2-phenyl-4-<α-E-p-methoxyphenylethylidene>-5(4H)-oxazolone | 57427-93-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-phenyl-4-<α-E-p-methoxyphenylethylidene>-5(4H)-oxazolone
• 英文别名: E-2-phenyl-4-(α-p-methoxyphenylethylidene)-5(4H)-oxazolone；4-[1-(4-methoxy-phenyl)-ethylidene]-2-phenyl-4H-oxazol-5-one；(4E)-4-[1-(4-methoxyphenyl)ethylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 57427-93-7
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: KWJOUDYKPRVRCO-FOWTUZBSSA-N

物化性质

• 熔点：
  169 °C
• 沸点：
  441.0±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-<α-E-p-methoxyphenylethylidene>-5(4H)-oxazolone 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、344.74 kPa 条件下， 反应 6.0h， 生成 erythro-N-benzoyl-β-methyl-p-methoxy-phenylalanine methyl ester
  参考文献：
  名称：

  Side Chain Methyl Substitution in the δ-Opioid Receptor Antagonist TIPP Has an Important Effect on the Activity Profile

  摘要：

  The delta-opioid antagonist H-Tyr-Tic-Phe-Phe-OH (TIPP-OH) or its C-terminal amide analogue was systematically modified topologically by substitution of each amino acid residue by all stereoisomers of the corresponding beta-methyl amino acid. The potency and selectivity (delta- vs mu- and kappa-opioid receptor) were evaluated by radioreceptor binding assays. Agonist or antagonist potency were assayed in the mouse vas deferens and in the guinea pig ileum. In the TIPP analogues containing L-beta-methyl amino acids the influence on delta-receptor affinity and on delta-antagonist potency is limited, the [(2S,3R)-beta-MePhe(3)]TIPP-OH analogue being among the most potent delta-antagonists reported. In the D-beta-methyl amino acid series, the [D-beta-MeTic(2)] analogues are delta-selective antagonists whereas [D-Tic(2)]TIPP-NH2 is a delta-agonist. NMR studies did not indicate any influence of the beta-methyl substituent on the conformation of the Tic residue. The [(2R,3S)-beta-MePhe(3)]TIPP-NH2 is a potent delta-agonist, its C-terminal carboxylic acid analogue being more delta-selective but displaying partial agonism in both the delta- and mu-bioassay. These results constitute further examples of a profound influence of beta-methyl substitution on the potency, selectivity, and signal transduction properties of a peptide.

  DOI：

  10.1021/jm981011u
• 作为产物：
  描述：

  2-phenyl-4-<α-Z-p-methoxyphenylethylidene>-5(4H)-oxazolone 在 氢溴酸 作用下， 以 苯 为溶剂， 以90%的产率得到2-phenyl-4-<α-E-p-methoxyphenylethylidene>-5(4H)-oxazolone
  参考文献：
  名称：

  Cativiela, C.; Diaz de Villegas, M. D.; Melendez, E., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1655 - 1657

  摘要：

  DOI：

文献信息

• A catalytic asymmetric hetero-Diels–Alder reaction of olefinic azlactones and isatins: facile access to chiral spirooxindole dihydropyranones
  作者：Tai-Ping Gao、Jun-Bing Lin、Xiu-Qin Hu、Peng-Fei Xu

  DOI：10.1039/c4cc03896g

  日期：——

  A catalytic asymmetric hetero-Diels-Alder (HDA) reaction has been achieved through hydrogen-bond directed gamma-addition of olefinic azlactones to isatins. This methodology provides an efficient access to spirooxindole dihydropyranones in moderate to good yields and with excellent enantioselectivities.

  催化不对称杂Diels-Alder（HDA）反应是通过氢键直接将烯烃a内酯加到isatins上的伽马加成反应而实现的。这种方法可以高效，高效地获得螺环吲哚二氢吡喃酮，并且具有出色的对映选择性。
• On the synthesis of methyl (z/e)-2-acetamido(or benzamido)-3-aryl 2-butenoates
  作者：C. Cativiela、M.D. Diaz de Villegas、E. Nelendez

  DOI：10.1016/s0040-4020(01)87457-3

  日期：1986.1
• CATIVIELA, C.;DIAZ, DE, VILLEGAS, M. D.;MELENDEZ, E., TETRAHEDRON, 1986, 42, N 2, 583-589
  作者：CATIVIELA, C.、DIAZ, DE, VILLEGAS, M. D.、MELENDEZ, E.

  DOI：——

  日期：——
• CATIVIELA, C.;DIAZ, DE, VILLEGAS, M. D.;MELENDEZ, E., J. HETEROCYCL. CHEM., 1985, 22, N 6, 1655-1657
  作者：CATIVIELA, C.、DIAZ, DE, VILLEGAS, M. D.、MELENDEZ, E.

  DOI：——

  日期：——