3-(N-nonyl-N-benzoylamino)-5-bromo-N'-methylbenzanilide | 1268704-11-5

• 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: 3-(N-nonyl-N-benzoylamino)-5-bromo-N'-methylbenzanilide
• 英文别名: 3-[benzoyl(nonyl)amino]-5-bromo-N-methyl-N-phenylbenzamide
• CAS: 1268704-11-5
• 化学式: C₃₀H₃₅BrN₂O₂
• 分子量: 535.524
• InChiKey: LXJVYKDOUSKMBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(N-nonyl-N-benzoylamino)-5-bromo-N'-methylbenzanilide 、 1-芘硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  A screw-shaped alignment of pyrene using m-calix[3]amide

  摘要：

  m-Calix[3]amide bearing three pyrenes (1a) was prepared by the condensation reaction of 3-nonylaminobenzoic acid derivative using Ph3PCl2. Pyrenyl groups were found to be aligned in the screw-like fashion by m-calix[3]amide as confirmed by the X-ray crystallography. Aromatic proton signals observed at the up-field region in the H-1 NMR spectrum at low temperature indicated that pyrenyl groups in 1a are aligned in close proximity in THF solution. UV-vis absorption and fluorescence emission spectra did not show marked peak shift nor concentration fluorescence quenching compared with reference compounds implying no significant electronic interaction between pyrenyl groups. These results can be explained by the steric effect of the m-calix[3]amide platform. On the other hand, an excimer emission was observed for m-calix[3]amide having a flexible spacer between pyrene and m-calix[3] amide (1b). (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.015
• 作为产物：
  描述：

  3-氨基-5-溴苯甲酸甲酯 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.0h， 生成 3-(N-nonyl-N-benzoylamino)-5-bromo-N'-methylbenzanilide
  参考文献：
  名称：

  Self-Assembly of Oligothiophene Chromophores by m-Calix[3]amide Scaffold

  摘要：

  m-Calix[3]amides carrying the bithiophene chromophore (BTC3A) and terthiophene chromophore (TTC3A) were synthesized by the cyclic trimerization of m-aminobenzoic acid esters for the purpose of the control and understanding of the self-assembly of oligothiophene chromophores. Polymers and model compounds were also prepared for comparison. From the (1)H NMR experiments, cyclic trimer BTC3A showed the syn/ anti equilibrium in solution, and the syn/anti conformer ratio (76/24 in CDCl(3)) was influenced by the solvent character. Namely, the population of the syn conformer was lowest (70%) in THF-d(8) and was highest (86%) in CDCl(3)/CD(3)OD (1/1 in volume). On the other hand, the population of the syn conformer of cyclic trimer TTC3A was high (84%) even in CDCl(3). In a CHCl(3) solution of cyclic trimer BTC3A, the absorption maximum (342 nm) blue-shifted and the emission maximum (448 nm) red-shifted compared with those of polymer BTPA and model compound BTM. The solvent character also had an impact on the optical properties of cyclic trimer BTC3A. The red-shifted emission maximum (481 nm) of cyclic trimer BTC3A in CH(3)OH indicated the interaction between three bithiophene chromophores. The emission maxima of cyclic trimer TTC3A (486 nm) demonstrated a small red-shift from model compound TTM (477 nm), and no solvent dependency was observed, unlike cyclic trimer BTC3A.

  DOI：

  10.1021/jo102160x

文献信息

• Helicity Induction in Three π-Conjugated Chromophores by Planar Chirality of Calixamide
  作者：Ryohei Yamakado、Koichiro Mikami、Koji Takagi、Isao Azumaya、Shinri Sugimoto、Shin-ichi Matsuoka、Masato Suzuki、Kosuke Katagiri、Masanobu Uchiyama、Atsuya Muranaka

  DOI：10.1002/chem.201301198

  日期：2013.9.2

  Shall we twist? Three‐dimensional arrangement of π‐conjugated chromophores with triple‐stranded helicity was achieved by using the planar chirality of m‐calix[3]amide (see figure). Based on spectroscopic data and theoretical calculations, the dynamic and preferred helical characters of bithiophene units embedded in the tubular molecule were elucidated, and the absolute configuration was determined

  我们可以扭转吗？通过使用m- calix [3]酰胺的平面手性，实现了具有三链螺旋的π共轭生色团的三维排列。根据光谱数据和理论计算，阐明了嵌入管状分子中的联噻吩单元的动态和优选螺旋特征，并确定了其绝对构型。
• A screw-shaped alignment of pyrene using m-calix[3]amide
  作者：Ryohei Yamakado、Shin-ichi Matsuoka、Masato Suzuki、Koji Takagi、Kosuke Katagiri、Isao Azumaya

  DOI：10.1016/j.tet.2012.12.015

  日期：2013.2

  m-Calix[3]amide bearing three pyrenes (1a) was prepared by the condensation reaction of 3-nonylaminobenzoic acid derivative using Ph3PCl2. Pyrenyl groups were found to be aligned in the screw-like fashion by m-calix[3]amide as confirmed by the X-ray crystallography. Aromatic proton signals observed at the up-field region in the H-1 NMR spectrum at low temperature indicated that pyrenyl groups in 1a are aligned in close proximity in THF solution. UV-vis absorption and fluorescence emission spectra did not show marked peak shift nor concentration fluorescence quenching compared with reference compounds implying no significant electronic interaction between pyrenyl groups. These results can be explained by the steric effect of the m-calix[3]amide platform. On the other hand, an excimer emission was observed for m-calix[3]amide having a flexible spacer between pyrene and m-calix[3] amide (1b). (c) 2012 Elsevier Ltd. All rights reserved.
• Self-Assembly of Oligothiophene Chromophores by <i>m</i>-Calix[3]amide Scaffold
  作者：Koji Takagi、Shinri Sugimoto、Ryohei Yamakado、Katsuya Nobuke

  DOI：10.1021/jo102160x

  日期：2011.4.15

  m-Calix[3]amides carrying the bithiophene chromophore (BTC3A) and terthiophene chromophore (TTC3A) were synthesized by the cyclic trimerization of m-aminobenzoic acid esters for the purpose of the control and understanding of the self-assembly of oligothiophene chromophores. Polymers and model compounds were also prepared for comparison. From the (1)H NMR experiments, cyclic trimer BTC3A showed the syn/ anti equilibrium in solution, and the syn/anti conformer ratio (76/24 in CDCl(3)) was influenced by the solvent character. Namely, the population of the syn conformer was lowest (70%) in THF-d(8) and was highest (86%) in CDCl(3)/CD(3)OD (1/1 in volume). On the other hand, the population of the syn conformer of cyclic trimer TTC3A was high (84%) even in CDCl(3). In a CHCl(3) solution of cyclic trimer BTC3A, the absorption maximum (342 nm) blue-shifted and the emission maximum (448 nm) red-shifted compared with those of polymer BTPA and model compound BTM. The solvent character also had an impact on the optical properties of cyclic trimer BTC3A. The red-shifted emission maximum (481 nm) of cyclic trimer BTC3A in CH(3)OH indicated the interaction between three bithiophene chromophores. The emission maxima of cyclic trimer TTC3A (486 nm) demonstrated a small red-shift from model compound TTM (477 nm), and no solvent dependency was observed, unlike cyclic trimer BTC3A.