L-2-(benzhydrylidene-amino)-N-{2-[2-(benzhydrylidene-amino)-3-phenyl-propionylamino]-phenyl}-3-phenyl-propionamide | 197431-88-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-2-(benzhydrylidene-amino)-N-{2-[2-(benzhydrylidene-amino)-3-phenyl-propionylamino]-phenyl}-3-phenyl-propionamide
• 英文别名: (2S)-2-(benzhydrylideneamino)-N-[2-[[(2S)-2-(benzhydrylideneamino)-3-phenylpropanoyl]amino]phenyl]-3-phenylpropanamide
• CAS: 197431-88-2
• 化学式: C₅₀H₄₂N₄O₂
• 分子量: 730.909
• InChiKey: JXCFCKOVSFQOLP-ZYBCLOSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethylzinc 、 L-2-(benzhydrylidene-amino)-N-{2-[2-(benzhydrylidene-amino)-3-phenyl-propionylamino]-phenyl}-3-phenyl-propionamide 以 四氢呋喃 为溶剂， 以90%的产率得到2(S)-(benzhydrylidene-amino)-N-(2-[2(S)-(benzhydrylidene-amino)-3-phenyl-propionylamino]-phenyl)-3-phenyl-propionamide-zinc(II) complex
  参考文献：
  名称：

  Optically Active 4- and 5-Coordinate Transition Metal Complexes of Bifurcated Dipeptide Schiff Bases

  摘要：

  Symmetrical and unsymmetrical benzophenone Schiff bases of bifurcated dipeptides [e.g., Ar2C=N-CHR1-CONHsimilar toHNCO-CHR2-N=CAr2] have been synthesized using Boc methodology. These ligands may be regarded as chiral porphyrin mimics because of the a-carbons of the amino acids. The Schiff bases function as effective ligands for transition metals, particularly the late transition metals Ni(II), Cu(II), and Zn. Upon metal insertion, there is loss of the amide protons, resulting in N-4 chelating ligands that retain the amino acid based chirality as well as newly generated metal-centered chirality, which for the Ni(II) complexes have been shown by X-ray analysis to be A (left-handed helix) if the amino acids are S. For Ni(II) and Cu(II), metal insertion results in highly colored complexes and is easily followed by UV-vis spectrophotometry. Several Ni(II) complexes were also characterized by H-1 NMR. Co(II) and Mn(II) complexes were characterized by CW EPR. Two Cu(II) complexes, 7f.Cu-II and 7k.Cu-II, were characterized by EPR (ENDOR and ESEEM), which clearly showed the pentacoordinate nature of 7k.Cu-II.

  DOI：

  10.1021/ic025996o
• 作为产物：
  描述：

  L-{1-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-phenylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 在 甲醇 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 L-2-(benzhydrylidene-amino)-N-{2-[2-(benzhydrylidene-amino)-3-phenyl-propionylamino]-phenyl}-3-phenyl-propionamide
  参考文献：
  名称：

  氨基酸衍生的四配位络合物的催化作用：将二烷基锌对映选择性地添加到脂肪族和芳香族醛中。

  摘要：

  在3摩尔％的2存在下，将Me（2）Zn和Et（2）Zn添加到芳族和脂族醛中。（S）-1-苯基乙醇（91％ee）和（S）-1-苯基丙醇（86％） ee）由苯甲醛合成，（S）-1-呋喃-2-基-1-丙醇（86％ee）由2-呋喃甲醛合成。壬醛和3-苯基丙醛提供（S）-3-十一烷醇（96％ee）和（S）-1-苯基-3-戊醇（94％ee）。固相变体对于（S）-1-苯基丙醇具有降低的ee（例如86％ee-> 79％ee）有效。

  DOI：

  10.1021/ol0063151

文献信息

• Amino Acid-Derived Ligands for Transition Metals:  Catalysis via a Minimalist Interpretation of a Metalloprotein
  作者：Brian Dangel、Michael Clarke、Jay Haley、Dalibor Sames、Robin Polt

  DOI：10.1021/ja972135j

  日期：1997.11.1
• Catalysis by Amino Acid-Derived Tetracoordinate Complexes:  Enantioselective Addition of Dialkylzincs to Aliphatic and Aromatic Aldehydes
  作者：Brian D. Dangel、Robin Polt

  DOI：10.1021/ol0063151

  日期：2000.9.1

  Me(2)Zn and Et(2)Zn added to aromatic and aliphatic aldehydes in the presence of 3 mol % of 2. (S)-1-Phenylethanol (91% ee) and (S)-1-phenylpropanol (86% ee) were synthesized from benzaldehyde and (S)-1-furan-2-yl-1-propanol (86% ee) from 2-furaldehyde. Nonanal and 3-phenylpropanal provided (S)-3-undecanol (96% ee) and (S)-1-phenyl-3-pentanol (94% ee). A solid-phase variant was effective with reduced

  在3摩尔％的2存在下，将Me（2）Zn和Et（2）Zn添加到芳族和脂族醛中。（S）-1-苯基乙醇（91％ee）和（S）-1-苯基丙醇（86％） ee）由苯甲醛合成，（S）-1-呋喃-2-基-1-丙醇（86％ee）由2-呋喃甲醛合成。壬醛和3-苯基丙醛提供（S）-3-十一烷醇（96％ee）和（S）-1-苯基-3-戊醇（94％ee）。固相变体对于（S）-1-苯基丙醇具有降低的ee（例如86％ee-> 79％ee）有效。
• Optically Active 4- and 5-Coordinate Transition Metal Complexes of Bifurcated Dipeptide Schiff Bases
  作者：Robin Polt、Brian D. Kelly、Brian D. Dangel、Udaya Bhaskar Tadikonda、Regina E. Ross、Arnold M. Raitsimring、Andrei V. Astashkin

  DOI：10.1021/ic025996o

  日期：2003.1.1

  Symmetrical and unsymmetrical benzophenone Schiff bases of bifurcated dipeptides [e.g., Ar2C=N-CHR1-CONHsimilar toHNCO-CHR2-N=CAr2] have been synthesized using Boc methodology. These ligands may be regarded as chiral porphyrin mimics because of the a-carbons of the amino acids. The Schiff bases function as effective ligands for transition metals, particularly the late transition metals Ni(II), Cu(II), and Zn. Upon metal insertion, there is loss of the amide protons, resulting in N-4 chelating ligands that retain the amino acid based chirality as well as newly generated metal-centered chirality, which for the Ni(II) complexes have been shown by X-ray analysis to be A (left-handed helix) if the amino acids are S. For Ni(II) and Cu(II), metal insertion results in highly colored complexes and is easily followed by UV-vis spectrophotometry. Several Ni(II) complexes were also characterized by H-1 NMR. Co(II) and Mn(II) complexes were characterized by CW EPR. Two Cu(II) complexes, 7f.Cu-II and 7k.Cu-II, were characterized by EPR (ENDOR and ESEEM), which clearly showed the pentacoordinate nature of 7k.Cu-II.