4-(4-nitrosophenyl)-benzoic acid tert-butyl ester | 914659-79-3

• 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-(4-nitrosophenyl)-benzoic acid tert-butyl ester
• 英文别名: Tert-butyl 4-(4-nitrosophenyl)benzoate
• CAS: 914659-79-3
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: TVLPQVJIJHQMJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-nitrosophenyl)-benzoic acid tert-butyl ester 、 (4'-Amino-biphenyl-4-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 在 溶剂黄146 作用下， 反应 24.0h， 生成 、
  参考文献：
  名称：

  Abc Amino Acids:  Design, Synthesis, and Properties of New Photoelastic Amino Acids

  摘要：

  Photoisomerizable amino acids provide a direct avenue to the experimental manipulation of bioactive polypeptides, potentially allowing real-time, remote control of biological systems and enabling useful applications in nanobiotechnology. Herein, we report a new class of photoisomerizable amino acids intended to cause pronounced expansion and contraction in the polypeptide backbone, i.e., to be photoelastic. These compounds, termed Abc amino acids, employ a photoisomerizable azobiphenyl chromophore to control the relative disposition of aminomethyl and carboxyl substituents. Molecular modeling of nine Abc isomers led to the identification of one with particularly attractive properties, including the ability to induce contractions up to 13 angstrom in the backbone upon trans -> cis photoisomerization. This isomer, designated mpAbc, has substituents at meta and para positions on the inner (azolinked) and outer rings, respectively. An efficient synthesis of Fmoc-protected mpAbc was executed in which the biaryl components were formed via Suzuki couplings and the azo linkage was formed via amine/nitroso condensation; protected forms of three other Abc isomers were prepared similarly. An undecapeptide incorporating mpAbc was synthesized by conventional solid-phase methods and displayed characteristic azobenzene photochemical behavior with optimal conversion to the cis isomer at 360 nm and a thermal cis -> trans half-life of 100 min at 80 degrees C.

  DOI：

  10.1021/jo060763q
• 作为产物：
  描述：

  4-羧基苯硼酸 在 四(三苯基膦)钯 硫酸 、 三氯化铁 、 sodium carbonate 、 氯化铵 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 乙二醇甲醚 、 水 、 甲苯 为溶剂， 反应 40.0h， 生成 4-(4-nitrosophenyl)-benzoic acid tert-butyl ester
  参考文献：
  名称：

  Abc Amino Acids:  Design, Synthesis, and Properties of New Photoelastic Amino Acids

  摘要：

  Photoisomerizable amino acids provide a direct avenue to the experimental manipulation of bioactive polypeptides, potentially allowing real-time, remote control of biological systems and enabling useful applications in nanobiotechnology. Herein, we report a new class of photoisomerizable amino acids intended to cause pronounced expansion and contraction in the polypeptide backbone, i.e., to be photoelastic. These compounds, termed Abc amino acids, employ a photoisomerizable azobiphenyl chromophore to control the relative disposition of aminomethyl and carboxyl substituents. Molecular modeling of nine Abc isomers led to the identification of one with particularly attractive properties, including the ability to induce contractions up to 13 angstrom in the backbone upon trans -> cis photoisomerization. This isomer, designated mpAbc, has substituents at meta and para positions on the inner (azolinked) and outer rings, respectively. An efficient synthesis of Fmoc-protected mpAbc was executed in which the biaryl components were formed via Suzuki couplings and the azo linkage was formed via amine/nitroso condensation; protected forms of three other Abc isomers were prepared similarly. An undecapeptide incorporating mpAbc was synthesized by conventional solid-phase methods and displayed characteristic azobenzene photochemical behavior with optimal conversion to the cis isomer at 360 nm and a thermal cis -> trans half-life of 100 min at 80 degrees C.

  DOI：

  10.1021/jo060763q

文献信息

• Abc Amino Acids:  Design, Synthesis, and Properties of New Photoelastic Amino Acids
  作者：Robert F. Standaert、Seung Bum Park

  DOI：10.1021/jo060763q

  日期：2006.10.1

  Photoisomerizable amino acids provide a direct avenue to the experimental manipulation of bioactive polypeptides, potentially allowing real-time, remote control of biological systems and enabling useful applications in nanobiotechnology. Herein, we report a new class of photoisomerizable amino acids intended to cause pronounced expansion and contraction in the polypeptide backbone, i.e., to be photoelastic. These compounds, termed Abc amino acids, employ a photoisomerizable azobiphenyl chromophore to control the relative disposition of aminomethyl and carboxyl substituents. Molecular modeling of nine Abc isomers led to the identification of one with particularly attractive properties, including the ability to induce contractions up to 13 angstrom in the backbone upon trans -> cis photoisomerization. This isomer, designated mpAbc, has substituents at meta and para positions on the inner (azolinked) and outer rings, respectively. An efficient synthesis of Fmoc-protected mpAbc was executed in which the biaryl components were formed via Suzuki couplings and the azo linkage was formed via amine/nitroso condensation; protected forms of three other Abc isomers were prepared similarly. An undecapeptide incorporating mpAbc was synthesized by conventional solid-phase methods and displayed characteristic azobenzene photochemical behavior with optimal conversion to the cis isomer at 360 nm and a thermal cis -> trans half-life of 100 min at 80 degrees C.