(E)-4-(4-Dimethylamino-phenylamino)-pent-3-en-2-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-4-(4-Dimethylamino-phenylamino)-pent-3-en-2-one
• 英文别名: (E)-4-[4-(dimethylamino)anilino]pent-3-en-2-one
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: XHOBRAGAQDUEJP-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(4-Dimethylamino-phenylamino)-pent-3-en-2-one 、 硫代异氰酸苯酯 以95%的产率得到
  参考文献：
  名称：

  WALTER W.; FLECK T., J. LIEBIGS ANN. CHEM. , 1976, NO 4, 670-681

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰丙酮 、 N,N-二甲基-对苯二胺 以86%的产率得到
  参考文献：
  名称：

  WALTER W.; FLECK T., J. LIEBIGS ANN. CHEM. , 1976, NO 4, 670-681

  摘要：

  DOI：

文献信息

• Deuterium Isotope Effects on 13C Chemical Shifts of Enaminones.
  作者：Donka Kh. Zheglova、Daniel G. Genov、Simon Bolvig、Poul Erik Hansen、M. Hanfland、E. Dooryhee

  DOI：10.3891/acta.chem.scand.51-1016

  日期：——

  Deuterium isotope effects on C-13 chemical shifts have been studied in a series of substituted N-alkyl and N-phenyl keto-enamines. The intramolecularly hydrogen bonded Z-forms show the largest two-bond isotope effects, (2) Delta C-1(ND). Methyl-substitution al C-l leads to a larger two-bond isotope effect in the N-phenyl-substituted derivatives. This effect is ascribed to steric compression. Space-filling substituents at the ortho-position of the N-phenyl ring lead to a decrease of the two-bond isotope effect. A correlation is found between (2) Delta C-1(ND) and (3) Delta C-2'(ND). The latter becomes negative in the sterically hindered cases. (3) Delta C-2'(ND) may therefore be used as a gauge of the twist of the phenyl ring.o-Hydroxy substitution of the CO-phenyl rings enables intramolecular hydrogen bonding to the carbonyl group. This kind of hydrogen bond with two donors to one acceptor leads to smaller (2) Delta C-2(ND) and (2) Delta C-2 ''(OD) isotope effects equivalent to weaker hydrogen bonds for the Z-isomer. This is ascribed to competition for the acceptor. For the E-isomer (2) Delta C(OD) is enhanced. The same feature is seen for N,N-dimethylamino enamines. This increase is ascribed to delocalization of the nitrogen lone-pair onto the carbonyl oxygen, thereby strengthening the hydrogen bond and thus leading to larger two-bond, (2) Delta C(OD), isotope effects.
• WALTER W.; FLECK T., J. LIEBIGS ANN. CHEM. <JLAC-BF>, 1976, NO 4, 670-681
  作者：WALTER W.、 FLECK T.

  DOI：——

  日期：——