2-(4-Bromo-phenyl)-4-[1-phenyl-meth-(Z)-ylidene]-4H-oxazol-5-one | 84156-19-4

• 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-(4-Bromo-phenyl)-4-[1-phenyl-meth-(Z)-ylidene]-4H-oxazol-5-one
• 英文别名: 4-Benzylidene-2-(4-bromophenyl)-1,3-oxazol-5-one
• CAS: 84156-19-4
• 化学式: C₁₆H₁₀BrNO₂
• mdl: MFCD00428579
• 分子量: 328.165
• InChiKey: HUBZEPXXAJTDMV-UHFFFAOYSA-N

物化性质

• 熔点：
  186 °C(Solv: ethanol (64-17-5))
• 沸点：
  424.9±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Bromo-phenyl)-4-[1-phenyl-meth-(Z)-ylidene]-4H-oxazol-5-one 在 sodium acetate 、 zinc(II) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 9.0h， 生成 2-(4-Bromo-phenyl)-3-(9-methyl-acridin-2-yl)-5-[1-phenyl-meth-(Z)-ylidene]-3,5-dihydro-imidazol-4-one
  参考文献：
  名称：

  Sharief, A. M. Sh. El-; Harb, A.A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 5, p. 449 - 453

  摘要：

  DOI：
• 作为产物：
  描述：

  dehydrophenylalanine 、 对溴苯甲醛 在 sodium acetate 、 乙酸酐 作用下， 以85%的产率得到2-(4-Bromo-phenyl)-4-[1-phenyl-meth-(Z)-ylidene]-4H-oxazol-5-one
  参考文献：
  名称：

  Sharief, A. M. Sh. El-; Harb, A.A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 5, p. 449 - 453

  摘要：

  DOI：

文献信息

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  DOI：10.1016/j.bmc.2020.115892

  日期：2021.1

  As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value

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  DOI：10.1002/anie.201916534

  日期：2020.3.23

  chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2-amidoacrylates, affording the chiral α-amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000).

  发现富含地球的镍与合适的手性双膦配体配合使用，是2-酰胺基丙烯酸酯不对称氢化的有效催化剂，以定量收率和优异的对映选择性（高达96％ee）提供了手性α-氨基酸酯。通过NMR和HRMS对活性催化剂组分进行了研究，这有助于我们以克级实现高催化效率且催化剂负载量低（S / C = 2000）。氢化产物可以简单地转化为手性α-氨基酸，β-氨基醇及其生物活性衍生物。此外，使用氘标记实验和计算计算研究了催化机理。
• Enantioselective Synthesis of CF₃ -Containing 3,2’-Pyrrolidinyl Spirooxindoles and Dispirooxindoles via Thiourea-Catalyzed Domino Michael/Mannich [3+2] Cycloaddition Reactions
  作者：Ye Lin、Yong-Xing Song、Da-Ming Du

  DOI：10.1002/adsc.201801608

  日期：2019.3.5

  An efficient and practical organocatalytic asymmetric domino Michael/Mannich [3+2] cycloaddition of N‐2,2,2‐trifluoroethylisatin ketimines and arylidene azlactones by using a hydroquinine‐derived thiourea as the catalyst has been disclosed. Under mild conditions, a broad range of CF3‐containing 3,2’‐pyrrolidinyl spirooxindole/ dispirooxindole derivatives bearing four adjacent stereogenic centers including

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• Diastereo- and Enantioselective Construction of the Hexahydrocoumarin Scaffold via an Organocatalytic Asymmetric [3 + 3] Cyclization
  作者：Xue Yang、Yu-Chen Zhang、Qiu-Ning Zhu、Man-Su Tu、Feng Shi

  DOI：10.1021/acs.joc.6b00603

  日期：2016.6.17

  The first catalytic asymmetric construction of the biologically important hexahydrocoumarin scaffold has been established, which takes advantage of chiral thiourea–tertiary amine-catalyzed enantioselective transformations. Besides, this reaction also realized the first catalytic asymmetric [3 + 3] cyclization of 4-arylidene-2-aryloxazol-5(4H)-ones with cyclohexane-1,3-diones, which afforded structurally

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• Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs
  作者：Peiyuan Wang、Devan Naduthambi、Ralph T. Mosley、Congrong Niu、Phillip A. Furman、Michael J. Otto、Michael J. Sofia

  DOI：10.1016/j.bmcl.2011.05.077

  日期：2011.8

  Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t) ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 mu M in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.