4-(p-Chloranilino)-3-penten-2-on | 51218-07-6

• 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: 4-(p-Chloranilino)-3-penten-2-on
• 英文别名: 4-(4-Chloro-phenylamino)pent-3-en-2-one；(E)-4-(4-chloroanilino)pent-3-en-2-one
• CAS: 51218-07-6；56570-36-6
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: SXTAJDWMNCVVPD-BQYQJAHWSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  326.1±42.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  劳森试剂 、 4-(p-Chloranilino)-3-penten-2-on 以20%的产率得到
  参考文献：
  名称：

  WALTER W.; PROLL T., SYNTHESIS, 1979, NO 12, 941-942

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯胺 、 乙酰丙酮 在 ammonium cerium(IV) nitrate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以76%的产率得到4-(p-Chloranilino)-3-penten-2-on
  参考文献：
  名称：

  General, Mild and Efficient Synthesis of β-Enaminones Catalyzed by Ceric Ammonium Nitrate

  摘要：

  铈铵硝酸盐催化芳香族或脂肪族初级胺与多种β-二羰基化合物的反应，包括β-酮酯、β-酮硫酯和β-二酮。该反应在室温下顺利进行，反应时间短，产物为β-烯酰胺，产率良好至优异。

  DOI：

  10.1055/s-2007-973862

文献信息

• Synthesis and anticonvulsant activity of enaminones. 2. Further structure-activity correlations
  作者：K. R. Scott、Ivan O. Edafiogho、Erica L. Richardson、Vida A. Farrar、Jacqueline A. Moore、Elizabeth I. Tietz、Christine N. Hinko、Hyejung Chang、Afif El-Assadi、Jesse M. Nicholson

  DOI：10.1021/jm00066a003

  日期：1993.7

  shown to be safer alternatives, the most notable was methyl 4-[(p-bromophenyl)amino]-6-methyl-2-oxocyclohex-3-en-1-oate, 13. Compound 13 had an ip ED50 of 4 mg/kg in the rat and a TD50 of 269 mg/kg, providing a protective index (TD50/ED50) of > 67. By variation in the ring size, additional aromatic substitutions and the synthesis of acyclic analogs, these newer compounds provide a more definitive insight

  该报告继续对4-[（对氯苯基）氨基] -6-甲基-2-氧代环己基-3-烯-1-酸酯1（ADD 196022）和甲基4-（苄基氨基）进行深入评估-6-甲基-2-氧代环己基-3-烯-1-酸酯，2个，两个有效的抗惊厥性烯胺酮。这些化合物采用杏仁核点燃模型进行评估。1和2都没有针对杏仁核点燃的癫痫发作的活性，进一步支持了角膜点燃的模型作为抗电击癫痫发作评估的确定工具，如先前报道。关于1的其他腹膜内（ip）数据显示，在100 mg / kg的24小时内有毒性。为了使毒性最小化，已经制备了几种活性类似物。在由抗癫痫药物开发（ADD）计划开发的特殊ip大鼠屏幕中，对这些新的类似物进行了评估，以防最大剂量10 mg / kg的电击惊厥（MES）和100 mg / kg的神经毒性。从该筛选中，显示出几种化合物是更安全的替代品，最引人注目的是4-[（（对-溴苯基）氨基] -6-甲基-2-氧代环己基-3-en-
• 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.
• KOZLOV, N. S.;PAK, V. D.;BURYLOVA, L. V.;GARTMAN, G. A., DOKL. AN BSSR, 33,(1989) N2, S. 1097-1100
  作者：KOZLOV, N. S.、PAK, V. D.、BURYLOVA, L. V.、GARTMAN, G. A.

  DOI：——

  日期：——
• General, Mild and Efficient Synthesis of β-Enaminones Catalyzed by Ceric Ammonium Nitrate
  作者：J. Menéndez、Vellaisamy Sridharan、Carmen Avendaño

  DOI：10.1055/s-2007-973862

  日期：2007.4

  Ceric ammonium nitrate catalyzes the reaction between aromatic or aliphatic primary amines and a variety of β-dicarbonyl compounds, including β-ketoesters, β-ketothioesters and β-diketones. The reaction proceeds smoothly at room temperature in short reaction times and gives β-enaminones in good to excellent yields.

  铈铵硝酸盐催化芳香族或脂肪族初级胺与多种β-二羰基化合物的反应，包括β-酮酯、β-酮硫酯和β-二酮。该反应在室温下顺利进行，反应时间短，产物为β-烯酰胺，产率良好至优异。
• WALTER W.; PROLL T., SYNTHESIS, 1979, NO 12, 941-942
  作者：WALTER W.、 PROLL T.

  DOI：——

  日期：——