<2-(N,N-dimethyl-p-phenylenediamino)-vinyl> phenyl ketone | 160534-31-6

• 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: <2-(N,N-dimethyl-p-phenylenediamino)-vinyl> phenyl ketone
• 英文别名: (Z)-3-[4-(dimethylamino)anilino]-1-phenylprop-2-en-1-one
• CAS: 160534-31-6
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: NZADGJKUXBUGCH-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  <2-(N,N-dimethyl-p-phenylenediamino)-vinyl> phenyl ketone 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N-(p-N,N-dimethylanilino)-S-methyl N-(3-oxo-3-phenyl-propen-1-yl)-N'-phenyl isothiourea
  参考文献：
  名称：

  REACTION OF ENAMINONES WITH THIACUMULENES

  摘要：

  Enaminones 2, easily prepared from the corresponding sodium salts of beta -ketoaldehydes 1 and hydrochlorides of primary amines, react with carbon disulfide/sodium hydride to give dithiocarbamates 3 after alkylation. In a similar way thiocarbamoylation yields isothioureas 4. The C-13 NMR parameters of 2, 3 and 4 show significant low- and high-field shifts of the C-1 and C-2 signals, respectively.

  DOI：

  10.1080/10426509808032471
• 作为产物：
  描述：

  4-dimethylaminophenylamine dihydrochloride 、 benzoylacetaldehyde sodium salt 以 水 为溶剂， 反应 0.5h， 以99%的产率得到<2-(N,N-dimethyl-p-phenylenediamino)-vinyl> phenyl ketone
  参考文献：
  名称：

  REACTION OF ENAMINONES WITH THIACUMULENES

  摘要：

  Enaminones 2, easily prepared from the corresponding sodium salts of beta -ketoaldehydes 1 and hydrochlorides of primary amines, react with carbon disulfide/sodium hydride to give dithiocarbamates 3 after alkylation. In a similar way thiocarbamoylation yields isothioureas 4. The C-13 NMR parameters of 2, 3 and 4 show significant low- and high-field shifts of the C-1 and C-2 signals, respectively.

  DOI：

  10.1080/10426509808032471

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.
• REACTION OF ENAMINONES WITH THIACUMULENES
  作者：Swapan Kumar Chatterjee、Wolf-Dieter Rudorf

  DOI：10.1080/10426509808032471

  日期：1998.1

  Enaminones 2, easily prepared from the corresponding sodium salts of beta -ketoaldehydes 1 and hydrochlorides of primary amines, react with carbon disulfide/sodium hydride to give dithiocarbamates 3 after alkylation. In a similar way thiocarbamoylation yields isothioureas 4. The C-13 NMR parameters of 2, 3 and 4 show significant low- and high-field shifts of the C-1 and C-2 signals, respectively.