4-[1-(4-Methoxy-phenyl)-eth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one | 69015-82-3

• 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: 4-[1-(4-Methoxy-phenyl)-eth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one
• 英文别名: 4-[1-(4-Methoxyphenyl)ethylidene]-2-phenyl-1,3-oxazol-5(4H)-one；4-[1-(4-methoxyphenyl)ethylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 69015-82-3
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: KWJOUDYKPRVRCO-UHFFFAOYSA-N

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：

  甲醇 、 4-[1-(4-Methoxy-phenyl)-eth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one 在 sodium methylate 作用下， 反应 2.0h， 生成 Z-2-benzoylamino-3-p-methoxyphenyl-2-butenoic acid
  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

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。
• Organocatalytic Asymmetric Hetero-Diels–Alder Reaction of in Situ Generated Dienes: Access to α,β-Unsaturated δ-Lactones Featuring CF₃-Substituted Quaternary Stereocenter
  作者：Harshit Joshi、Ankit Yadav、Arko Das、Vinod K. Singh

  DOI：10.1021/acs.joc.9b03076

  日期：2020.3.6

  Chiral bifunctional urea-catalyzed asymmetric direct hetero-Diels-Alder reaction between alkylidene azlactone-derived dienes and trifluoromethyl aryl ketones is reported for the first time. The direct hetero-Diels-Alder reaction followed by ring opening results in densely functionalized α,β-unsaturated δ-lactones featuring a CF3-substituted quaternary stereocenter in high yields with excellent enantioselectivities

  首次报道了亚烷基a内酯衍生的二烯与三氟甲基芳基酮之间的手性双官能尿素催化的不对称直接杂Diels-Alder反应。直接的异狄尔斯-阿尔德反应和随后的开环导致以CF 3取代的季立体中心为特征的致密官能化的α，β-不饱和δ-内酯，具有高收率和优异的对映选择性。该方法在一定范围的基材上兼容。此外，扩大反应规模，并将α，β-不饱和δ-内酯转化为装饰有三氟甲基化甲醇官能度的氨基酸衍生物。
• Phase-Transfer-Catalyzed, Enantioselective Vinylogous Conjugate Addition–Cyclization of Olefinic Azlactones To Access Multifunctionalized Chiral Cyclohexenones
  作者：Bo Zhu、Bohua Lu、Huifang Zhang、Xinyao Xu、Zhiyong Jiang、Junbiao Chang

  DOI：10.1021/acs.orglett.9b01001

  日期：2019.5.3

  An asymmetric, phase-transfer-catalyzed vinylogous conjugate addition–vinylogous cyclization cascade of olefinic azlactones with 4-nitro-5-styrylisoxazoles is reported. In the presence of an l-tert-leucine-derived urea–quaternary ammonium salt as a bifunctional phase-transfer catalyst and KF, two series of valuable optically pure cyclohexenones featuring two and three stereocenters were obtained in

  报道了烯丙基内酯与4-硝基-5-苯乙烯基恶唑的不对称相转移催化乙烯基共轭加成-乙烯基环化级联反应。在一个存在升-叔-亮氨酸衍生的脲-季铵盐作为双官能相转移催化剂和KF，以高收率和良好至优异的对映得到两个系列的有价值的光学纯环己烯酮具有两个和三个立体和非对映选择性。
• Side Chain Methyl Substitution in the δ-Opioid Receptor Antagonist TIPP Has an Important Effect on the Activity Profile
  作者：Dirk Tourwé、Els Mannekens、Trang Nguyen Thi Diem、Patricia Verheyden、Hendrika Jaspers、Géza Tóth、Antal Péter、István Kertész、Gabriella Török、Nga N. Chung、Peter W. Schiller

  DOI：10.1021/jm981011u

  日期：1998.12.1

  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.