4-dimethylamino-β-ethyl-β-nitrostyrene | 134538-51-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-dimethylamino-β-ethyl-β-nitrostyrene
• 英文别名: 4-Dimethyamino-beta-ethyl-beta-nitrostyrene；N,N-dimethyl-4-[(E)-2-nitrobut-1-enyl]aniline
• CAS: 134538-51-5
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: SUARUWFMIRQYMS-PKNBQFBNSA-N

物化性质

• 熔点：
  90-91.5 °C(Solvent: Methanol)
• 沸点：
  355.9±25.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硝基丙烷 、 对二甲氨基苯甲醛 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 50.0 ℃ 、999.99 MPa 条件下， 反应 3.0h， 以54%的产率得到4-dimethylamino-β-ethyl-β-nitrostyrene
  参考文献：
  名称：

  Henry condensation under high pressure 2. Effect of aromatic aldehyde type and pressure on the yield of ?-nitrostyrenes and secondary processes

  摘要：

  Condensation of aromatic aldehydes (I)-(XX) with EtNO2 and n-PrNO2 in AcOH in the presence of AcONH4 or i-BuNH2 gives primarily omega-nitrostyrenes (Ia, b)-(XXa, b) and small quantities of nitriles (Ic)-(XXc), oximes (Id)-(XXd), and ketones (Ie, f)-(XXe, f). The yields of (Ia, b)-(XXa, b) at P = 1 atm are higher for acceptor substituents on the aromatic ring whereas at P = 10 kbar, they are higher for donor substituents. High pressures suppress the formation of (Ic-f)-(XXc-f) and the Z-isomers of (Ia, b)-(XXa, b). The high pressure technique is especially useful in the preparation of donor-substituted (Ia, b)-(XXa, b) which are intermediates in the synthesis of the psychotropic beta-phenylethylamines.

  DOI：

  10.1007/bf00965433

文献信息

• 4-Dimethylamino-β-nitrostyrene and 4-dimethylamino-β-ethyl-β-nitrostyrene at 100 K
  作者：Lamine Hamdellou、Olivier Hernandez、Jean Meinnel

  DOI：10.1107/s0108270106025819

  日期：2006.8.11

  The structures of 4-dimethylamino-beta-nitrostyrene (DANS), C10H12N2O2, and 4-dimethylamino-beta-ethyl-beta-nitrostyrene (DAENS), C12H16N2O2, have been solved at T = 100 K. The structure solution for DANS was complicated by the presence of a static disorder, characterized by a misorientation of 17% of the molecules. The molecule of DANS is almost planar, indicating significant conjugation, with a push-pull effect through the styrene skeleton extending up to the terminal substituents and enhancing the dipole moment. As a consequence of this conjugation, the hexagonal ring displays a quinoidal character; the lengths of the C-N [1.3595 (15) angstrom] and C-C [1.448 (2) angstrom] bonds adjacent to the benzene ring are shorter than single bonds. The molecules are stacked in dimers with antiparallel dipoles. In contrast, the molecule of DAENS is not planar. The ethyl substituent pushes the nitropropene group out of the benzene plane, with a torsion angle of -21.9 (3). Nevertheless, the molecule remains conjugated, with a shortening of the same bonds as in DANS.
• Henry condensation under high pressure 2. Effect of aromatic aldehyde type and pressure on the yield of ?-nitrostyrenes and secondary processes
  作者：N. E. Agafonov、I. P. Sedishev、A. V. Dudin、A. A. Kutin、G. A. Stashina、V. M. Zhulin

  DOI：10.1007/bf00965433

  日期：1991.2

  Condensation of aromatic aldehydes (I)-(XX) with EtNO2 and n-PrNO2 in AcOH in the presence of AcONH4 or i-BuNH2 gives primarily omega-nitrostyrenes (Ia, b)-(XXa, b) and small quantities of nitriles (Ic)-(XXc), oximes (Id)-(XXd), and ketones (Ie, f)-(XXe, f). The yields of (Ia, b)-(XXa, b) at P = 1 atm are higher for acceptor substituents on the aromatic ring whereas at P = 10 kbar, they are higher for donor substituents. High pressures suppress the formation of (Ic-f)-(XXc-f) and the Z-isomers of (Ia, b)-(XXa, b). The high pressure technique is especially useful in the preparation of donor-substituted (Ia, b)-(XXa, b) which are intermediates in the synthesis of the psychotropic beta-phenylethylamines.