methyl 9-(4-bromophenyl)-2-(2-(tert-butoxycarbonylamino)ethyl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-β]indolizine-7-carboxylate | 1292323-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 9-(4-bromophenyl)-2-(2-(tert-butoxycarbonylamino)ethyl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-β]indolizine-7-carboxylate
• 英文别名: methyl 4-(4-bromophenyl)-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1-oxo-3H-pyrrolo[3,4-b]indolizine-6-carboxylate
• CAS: 1292323-69-3
• 化学式: C₂₅H₂₆BrN₃O₅
• 分子量: 528.403
• InChiKey: YUCUZUUFBNHUFF-UHFFFAOYSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  89.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(4-溴苯基)丙-2-烯-1-醇 在 sodium tetrahydroborate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium sulfate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 methyl 9-(4-bromophenyl)-2-(2-(tert-butoxycarbonylamino)ethyl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-β]indolizine-7-carboxylate
  参考文献：
  名称：

  Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one

  摘要：

  In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.

  DOI：

  10.1021/ja110766a

文献信息

• Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-<i>b</i>]indolizin-3-one
  作者：Eunha Kim、Minseob Koh、Byung Joon Lim、Seung Bum Park

  DOI：10.1021/ja110766a

  日期：2011.5.4

  In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.