9H-fluoren-9-ylmethyl N-[(4-bromophenyl)methyl]carbamate | 914659-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-[(4-bromophenyl)methyl]carbamate
• CAS: 914659-42-0
• 化学式: C₂₂H₁₈BrNO₂
• 分子量: 408.294
• InChiKey: HJRKUKNJBIWZCS-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  576.9±38.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-[(4-bromophenyl)methyl]carbamate 在 四(三苯基膦)钯 sodium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 36.0h， 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：

  氯甲酸-9-芴基甲酯 、 4-溴苄胺盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到9H-fluoren-9-ylmethyl N-[(4-bromophenyl)methyl]carbamate
  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