4-hydroxy-3-(2-propenyl)-2',6'-dinitrobiphenyl | 129001-64-5

• 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: 4-hydroxy-3-(2-propenyl)-2',6'-dinitrobiphenyl
• 英文别名: 3-allyl-4-hydroxy-2',6'-dinitrobiphenyl；4-(2,6-dinitrophenyl)-2-prop-2-enylphenol
• CAS: 129001-64-5
• 化学式: C₁₅H₁₂N₂O₅
• 分子量: 300.271
• InChiKey: FRBWNFPSTGLFCX-UHFFFAOYSA-N

物化性质

• 沸点：
  428.9±40.0 °C(predicted)
• 密度：
  1.357±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  106.51
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(2-propenyl)-2',6'-dinitrobiphenyl 在 吡啶 、 2,3,5-三甲基吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 双氧水 、 sodium 、 三氯化硼 、 铁粉 、 potassium carbonate 、 氯化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 76.0h， 生成 4-(benzyloxy)-3,5-bis(3-bromopropyl)-2',6'-bis(6-bromohexanamido)biphenyl
  参考文献：
  名称：

  Pendant-capped porphyrins. 1. The synthesis of a biphenyl pendant-capped iron(III) porphyrin model of catalase

  摘要：

  A phenol pendant-capped porphyrin ((PHPCP)H2) and its iron(III) complex ((PPCP)Fe(III)) have been synthesized. H-1 and C-13 NMR were used to characterize all intermediates leading to the final product. In addition, the heteronuclear C-13-H-1 shift correlation experiment was used to further characterize the tetraaldehyde precursor of the pendant-capped porphyrin. Proton and carbon chemical shifts for the free base porphyrin (PHPCP)H2 were assigned by using one-dimensional NMR experiments (including C-13 APT) and two-dimensional homonuclear COSY and ROESY experiments. In (PHPCP)H2, the phenol that provides the ligand is hung from the ceiling of a vaulted dome or tepee with protected walls supported by four legs that are anchored to the 2-position of the phenyl rings at the 5,10,15,20-meso-carbons of (TPP)H2. In the ground-state structure of (PPCP)Fe(III), the phenol is dissociated such that the resultant phenolate species is ligated to the high-spin (S = 5/2) iron(III). Ligation of phenolate and iron moieties is established by (i) comparison of H-1 NMR to the H-1 NMR of the phenolate complex of [(TPP)Fe(III)]+; (ii) comparison of the UV/vis spectrum to that for the phenolate complex of [(TPP)Fe(III)]+; (iii) disappearance of the O-H stretch in the IR accompanying complexation of (PHPCP)H2 with Fe(III); and (iv) laser desorption mass spectroscopy. At the active site of catalase, the protoporphyrin-IX iron(III) is ligated to the phenolate form of a tyrosine residue.

  DOI：

  10.1021/ja00021a042
• 作为产物：
  描述：

  4-methoxy-2',6'-dinitrobiphenyl 在 sodium 、 三氯化硼 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 、 氯苯 为溶剂， 反应 26.7h， 生成 4-hydroxy-3-(2-propenyl)-2',6'-dinitrobiphenyl
  参考文献：
  名称：

  Pendant-capped porphyrins. 1. The synthesis of a biphenyl pendant-capped iron(III) porphyrin model of catalase

  摘要：

  A phenol pendant-capped porphyrin ((PHPCP)H2) and its iron(III) complex ((PPCP)Fe(III)) have been synthesized. H-1 and C-13 NMR were used to characterize all intermediates leading to the final product. In addition, the heteronuclear C-13-H-1 shift correlation experiment was used to further characterize the tetraaldehyde precursor of the pendant-capped porphyrin. Proton and carbon chemical shifts for the free base porphyrin (PHPCP)H2 were assigned by using one-dimensional NMR experiments (including C-13 APT) and two-dimensional homonuclear COSY and ROESY experiments. In (PHPCP)H2, the phenol that provides the ligand is hung from the ceiling of a vaulted dome or tepee with protected walls supported by four legs that are anchored to the 2-position of the phenyl rings at the 5,10,15,20-meso-carbons of (TPP)H2. In the ground-state structure of (PPCP)Fe(III), the phenol is dissociated such that the resultant phenolate species is ligated to the high-spin (S = 5/2) iron(III). Ligation of phenolate and iron moieties is established by (i) comparison of H-1 NMR to the H-1 NMR of the phenolate complex of [(TPP)Fe(III)]+; (ii) comparison of the UV/vis spectrum to that for the phenolate complex of [(TPP)Fe(III)]+; (iii) disappearance of the O-H stretch in the IR accompanying complexation of (PHPCP)H2 with Fe(III); and (iv) laser desorption mass spectroscopy. At the active site of catalase, the protoporphyrin-IX iron(III) is ligated to the phenolate form of a tyrosine residue.

  DOI：

  10.1021/ja00021a042

文献信息

• First synthesis of a pendant-capped porphyrin. A biphenyl pendant-capped porphyrin model of catalase
  作者：Chang Hee Lee、Barbara Garcia、Thomas C. Bruice

  DOI：10.1021/ja00173a062

  日期：1990.8