4-amino-4'-aminomethylbiphenyl | 771580-90-6

• 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-amino-4'-aminomethylbiphenyl
• 英文别名: 4'-(Aminomethyl)-[1,1'-biphenyl]-4-amine；4-[4-(aminomethyl)phenyl]aniline
• CAS: 771580-90-6
• 化学式: C₁₃H₁₄N₂
• mdl: MFCD05981240
• 分子量: 198.268
• InChiKey: UVCKHZBFJDZSOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  372.1±30.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-amino-4'-aminomethylbiphenyl 、 二碳酸二叔丁酯 在 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 4-(4-氨基甲基)苯基-1-n-boc-苯胺
  参考文献：
  名称：

  在脂肪胺存在下选择性保护芳香胺的方法

  摘要：

  已经开发了一种简单有效的方法，用于在脂肪胺存在下对芳香胺进行区域选择性保护。该方法是一般为单-的制备Ñ -Boc， - Ñ -Cbz， - ñ -Fmoc或- ñ以高收率-alloc芳香胺而不影响脂族胺。该方法适用于具有不同官能度的取代的（氨基烷基）苯胺化合物，并用于提供克量的受保护的苯胺产品。 胺-氨基甲酸酯-保护基-质子化-区域选择性

  DOI：

  10.1055/s-0028-1083290
• 作为产物：
  描述：

  4-氰基-4-硝基二苯 在 氢气 、 镍 作用下， 以 甲醇 为溶剂， 生成 4-amino-4'-aminomethylbiphenyl
  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

• METHOD FOR PRODUCING BIARYL COMPOUND
  申请人：Sato Koichi

  公开号：US20100087680A1

  公开（公告）日：2010-04-08

  A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

  一种制备双芳基化合物的方法，包括在零价镍催化剂、膦配体和碱的存在下，将芳香有机化合物与选自芳香基有机硼化合物和硼氧化物化合物组的至少一种化合物反应。
• PROCESS FOR PRODUCING BIARYL COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1914221A1

  公开（公告）日：2008-04-23

  A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

  一种生产双芳基化合物的方法，包括在零价镍催化剂、膦配体和碱存在下，使芳香族有机化合物与至少一种选自由芳香族有机硼化合物和硼氧化合物组成的组中的化合物反应。
• 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.
• A Method for the Selective Protection of Aromatic Amines in the Presence of Aliphatic Amines
  作者：Boulos Zacharie、Valérie Perron、Shaun Abbott、Nancie Moreau、Devin Lee、Christopher Penney

  DOI：10.1055/s-0028-1083290

  日期：2009.1

  aromatic amines in the presence of aliphatic amines. The method is general for the preparation of mono-N-Boc, -N-Cbz, -N-Fmoc or -N-Alloc aromatic amines in high yield without affecting the aliphatic amines. This approach is applicable to substituted (aminoalkyl)aniline compounds with different functionalities and was employed to supply gram quantities of the protected aniline product. amines - carbamates

  已经开发了一种简单有效的方法，用于在脂肪胺存在下对芳香胺进行区域选择性保护。该方法是一般为单-的制备Ñ -Boc， - Ñ -Cbz， - ñ -Fmoc或- ñ以高收率-alloc芳香胺而不影响脂族胺。该方法适用于具有不同官能度的取代的（氨基烷基）苯胺化合物，并用于提供克量的受保护的苯胺产品。 胺-氨基甲酸酯-保护基-质子化-区域选择性