol302354z

文献信息

• Asymmetric hydrogenation of ketones using Ir(III) complexes of N-alkyl-N’-tosyl-1,2-ethanediamine ligands
  作者：José E.D. Martins、David J. Morris、Martin Wills

  DOI：10.1016/j.tetlet.2008.11.101

  日期：2009.2

  The combination of an enantiomerically pure N'-alkylated derivative of N-4-toluenesulfonyl-1,2-diphenylethane-1,2-diamine (TsDPEN) with iridium trichloride results in the formation of a catalyst with high selectivity for ketone hydrogenation. Products with enantiomeric excesses of up to 84% were formed. The best results were obtained using a ligand with an n-alkyl chain and ortho-substituted acetophenone derivatives and other hindered derivatives. (C) 2008 Elsevier Ltd. All rights reserved.
• Dehydrogenative α-Oxygenation of Ethers with an Iron Catalyst
  作者：Angela Gonzalez-de-Castro、Craig M. Robertson、Jianliang Xiao

  DOI：10.1021/ja502167h

  日期：2014.6.11

  Selective alpha-oxidation of ethers under aerobic conditions is a long-pursued transformation; however, a green and efficient catalytic version of this reaction remains challenging. Herein, we report a new family of iron catalysts capable of promoting chemoselective alpha-oxidation of a range of ethers with excellent mass balance and high turnover numbers under 1 atm of O-2 with no need for any additives. Unlike metalloenzymes and related biomimetics, the catalyst produces H-2 as the only byproduct. Mechanistic investigations provide evidence for an unexpected two-step reaction pathway, which involves dehydrogenative incorporation of O-2 into the ether to give a peroxobisether intermediate followed by cleavage of the peroxy bond to form two ester molecules, releasing stoichiometric H-2 gas in each step. The operational simplicity and environmental friendliness of this methodology affords a useful alternative for performing oxidation, while the unique ability of the catalyst in oxygenating a substrate via dehydrogenation points to a new direction for understanding metalloenzymes and designing new biomimetic catalysts.
• Synthesis of a series of novel N,N-dialkyl-TsDPEN ligands and their application to enantioselective addition of dialkylzinc to benzaldehyde
  作者：José E.D. Martins、Martin Wills

  DOI：10.1016/j.tetasy.2008.04.020

  日期：2008.5

  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.
• Application of Ruthenium Complexes of Triazole-Containing Tridentate Ligands to Asymmetric Transfer Hydrogenation of Ketones
  作者：Tarn C. Johnson、William G. Totty、Martin Wills

  DOI：10.1021/ol302354z

  日期：2012.10.19

  The synthesis of a series of tridentate ligands based on a homochiral 1,2-diamine structure attached to a triazole group and their subsequent applications to the asymmetric transfer hydrogenation of ketones are described. In the best cases, alcohols of up to 93% ee were obtained. Although base is not required, the use of Ru3(CO)12 as metal source is essential, indicating a unique mechanism for the

  描述了基于与三唑基连接的同手性1,2-二胺结构的一系列三齿配体的合成及其在酮的不对称转移氢化中的后续应用。在最佳情况下，获得的酒精含量高达ee的93％。尽管不需要碱，但是必须使用Ru 3（CO）12作为金属源，这表明形成活性催化剂的独特机理。