tert-butyl N-[3-[(4-tert-butylphenyl)methyl-[2-(1,3-dioxoisoindol-2-yl)benzoyl]amino]phenyl]carbamate | 199171-70-5

• 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: tert-butyl N-[3-[(4-tert-butylphenyl)methyl-[2-(1,3-dioxoisoindol-2-yl)benzoyl]amino]phenyl]carbamate
• CAS: 199171-70-5
• 化学式: C₃₇H₃₇N₃O₅
• 分子量: 603.718
• InChiKey: GXSHOOZCZNFBSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[3-[(4-tert-butylphenyl)methyl-[2-(1,3-dioxoisoindol-2-yl)benzoyl]amino]phenyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到N-(3-aminophenyl)-N-[(4-tert-butylphenyl)methyl]-2-(1,3-dioxoisoindol-2-yl)benzamide
  参考文献：
  名称：

  Self-Assembly of Zinc Porphyrins around the Periphery of Hydrogen-Bonded Aggregates That Bear Imidazole Groups

  摘要：

  This paper describes the preparation and characterization of four aggregates that are based an the rosette of derivatives of isocyanuric acid (CA) and melamine (M). These aggregates comprise a trismelamine, hub(M-Im)(3), that presents imidazole groups around its periphery; these imidazoles organize zinc tetraphenyl porphyrin (ZnTPP) by coordination of the imidazole to the zinc center. Aggregate 1 forms a single rosette upon mixing 1 equiv of hub(M-Im)(3) and 3 equiv of CA. Adding 3 equiv of ZnTPP yields 2. Aggregate 3 forms as a stacked bisrosette upon mixing 2 equiv of hub(M-Im)(3) and 3 equiv of bisCA. Adding 6 equiv of ZnTPP yields 4. The stoichiometries of aggregates 1-4 were obtained by titrating the trismelamines with CA and by titrating the aggregates with ZnTPP. The stoichiometry is defined as the ratio at which additional CA remains insoluble or additional ZnTPP appears as free ZnTPP in the H-1 NMR spectrum. Electrospray ionization mass spectrometry (ESI-MS) is compatible with the measured stoichiometries, The structures of these aggregates were determined using variable-temperature H-1 NMR spectroscopy;analogous structures were inferred for 5 and 6, the tert-butyl analogues of 1 and 2. The shapes of the traces from gel permeation chromatography (GPC) suggest that imidazole groups destabilize the aggregates when they are not involved in coordination to zinc; that is, the stability seems to be 6 approximate to 4 > 3 and 5 approximate to 2 > 1. A direct comparison of the relative stability of 1, 2, and 5 confirms the results of the GPC analysis: mixing 1 (hub(M-IM)(3).3CA) with the trismelamine component of 5 (hub(M)(3)) leads to the formation of a 3:2 mixture of 5:1. Adding ZnTPP to this solution leads to a 3:2 mixture of 5:2 with free trismelamines remaining in solution: 1 is not observed, The results of UV/vis spectroscopy are consistent with the other spectroscopic and chromatographic results and indicate that 3 equiv of ZnTPP are organized around the periphery of 2 and at least 4 equiv around the periphery of 4.

  DOI：

  10.1021/jo9615458
• 作为产物：
  描述：

  邻苯二甲酰氯 在 氯化亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 生成 tert-butyl N-[3-[(4-tert-butylphenyl)methyl-[2-(1,3-dioxoisoindol-2-yl)benzoyl]amino]phenyl]carbamate
  参考文献：
  名称：

  Self-Assembly of Zinc Porphyrins around the Periphery of Hydrogen-Bonded Aggregates That Bear Imidazole Groups

