(R,R)-N-acetyl-N'-TsDPEN | 1043450-09-4

• 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-acetyl-N'-TsDPEN
• 英文别名: (1R,2R)-N-[1,2-diphenyl-2-(toluene-4-sulfonylamino)-ethyl]acetamide；N-((1R,2R)-2-((4-methylphenyl)sulfonamido)-1,2-diphenylethyl)acetamide
• CAS: 1043450-09-4
• 化学式: C₂₃H₂₄N₂O₃S
• 分子量: 408.521
• InChiKey: DKGTUBCUQXRVAE-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R,R)-N-acetyl-N'-TsDPEN 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以75%的产率得到(1R,2R)-N-(2-ethylamino-1,2-diphenyl-ethyl)-4-methyl-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
• 作为产物：
  描述：

  乙酰氯 、 (1R,2R)-(-)-N-(对甲基苯磺酰基)-1,2-二苯基乙二胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(R,R)-N-acetyl-N'-TsDPEN
  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

• Direct β‐ and γ‐C(sp ³ )−H Alkynylation of Free Carboxylic Acids**
  作者：Francesca Ghiringhelli、Alexander Uttry、Kiron Kumar Ghosh、Manuel Gemmeren

  DOI：10.1002/anie.202010784

  日期：2020.12.14

  palladium‐catalyzed C(sp3)−H activation that enables the direct alkynylation of free carboxylic acid substrates. In contrast to previous synthetic methods, no introduction/removal of an exogenous directing group is required. A broad scope of acids including both α‐quaternary and challenging α‐non‐quaternary can be used as substrates. Additionally, the alkynylation in the distal γ‐position is reported. Finally

  在这项研究中，我们报告了一种用于钯催化 C(sp 3 )−H 活化的新型配体的鉴定，该配体能够实现游离羧酸底物的直接炔基化。与以前的合成方法相比，不需要引入/去除外源导向基团。多种酸（包括 α-季铵盐和具有挑战性的 α-非季铵盐）均可用作底物。此外，还报道了远端 γ 位的炔基化。最后，本研究涵盖了标题转换的对映选择性变体的初步发现以及所获得产品的合成应用。
• 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.