(Z)-4-benzylidene-2-(4-bromophenyl)oxazol-5(4H)-one | 849770-61-2

• 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: (Z)-4-benzylidene-2-(4-bromophenyl)oxazol-5(4H)-one
• 英文别名: (4Z)-2-(4-Bromophenyl)-4-(phenylmethylidene)-4,5-dihydro-1,3-oxazol-5-one；(4Z)-4-benzylidene-2-(4-bromophenyl)-1,3-oxazol-5-one
• CAS: 849770-61-2
• 化学式: C₁₆H₁₀BrNO₂
• 分子量: 328.165
• InChiKey: HUBZEPXXAJTDMV-UVTDQMKNSA-N

物化性质

• 熔点：
  187-189 °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：

  (Z)-4-benzylidene-2-(4-bromophenyl)oxazol-5(4H)-one 在 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以56%的产率得到(5Z)-5-benzylidene-2-(4-bromophenyl)-3,5-dihydro-4H-imidazol-4-one
  参考文献：
  名称：

  [（4 Z）-2-芳基-4-（芳基亚甲基）-5-氧代-4,5-二氢-1 H-咪唑-1-基]链烷酸的合成及抗胆碱酯酶活性

  摘要：

  通过N-取代的α，β-脱氢肽反应合成ω-[（4 Z）-2-芳基-4-芳基亚甲基-5-氧代-4,5-二氢-1 H-咪唑-1-基]链烷酸与氯（三甲基）硅烷或1,1,1,3,3,3-六甲基二硅氮烷。测试初始肽和基于其的（4 H）-咪唑-5-酮衍生物的抗胆碱酯酶活性。

  DOI：

  10.1134/s1070428018090178
• 作为产物：
  描述：

  N-(4-溴苯甲酰基)-甘氨酸 、 苯甲醛 在 sodium acetate 、 乙酸酐 作用下， 生成 (Z)-4-benzylidene-2-(4-bromophenyl)oxazol-5(4H)-one
  参考文献：
  名称：

  Phenylpropenamide derivatives as inhibitors of Hepatitis B virus replication

  摘要：

  A non-nucleoside class of compounds that inhibits the replication of hepatitis B virus (HBV) in cell culture has been discovered. A series of substituted analogues of phenylpropenamide 6 has been prepared and evaluated in the HepAD38 cellular assay. Structure-activity relationships of this series are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00544-8

文献信息

• 3-Isothiocyanato Oxindoles Serving as Powerful and Versatile Precursors to Structurally Diverse Dispirocyclic Thiopyrrolidineoxindoles through a Cascade Michael/Cyclization Process with Amino-Thiocarbamate Catalysts
  作者：Wen-Yong Han、Shi-Wu Li、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1002/chem.201300206

  日期：2013.4.26

  Cascading catalysis: 3‐Isothiocyanato oxindoles act as powerful and versatile precursors for a range of structurally diverse dispirocyclic thiopyrrolidineoxindoles containing two spiro‐quaternary and three contiguous stereogenic centers in quantitative yields with excellent disatereo‐ and enantioselectivities by only using 1 mol % amino‐thiocarbamate catalyst.

  级联催化：3-异硫氰酸根合吲哚是一系列结构多样的二螺环硫代吡咯烷并吲哚的有力且用途广泛的前体，仅使用1 mol％氨基硫代氨基甲酸酯催化剂，其定量收率就具有两个螺-季四和三个连续的立体中心，并具有优异的对映和对映选择性。 。
• Synthesis and anticholinesterase activity of 2-(dimethylamino)ethyl and choline esters of n-substituted α, β-dehydroamino acids
  作者：A. A. Grigoryan、A. A. Ambartsumyan、M. V. Mkrtchyan、V. O. Topuzyan、G. P. Alebyan、R. S. Asatryan

  DOI：10.1007/s11094-006-0077-8

  日期：2006.3

  A new method for the synthesis of tertiary and quaternary aminoesters of N-substituted α,β-dehydroamino acids is described. Aseries of 16 dehydroamino acids esterified to choline or to its tertiary analog have been synthesized by the proposed method with a yield of 84–93%, and their interactions with human erythrocyte acetylcholinesterase (ACE) and human plasma butyrylcholinesterase (BCE) has been studied. The half-inhibiting concentrations IC50 of the synthesized compounds (determined with respect to cholinesterase hydrolysis of a model substrate, 0.1 mM ATC) vary within a broad range (0.16–1840 µM). The values of traditional parameters of the wave functions of ligands estimated using the Hartree-Fock method do not explain the observed pattern of the anticholinesterase activity. The specific properties of the molecules, especially in their quaternary ammonium salt forms, are probably related to their structural features, in particular, to the ability of the inhibitors to form cyclic conformations (so-called crown structures). Such structures are probably stabilized as a result of the formation of intramolecuar hydrogen bonds between protons of the choline residue and oxygen of the terminal peptide group.

  本文介绍了一种合成 N-取代的 α、β-脱氢氨基酸的三级和四级氨基酯的新方法。通过所提出的方法合成了 16 种与胆碱或其三级类似物酯化的脱氢氨基酸系列，产率为 84-93%，并研究了它们与人红细胞乙酰胆碱酯酶（ACE）和人血浆丁酰胆碱酯酶（BCE）的相互作用。合成化合物的半抑制浓度 IC50（根据胆碱酯酶水解模型底物 0.1 mM ATC 测定）在很宽的范围内变化（0.16-1840 µM）。使用哈特里-福克方法估算的配体波函数的传统参数值并不能解释所观察到的抗胆碱酯酶活性模式。分子的特殊性质，尤其是季铵盐形式的分子，可能与它们的结构特征有关，特别是与抑制剂形成环状构象（所谓的冠状结构）的能力有关。这种结构的稳定可能是胆碱残基的质子与末端肽基的氧之间形成分子内氢键的结果。
• Tandem Michael Addition–Ring Transformation Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with Olefinic Azlactones: Direct Access to Structurally Diverse Spirocyclic Oxindoles
  作者：Bao-Dong Cui、Jian Zuo、Jian-Qiang Zhao、Ming-Qiang Zhou、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1021/jo500432c

  日期：2014.6.6

  An efficient method for the direct construction of two classes of spirocyclic oxindoles by the reactions of 3-hydroxyoxindoles/3-aminooxindoles and (Z)-olefinic azlactones through a tandem Michael addition-ring transformation process has been developed. With DBU as the catalyst, a range of spiro-butyrolactoneoxindoles and spiro-butyrolactamoxindoles, containing an oxygen or a nitrogen heteroatom, respectively, in the spiro stereocenter, were smoothly obtained with good to excellent diastereoselectivities in high yields.
• EL-SHARIEF, A. M. SH.;HARB, A. A., INDIAN J. CHEM., 1982, 21, N 5, 449-453
  作者：EL-SHARIEF, A. M. SH.、HARB, A. A.

  DOI：——

  日期：——
• ISLAM, A. M.;EL-SHARIEF, A. M. SH.;ISMAIL, I. M.;HARB, A. A., EGYPT. J. CHEM., 1983, 26, N 3, 221-232
  作者：ISLAM, A. M.、EL-SHARIEF, A. M. SH.、ISMAIL, I. M.、HARB, A. A.

  DOI：——

  日期：——