biphenyl-3,3'-diyldimethanamine | 214400-72-3

• 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: biphenyl-3,3'-diyldimethanamine
• 英文别名: 3,3'-diaminomethylbiphenyl；3,3'-Bis(aminomethyl)biphenyl；[3-[3-(aminomethyl)phenyl]phenyl]methanamine
• CAS: 214400-72-3
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: RNQCFCOVAKDSAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  丁基异硫氰酸酯 、 biphenyl-3,3'-diyldimethanamine 以 氯仿 为溶剂， 反应 6.0h， 以57%的产率得到1-Butyl-3-[[3-[3-[(butylcarbamothioylamino)methyl]phenyl]phenyl]methyl]thiourea
  参考文献：
  名称：

  Novel Self-Assembly of m-Xylylene Type Dithioureas by Head-to-Tail Hydrogen Bonding

  摘要：

  Dithiourea 1a self-assembles to form an orthogonal dimer structure both in solution and in the solid state, wherein the four thiourea groups establish a closed network of hydrogen bonds through a head-to-tail binding mode. This novel dimer structure was elucidated on the basis of H-1 NMR spectra, vapor pressure osmometry, and X-ray crystal structure analysis. Furthermore, a series of m-xylylene type dithioureas were synthesized and their dimerization constants (K-a) in CDCl3 were determined by dilution experiments using H-1 NMR spectroscopy. The magnitude of the K-a values are dependent on the steric bulk of the side chains, the acidity of the thiourea groups, and the weak intermolecular interaction between the benzene rings of the side chains and the m-xylylene spacer.

  DOI：

  10.1021/jo980441p
• 作为产物：
  描述：

  3,3'-双溴甲基联苯 在 sodium azide 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 94.0h， 生成 biphenyl-3,3'-diyldimethanamine
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation of novel bivalent S-adenosylmethionine analogues

  摘要：

  In optimal cases, bivalent ligands can bind with exceptionally high affinity to their protein targets. However, designing optimised linkers, that orient the two binding groups perfectly, is challenging, and yet crucial in both fragment-based ligand design and in the discovery of bisubstrate enzyme inhibitors. To further our understanding of linker design, a series of novel bivalent S-adenosylmethionine (SAM) analogues were designed with the aim of interacting with the MetJ dimer in a bivalent sense (1:1 ligand/MetJ dimer). A range of ligands was synthesised and analyzed for ability to promote binding of the Escherichia coli methionine repressor, MetJ, to its operator DNA. Binding of bivalent SAM analogues to the MetJ homodimer in the presence of operator DNA was evaluated by fluorescence anisotropy and the effect of linker length and structure was investigated. The most effective bivalent ligand identified had a flexible linker, and promoted the DNA-protein interaction at 21-times lower concentration than the corresponding monovalent control compound. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.017

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。
• Novel Self-Assembly of <i>m</i>-Xylylene Type Dithioureas by Head-to-Tail Hydrogen Bonding
  作者：Yoshito Tobe、Shin-ichi Sasaki、Masaaki Mizuno、Keiji Hirose、Koichiro Naemura

  DOI：10.1021/jo980441p

  日期：1998.10.1

  Dithiourea 1a self-assembles to form an orthogonal dimer structure both in solution and in the solid state, wherein the four thiourea groups establish a closed network of hydrogen bonds through a head-to-tail binding mode. This novel dimer structure was elucidated on the basis of H-1 NMR spectra, vapor pressure osmometry, and X-ray crystal structure analysis. Furthermore, a series of m-xylylene type dithioureas were synthesized and their dimerization constants (K-a) in CDCl3 were determined by dilution experiments using H-1 NMR spectroscopy. The magnitude of the K-a values are dependent on the steric bulk of the side chains, the acidity of the thiourea groups, and the weak intermolecular interaction between the benzene rings of the side chains and the m-xylylene spacer.
• Design, synthesis and in vitro evaluation of novel bivalent S-adenosylmethionine analogues
  作者：Catherine Joce、Rebecca White、Peter G. Stockley、Stuart Warriner、W. Bruce Turnbull、Adam Nelson

  DOI：10.1016/j.bmcl.2011.11.017

  日期：2012.1

  In optimal cases, bivalent ligands can bind with exceptionally high affinity to their protein targets. However, designing optimised linkers, that orient the two binding groups perfectly, is challenging, and yet crucial in both fragment-based ligand design and in the discovery of bisubstrate enzyme inhibitors. To further our understanding of linker design, a series of novel bivalent S-adenosylmethionine (SAM) analogues were designed with the aim of interacting with the MetJ dimer in a bivalent sense (1:1 ligand/MetJ dimer). A range of ligands was synthesised and analyzed for ability to promote binding of the Escherichia coli methionine repressor, MetJ, to its operator DNA. Binding of bivalent SAM analogues to the MetJ homodimer in the presence of operator DNA was evaluated by fluorescence anisotropy and the effect of linker length and structure was investigated. The most effective bivalent ligand identified had a flexible linker, and promoted the DNA-protein interaction at 21-times lower concentration than the corresponding monovalent control compound. (C) 2011 Elsevier Ltd. All rights reserved.