(S)-N-2-chloroethanoyl-(4-cyanophenyl)ethylamine | 222714-30-9

• 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)-N-2-chloroethanoyl-(4-cyanophenyl)ethylamine
• 英文别名: 2-chloro-N-[(1S)-1-(4-cyanophenyl)ethyl]acetamide
• CAS: 222714-30-9
• 化学式: C₁₁H₁₁ClN₂O
• 分子量: 222.674
• InChiKey: SCFDQSHVUBJKFE-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  轮环藤宁 、 (S)-N-2-chloroethanoyl-(4-cyanophenyl)ethylamine 在 caesium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1,4,7,10-tetrakis<(S)-1-(4-cyanophenyl)ethylcarbamoylmethyl>-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Synthesis, Time-Resolved Luminescence, NMR Spectroscopy, Circular Dichroism and Circularly Polarised Luminescence Studies of Enantiopure Macrocyclic Lanthanide Tetraamide Complexes

  摘要：

  The syntheses and properties of a series of lanthanide complexes (Ln = Eu, Tb, Dy, Yb) of C-4 symmetric chiral tetraamide ligands based on 1,4,7,10-tetraazacyclododecane are reported. The configuration of the chiral centre at carbon in the amide substituent (CH2NHCO-CH(Me)Ar) determines the helicity of the derived complex and the configuration of the macrocyclic ring. The enantiopure lanthanide complexes do not undergo Delta/Lambda interconversion in the temperature range 220 to 320 K and three complexes have been characterised by X-ray crystallography, revealing nine-coordination about the lanthanide ion (Ln=Eu, Dy) with a monocapped square-antiprismatic coordination geometry. The terbium complexes are highly emissive in aqueous solution following excitation into the aryl chromophore (e.g. for [Tb .(R)-7a](3+) phi H2O = 0.49; phi D2O = 0.81) and all of the lanthanide complexes exhibit strong circularly polarised luminescence. The ytterbium complexes (e.g. [Yb .(S)-5b](3+)) shows a strong near-IR CD and circularly polarised luminescence (CPL) associated with the F-2(5/2)-F-2(7/2) transition. Overall, these emissive complexes allow control in modulating both the frequency and the polarisation of emitted light in aqueous solution.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<1095::aid-chem1095>3.0.co;2-c
• 作为产物：
  描述：

  (S)-N-乙酰-1-(4-溴苯基)乙胺 在 盐酸 、 水 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 (S)-N-2-chloroethanoyl-(4-cyanophenyl)ethylamine
  参考文献：
  名称：

  Synthesis, Time-Resolved Luminescence, NMR Spectroscopy, Circular Dichroism and Circularly Polarised Luminescence Studies of Enantiopure Macrocyclic Lanthanide Tetraamide Complexes

  摘要：

  The syntheses and properties of a series of lanthanide complexes (Ln = Eu, Tb, Dy, Yb) of C-4 symmetric chiral tetraamide ligands based on 1,4,7,10-tetraazacyclododecane are reported. The configuration of the chiral centre at carbon in the amide substituent (CH2NHCO-CH(Me)Ar) determines the helicity of the derived complex and the configuration of the macrocyclic ring. The enantiopure lanthanide complexes do not undergo Delta/Lambda interconversion in the temperature range 220 to 320 K and three complexes have been characterised by X-ray crystallography, revealing nine-coordination about the lanthanide ion (Ln=Eu, Dy) with a monocapped square-antiprismatic coordination geometry. The terbium complexes are highly emissive in aqueous solution following excitation into the aryl chromophore (e.g. for [Tb .(R)-7a](3+) phi H2O = 0.49; phi D2O = 0.81) and all of the lanthanide complexes exhibit strong circularly polarised luminescence. The ytterbium complexes (e.g. [Yb .(S)-5b](3+)) shows a strong near-IR CD and circularly polarised luminescence (CPL) associated with the F-2(5/2)-F-2(7/2) transition. Overall, these emissive complexes allow control in modulating both the frequency and the polarisation of emitted light in aqueous solution.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<1095::aid-chem1095>3.0.co;2-c

文献信息

• Synthesis, Time-Resolved Luminescence, NMR Spectroscopy, Circular Dichroism and Circularly Polarised Luminescence Studies of Enantiopure Macrocyclic Lanthanide Tetraamide Complexes
  作者：Rachel S. Dickins、Judith A. K. Howard、Christine L. Maupin、Janet M. Moloney、David Parker、James P. Riehl、Giuliano Siligardi、J. A. Gareth Williams

  DOI：10.1002/(sici)1521-3765(19990301)5:3<1095::aid-chem1095>3.0.co;2-c

  日期：1999.3.1

  The syntheses and properties of a series of lanthanide complexes (Ln = Eu, Tb, Dy, Yb) of C-4 symmetric chiral tetraamide ligands based on 1,4,7,10-tetraazacyclododecane are reported. The configuration of the chiral centre at carbon in the amide substituent (CH2NHCO-CH(Me)Ar) determines the helicity of the derived complex and the configuration of the macrocyclic ring. The enantiopure lanthanide complexes do not undergo Delta/Lambda interconversion in the temperature range 220 to 320 K and three complexes have been characterised by X-ray crystallography, revealing nine-coordination about the lanthanide ion (Ln=Eu, Dy) with a monocapped square-antiprismatic coordination geometry. The terbium complexes are highly emissive in aqueous solution following excitation into the aryl chromophore (e.g. for [Tb .(R)-7a](3+) phi H2O = 0.49; phi D2O = 0.81) and all of the lanthanide complexes exhibit strong circularly polarised luminescence. The ytterbium complexes (e.g. [Yb .(S)-5b](3+)) shows a strong near-IR CD and circularly polarised luminescence (CPL) associated with the F-2(5/2)-F-2(7/2) transition. Overall, these emissive complexes allow control in modulating both the frequency and the polarisation of emitted light in aqueous solution.