  摘要：

  This paper describes the preparation and characterization of four aggregates that are based an the rosette of derivatives of isocyanuric acid (CA) and melamine (M). These aggregates comprise a trismelamine, hub(M-Im)(3), that presents imidazole groups around its periphery; these imidazoles organize zinc tetraphenyl porphyrin (ZnTPP) by coordination of the imidazole to the zinc center. Aggregate 1 forms a single rosette upon mixing 1 equiv of hub(M-Im)(3) and 3 equiv of CA. Adding 3 equiv of ZnTPP yields 2. Aggregate 3 forms as a stacked bisrosette upon mixing 2 equiv of hub(M-Im)(3) and 3 equiv of bisCA. Adding 6 equiv of ZnTPP yields 4. The stoichiometries of aggregates 1-4 were obtained by titrating the trismelamines with CA and by titrating the aggregates with ZnTPP. The stoichiometry is defined as the ratio at which additional CA remains insoluble or additional ZnTPP appears as free ZnTPP in the H-1 NMR spectrum. Electrospray ionization mass spectrometry (ESI-MS) is compatible with the measured stoichiometries, The structures of these aggregates were determined using variable-temperature H-1 NMR spectroscopy;analogous structures were inferred for 5 and 6, the tert-butyl analogues of 1 and 2. The shapes of the traces from gel permeation chromatography (GPC) suggest that imidazole groups destabilize the aggregates when they are not involved in coordination to zinc; that is, the stability seems to be 6 approximate to 4 > 3 and 5 approximate to 2 > 1. A direct comparison of the relative stability of 1, 2, and 5 confirms the results of the GPC analysis: mixing 1 (hub(M-IM)(3).3CA) with the trismelamine component of 5 (hub(M)(3)) leads to the formation of a 3:2 mixture of 5:1. Adding ZnTPP to this solution leads to a 3:2 mixture of 5:2 with free trismelamines remaining in solution: 1 is not observed, The results of UV/vis spectroscopy are consistent with the other spectroscopic and chromatographic results and indicate that 3 equiv of ZnTPP are organized around the periphery of 2 and at least 4 equiv around the periphery of 4.

  DOI：

  10.1021/jo9615458

文献信息

• Self-Assembly of Zinc Porphyrins around the Periphery of Hydrogen-Bonded Aggregates That Bear Imidazole Groups
  作者：Eric E. Simanek、Lyle Isaacs、Xinhua Li、Clay C. C. Wang、George M. Whitesides

  DOI：10.1021/jo9615458

  日期：1997.12.1

  This paper describes the preparation and characterization of four aggregates that are based an the rosette of derivatives of isocyanuric acid (CA) and melamine (M). These aggregates comprise a trismelamine, hub(M-Im)(3), that presents imidazole groups around its periphery; these imidazoles organize zinc tetraphenyl porphyrin (ZnTPP) by coordination of the imidazole to the zinc center. Aggregate 1 forms a single rosette upon mixing 1 equiv of hub(M-Im)(3) and 3 equiv of CA. Adding 3 equiv of ZnTPP yields 2. Aggregate 3 forms as a stacked bisrosette upon mixing 2 equiv of hub(M-Im)(3) and 3 equiv of bisCA. Adding 6 equiv of ZnTPP yields 4. The stoichiometries of aggregates 1-4 were obtained by titrating the trismelamines with CA and by titrating the aggregates with ZnTPP. The stoichiometry is defined as the ratio at which additional CA remains insoluble or additional ZnTPP appears as free ZnTPP in the H-1 NMR spectrum. Electrospray ionization mass spectrometry (ESI-MS) is compatible with the measured stoichiometries, The structures of these aggregates were determined using variable-temperature H-1 NMR spectroscopy;analogous structures were inferred for 5 and 6, the tert-butyl analogues of 1 and 2. The shapes of the traces from gel permeation chromatography (GPC) suggest that imidazole groups destabilize the aggregates when they are not involved in coordination to zinc; that is, the stability seems to be 6 approximate to 4 > 3 and 5 approximate to 2 > 1. A direct comparison of the relative stability of 1, 2, and 5 confirms the results of the GPC analysis: mixing 1 (hub(M-IM)(3).3CA) with the trismelamine component of 5 (hub(M)(3)) leads to the formation of a 3:2 mixture of 5:1. Adding ZnTPP to this solution leads to a 3:2 mixture of 5:2 with free trismelamines remaining in solution: 1 is not observed, The results of UV/vis spectroscopy are consistent with the other spectroscopic and chromatographic results and indicate that 3 equiv of ZnTPP are organized around the periphery of 2 and at least 4 equiv around the periphery of 4.