cyanomethyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate | 1533429-83-2

• 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: cyanomethyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate
• 英文别名: cyanomethyl (2S)-2-[(4,5-dimethoxy-2-nitrophenyl)methoxycarbonylamino]-3-(1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate
• CAS: 1533429-83-2
• 化学式: C₂₆H₂₃N₅O₈
• 分子量: 533.497
• InChiKey: YMNMIZQOSPQVHI-IBGZPJMESA-N

物化性质

• 沸点：
  841.8±65.0 °C(predicted)
• 密度：
  1.423±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  cyanomethyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate 、 phosphoro-2′-deoxycytidylyl[3′→5′]adenosine tris(tetrabutylammonium) salt 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以52%的产率得到(S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1H-pyrrolo[3,2-c]isoquinolin-3-yl)-pdCpA
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Tryptophan Analogues Having Useful Photophysical Properties

  摘要：

  Two new fluorescent probes of protein structure and dynamics have been prepared by concise asymmetric syntheses using the Schollkopf chiral auxiliary. The site-specific incorporation of one probe into dihydrofolate reductase is reported. The utility of these tryptophan derivatives lies in their absorption and emission maxima which differ from those of tryptophan, as well as in their large Stokes shifts and high molar absorptivities.

  DOI：

  10.1021/ol403429e
• 作为产物：
  描述：

  4-溴异喹啉 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 sodium tetrahydroborate 、 copper(l) iodide 、 正丁基锂 、 氯化亚砜 、 乌洛托品 、 碘 、 铜 、 sodium hydride 、 potassium carbonate 、 caesium carbonate 、 silver sulfate 、 sodium amide 、 三乙胺 、 copper(l) chloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 103.67h， 生成 cyanomethyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Tryptophan Analogues Having Useful Photophysical Properties

  摘要：

  Two new fluorescent probes of protein structure and dynamics have been prepared by concise asymmetric syntheses using the Schollkopf chiral auxiliary. The site-specific incorporation of one probe into dihydrofolate reductase is reported. The utility of these tryptophan derivatives lies in their absorption and emission maxima which differ from those of tryptophan, as well as in their large Stokes shifts and high molar absorptivities.

  DOI：

  10.1021/ol403429e

文献信息

• Efficient Asymmetric Synthesis of Tryptophan Analogues Having Useful Photophysical Properties
  作者：Poulami Talukder、Shengxi Chen、Pablo M. Arce、Sidney M. Hecht

  DOI：10.1021/ol403429e

  日期：2014.1.17

  Two new fluorescent probes of protein structure and dynamics have been prepared by concise asymmetric syntheses using the Schollkopf chiral auxiliary. The site-specific incorporation of one probe into dihydrofolate reductase is reported. The utility of these tryptophan derivatives lies in their absorption and emission maxima which differ from those of tryptophan, as well as in their large Stokes shifts and high molar absorptivities.