4-methyl-2-oxo-6-phenyl-cyclohex-3-enecarboxylic acid ethyl ester | 77548-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-2-oxo-6-phenyl-cyclohex-3-enecarboxylic acid ethyl ester
• 英文别名: 4-ethoxycarbonyl-1-methyl-3-oxo-5-phenylcyclohexene；3-methyl-6-carbethoxy-5-phenylcyclohex-2-enone；4-Methyl-2-oxo-6-phenyl-cyclohex-3-encarbonsaeure-aethylester；Ethyl 5-methyl-3-oxo-1,2,3,6-tetrahydro[1,1'-biphenyl]-2-carboxylate；ethyl 4-methyl-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate
• CAS: 77548-30-2
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: PHSJXXBXPDTQJW-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  374.6±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-2-oxo-6-phenyl-cyclohex-3-enecarboxylic acid ethyl ester 、 苯肼 以 乙醇 为溶剂， 反应 6.0h， 以70%的产率得到6-methyl-1,4-diphenyl-1,2,4,5-tetrahydro-indazol-3-one
  参考文献：
  名称：

  Analgesic, anticonvulsant and anti-inflammatory activities of some synthesized benzodiazipine, triazolopyrimidine and bis-imide derivatives

  摘要：

  A series of diazipine, pyrimidine, fused triazolopyrimidine and imide derivatives were newly synthesized using 4-phenyl-but-3-en-2-one 1 as a starting material and compounds 2 and 9 are intermediates. Initially the acute toxicity of the compounds was assayed via the determination of their LD50. All the compounds were interestingly less toxic than the reference drug. The pharmacological screening showed that many of these obtained compounds have good analgesic, anticonvulsant and anti-inflammatory activities comparable to Valdecoxib (R), Carbamazepine (R) and Predensilone (R) reference drugs. Regarding the protection against Carrageenan (R) induced edema, five compounds were found more potent than Prednisolone (R). On the other hand, in searching for COX-2 inhibitor, the inhibition of plasma PGE2 for the compounds were determined and four compounds were found more potent than Prednisolone (R). The detailed synthesis, spectroscopic data, pharmacological screening and acute toxicity LD50 for the synthesized compounds were reported. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.07.013
• 作为产物：
  描述：

  diethyl 2,6-dimethyl-1,4-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 4-methyl-2-oxo-6-phenyl-cyclohex-3-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Acid recyclization of 1,4-dihydropyridines

  摘要：

  DOI：

  10.1007/bf00475377

文献信息

• An Improved Procedure for the Michael Reaction of Chalcones
  作者：A. García-Raso、J. García-Raso、B. Campaner、R. Mestres、J. V. Sinisterra

  DOI：10.1055/s-1982-30055

  日期：——
• Vorlaender, Chemische Berichte, 1894, vol. 27, p. 2058
  作者：Vorlaender

  DOI：——

  日期：——
• XACHATRYAN D. S.; MORLYAN N. M.; MIRZOYAN R. G.; BADANYAN SH. O., AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM ZH., 1980, 33, HO 10, 850-855
  作者：XACHATRYAN D. S.、 MORLYAN N. M.、 MIRZOYAN R. G.、 BADANYAN SH. O.

  DOI：——

  日期：——
• XACHATRYAN, D. S.;MORLYAN, N. M.;MXITARYAN, P. V.;MIRZOYAN, R. G.;BADANYA+, ARM. XIM. ZH., 1981, 34, N 6, 480-489
  作者：XACHATRYAN, D. S.、MORLYAN, N. M.、MXITARYAN, P. V.、MIRZOYAN, R. G.、BADANYA+

  DOI：——

  日期：——
• GARCIA-RASO, A.;GARCIA-RASO, J.;CAMPANER, B.;MESTRES, R.;SINISTERRA, J. V+, SYNTHESIS, BRD, 1982, N 12, 1037-1041
  作者：GARCIA-RASO, A.、GARCIA-RASO, J.、CAMPANER, B.、MESTRES, R.、SINISTERRA, J. V+

  DOI：——

  日期：——