(S)-N¹,N²-dibenzyl-3-phenylpropane-1,2-diamine | 1229703-73-4

• 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: (S)-N¹,N²-dibenzyl-3-phenylpropane-1,2-diamine
• 英文别名: (2S)-1-N,2-N-dibenzyl-3-phenylpropane-1,2-diamine
• CAS: 1229703-73-4
• 化学式: C₂₃H₂₆N₂
• 分子量: 330.473
• InChiKey: FUIJAGLFBVWIAM-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N¹,N²-dibenzyl-3-phenylpropane-1,2-diamine 、 原甲酸三乙酯 在 ammonium tetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以95%的产率得到(S)-1,3,4-tribenzyl-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate
  参考文献：
  名称：

  Chiral relay in NHC-mediated asymmetric β-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines

  摘要：

  The synthesis of a range of imidazolinium salts derived from acyclic 1,2-diamines, and an evaluation of the reactivity and asymmetric induction of the corresponding NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. An N-methyl-substituted NHC derived from (1R,2R)-1,2-diphenylethanediamine shows optimal reactivity and enantioselectivity in this series, in contrast to that observed with NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.002
• 作为产物：
  描述：

  (S)-N-benzyl-2-(benzylamino)-3-phenylpropanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以51%的产率得到(S)-N¹,N²-dibenzyl-3-phenylpropane-1,2-diamine
  参考文献：
  名称：

  Chiral relay in NHC-mediated asymmetric β-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines

  摘要：

  The synthesis of a range of imidazolinium salts derived from acyclic 1,2-diamines, and an evaluation of the reactivity and asymmetric induction of the corresponding NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. An N-methyl-substituted NHC derived from (1R,2R)-1,2-diphenylethanediamine shows optimal reactivity and enantioselectivity in this series, in contrast to that observed with NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.002

文献信息

• Regioselective reductive transamination of peptidic amides enabled by a dual Zr(IV)–H catalysis
  作者：Jian-Tao Tang、Yu Gan、Xuejiao Li、Baihua Ye

  DOI：10.1016/j.chempr.2022.11.002

  日期：2022.12

  is a common structural motif of peptides and biologically active molecules, is a highly attractive target for catalytic transformations. Despite its high synthetic potential, the chemical inertness of the amide bond, owing to its resonance stabilization, has rendered this approach challenging. Existing catalytic modes essentially include metal-catalyzed carbon–nitrogen bond activation, transamidation

  酰胺基团是肽和生物活性分子的常见结构基序，是催化转化的极具吸引力的目标。尽管具有很高的合成潜力，但由于共振稳定性，酰胺键的化学惰性使这种方法具有挑战性。现有的催化方式主要包括金属催化的碳氮键活化、转酰胺基反应和催化酰胺还原。在此，我们报告了一种前所未有的催化还原转氨作用方案酰胺到交换身份的胺。通过缩醛胺的中介作用，酰胺与各种外部胺的组合会产生各种单胺和二胺，产率高，官能团相容性高，手性保留。还实现了带有多个酰胺基序的寡聚肽衍生物的区域选择性后修饰，并且实验研究和 DFT 计算都解释了位点选择性的起源。
• Chiral relay in NHC-mediated asymmetric β-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines
  作者：Nicolas Duguet、Adele Donaldson、Stuart M. Leckie、Eddy A. Kallström、Craig D. Campbell、Peter Shapland、Thomas B. Brown、Alexandra M.Z. Slawin、Andrew D. Smith

  DOI：10.1016/j.tetasy.2010.03.002

  日期：2010.3

  The synthesis of a range of imidazolinium salts derived from acyclic 1,2-diamines, and an evaluation of the reactivity and asymmetric induction of the corresponding NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. An N-methyl-substituted NHC derived from (1R,2R)-1,2-diphenylethanediamine shows optimal reactivity and enantioselectivity in this series, in contrast to that observed with NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. (C) 2010 Elsevier Ltd. All rights reserved.