Ethyl-3,3-dichlor-2-benzamidoacrylat | 54902-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl-3,3-dichlor-2-benzamidoacrylat
• 英文别名: α-Benzamido-β, β-dichloracrylsaeureethylester；2-benzoylamino-3,3-dichloro-acrylic acid ethyl ester；Ethyl 3,3-dichloro-2-[(phenylcarbonyl)amino]prop-2-enoate；ethyl 2-benzamido-3,3-dichloroprop-2-enoate
• CAS: 54902-32-8
• 化学式: C₁₂H₁₁Cl₂NO₃
• 分子量: 288.13
• InChiKey: KIDQRYXFVIZCHH-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±45.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl-3,3-dichlor-2-benzamidoacrylat 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以73%的产率得到ethyl 5-hydrazino-2-phenyl-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Transformations of Acylation Products of Functionally 4-Substituted 2-Alkyl(aryl)-5-hydrazino-1,3-oxazoles into 1,3,4-Oxadiazole Derivatives

  摘要：

  2-芳基-5-肼基-4-X-1,3-噁唑的酰化产物 [X = C(O)OAlk, P(O)(OAlk)2] 在加热于醋酸或乙醇时，发生重环化，转化为 1,3,4-噁二唑-2-基甘氨酸或其磷酸酯类似物的衍生物。在与吡啶中的羧酸氯化物反应时，2-烷基（芳基）-5-肼基-1,3-噁唑-4-腈也发生类似的重排，但伴随有额外的环化，涉及酰胺残基和腈基，生成 2-(5-氨基-1,3-噁唑-4-基)-1,3,4-噁二唑衍生物。

  DOI：

  10.1007/s11176-005-0244-8
• 作为产物：
  描述：

  4-(dichloromethylene)-2-phenyl-1,3-oxazol-5(4H)-one 、 乙醇 、 sodium ethanolate 以81%的产率得到
  参考文献：
  名称：

  DRACH B. S.; MISKEVICH G. N.; MARTYNYUK A. P., ZH. ORGAN. XIMII, 1978, 14, HO 3, 508-513

  摘要：

  DOI：

文献信息

• Synthesis and in vitro anticytomegalovirus activity of 5-hydroxyalkylamino-1,3-oxazoles derivatives
  作者：Esma R. Abdurakhmanova、Mykhailo Y. Brusnakov、Oleksandr V. Golovchenko、Stepan G. Pilyo、Nataliya V. Velychko、Emma A. Harden、Mark N. Prichard、Scott H. James、Victor V. Zhirnov、Volodymyr S. Brovarets

  DOI：10.1007/s00044-020-02593-6

  日期：2020.9

  A series of derivatives of 5-hydroxyalkylamino-1,3-oxazoles were synthesized. Among these derivatives, 5 compounds have been evaluated for their activities against a normal laboratory human cytomegalovirus (HCMV) strain, AD169, in human foreskin fibroblast (HFF) cells. Bioassays showed that among these, 2 compounds containing a remainder of glucamine exhibited moderate antiviral activity (compounds

  合成了一系列5-羟烷基氨基-1,3-恶唑的衍生物。在这些衍生物中，已经评估了5种化合物在人包皮成纤维细胞（HFF）中对正常实验室人巨细胞病毒（HCMV）株AD169的活性。生物测定法表明，在其中的2种含有剩余葡糖胺的化合物中，抗病毒活性中等（化合物9和15，EC 50  = 5.42 µM，CC 50  > 150 µM，SI 50  > 28，EC 50  = 4.91 µM，CC 50  > 150 µM，SI 50 > 31）。这些化合物之间的区别在于，第一种在第4位包含一个邻苯二甲酰亚胺基团，在第5个位置包含磷酰基，而后者在相应的位置上包含一个苯基基团和一个氰基。但是， 在该试验中，它们的活性远远低于对照药物更昔洛韦（EC 50  = 0.32 µM，CC 50  > 150 µM，SI 50 > 476）。这些和先前获得的数据使我们可以考虑将1,3-恶唑用作合成具有抗HCMV活性的新化合物的有前途的骨架。
• A Facile Synthesis of Derivatives of (1,3,4-Thiadiazol-2-yl)glycine and Its Phosphonyl Analogue
  作者：Vladimir S. Brovarets、Aleksandr V. Golovchenko、Stepan G. Pilyo、Alexander N. Chernega、Boris S. Drach

  DOI：10.1055/s-2003-42458

  日期：——

  The adducts formed by 4-functionally-substituted 2-aryl-5-hydrazino-1,3-oxazoles and aryl isothiocyanates recyclize on heating to produce the hitherto unknown derivatives of (1,3,4-thiadiazol-2-yl)glycine and its phosphonyl analogue.

  由 4-功能取代的 2-芳基-5-肼基-1,3-恶唑和芳基异硫氰酸酯形成的加合物在加热时会发生再循环，生成迄今未知的 (1,3,4-thiadiazol-2-yl)glycine 衍生物及其膦酰类似物。
• ——
  作者：S. G. Pil'o

  DOI：10.1023/a:1023333011230

  日期：——

  Enamides of the general formula Cl2C=C(X)NHCOR1, where X = CN, COOAlk, CONH2, P(O)(OEt)(2), P(O)Ph-2, PPh3 Cl-, were treated in succession with alkane- or arenethiols and silver carbonate to obtain 5-alkyl(aryl)thio-2-R-1-4-X-1,3-oxazoles with high selectivity. The latter were converted into the corresponding sulfonyl derivatives. Unlike 2-acylamino-3,3-dichloroacrylonitriles which react with sodium hydrogen sulfide in a nonselective fashion, reactions of derivatives like Cl(ArS)C=C(CN)NHCOR1 with NaHS lead to hitherto unknown 5-arylthio-4-thiocarbamoyl-2-R-1-1,3-oxazoles whose structure was confirmed both by spectral methods and by cyclocondensation with bromoacetophenone according to Hantzsch. Heating of some 2-aryl-5-mercapto-4-X-1,3-oxazoles with benzenethiols results in recyclization into the corresponding 2,4-disubstituted 5-arylthio-1,3-thiazoles, presumably due to prototropic tautomerism in the 5-mercapto-oxazole fragment.
• N-methyl-D-glucamine-derived 4-substituted 1,3-oxazoles
  作者：E. R. Abdurakhmanova、E. I. Lukashuk、A. V. Golovchenko、S. G. Pil’o、V. S. Brovarets

  DOI：10.1134/s1070363215040143

  日期：2015.4

  Reaction of available derivatives of 1-acylamino-2,2-dichloroacrylic acids as well as diethyl esters of 1-acylamino-2,2,2-trichloroethylphosphonic acids with N-methyl-D-glucamine furnished previously unknown 1,3-oxazole derivatives containing nitrile, ester or phosphonyl groups in the position 4 and N-methyl-D-glucamine residue in the position 5.
• Drach,B.S.; Mis'kevich,G.N., Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, p. 2329 - 2333
  作者：Drach,B.S.、Mis'kevich,G.N.

  DOI：——

  日期：——