3,3-Dichloro-2-(4-methyl-benzoylamino)-acrylic acid methyl ester | 83990-17-4

• 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: 3,3-Dichloro-2-(4-methyl-benzoylamino)-acrylic acid methyl ester
• 英文别名: Methyl 3,3-dichloro-2-{[(4-methylphenyl)carbonyl]amino}prop-2-enoate；methyl 3,3-dichloro-2-[(4-methylbenzoyl)amino]prop-2-enoate
• CAS: 83990-17-4
• 化学式: C₁₂H₁₁Cl₂NO₃
• 分子量: 288.13
• InChiKey: FQDVCVQZPSZEQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 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：

  3,3-Dichloro-2-(4-methyl-benzoylamino)-acrylic acid methyl ester 在 氯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 60.0h， 生成 methyl 3,3,3-trichloro-2-[(4-methylbenzoyl)imino]propanoate
  参考文献：
  名称：

  三氯丙酮酸N-酰亚胺。与磷亲核试剂的反应

  摘要：

  研究了N-芳酰基三氯乙烷亚胺CCl 3 C（R）= NCOAr（II，R = COOMe，CN）与磷亲核试剂的反应。亚胺II与邻亚苯基二乙基氨基亚磷酸酯的反应以[4 + 1]-环加成进行，导致形成稳定的螺环磷烷。XRD分析证明了其中之一的结构。亚胺II与无环P（III）衍生物[Ph 3 P，Ph 2 POEt，（PhO）3 P]的反应还包括形成不稳定的单环膦烷，该环氧化物消除了氧化膦并进行了变绿转移，从而生成三氯氮二烯CCl 2。＝ C（R）N ＝ C（Cl）Ar。在三乙胺的存在下，亚胺II与（EtO）2 POH的反应导致形成（EtO）2 P（O）Cl和相应的二氯乙烯基酰胺CCl 2 = C（R）NHCOAr。

  DOI：

  10.1134/s1070363212060035

文献信息

• Transformations of Acylation Products of Functionally 4-Substituted 2-Alkyl(aryl)-5-hydrazino-1,3-oxazoles into 1,3,4-Oxadiazole Derivatives
  作者：A. V. Golovchenko、S. G. Pil’o、V. S. Brovarets、A. N. Chernega、B. S. Drach

  DOI：10.1007/s11176-005-0244-8

  日期：2005.3

  Acylation products of 2-aryl-5-hydrazino-4-X-1,3-oxazoles [X = C(O)OAlk, P(O)(OAlk)2], when heated in acetic acid or ethanol, undergo recyclization and transform into the derivatives of 1,3,4-oxadiazol-2-ylglycine or its phosphonyl analog. A similar rearrangement also occurs in the reactions of 2-alkyl(aryl)-5-hydrazino-1,3-oxazole-4-carbonitriles with carboxylic acid chlorides in pyridine, but it is accompanied by additional cyclization involving the amide residue and nitrile group, yielding 2-(5-amino-1,3-oxazol-4-yl)-1,3,4-oxadiazole derivatives.

  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。
• 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。
• Novel Synthetic Approach for N-Acyl Imines of Trichloropyruvate
  作者：Petro Onys'ko、Yaroslav Khomutnyk、Tetyana Kim、Olena Kyselyova、Yuliya Rassukana、Volodymyr Brovarets、Anatoly Synytsya

  DOI：10.1055/s-0030-1258317

  日期：2011.1

  for N-acyl imines of trichloropyruvates [2-(acylimino)-3,3,3-trichloropropanoates] based on consecutive silylation-chlorinative desilylation of readily accessible α-(acylamino)-substituted dichloroacrylates was developed. The use of the 2-iminopropanoates obtained for the amidoalkylation of S-, O-, N-, and C-centered nucleophiles to afford amino acids derivatives is disclosed. N-acyl imines - enamides

  基于容易获得的α-（酰基氨基）-取代的二氯丙烯酸酯的连续甲硅烷基化-氯化甲硅烷基化，开发了三氯丙酮酸酯[2-（酰基酰亚胺）-3,3,3-三氯丙酸酯]的N-酰基亚胺的便捷合成方法。公开了将获得的2-亚氨基丙酸酯用于S-，O-，N-和C-中心亲核体的酰胺烷基化以提供氨基酸衍生物。 N-酰基亚胺-酰胺-亚氨基羧酸酯-三氯甲基-甲硅烷基化-氯化-亲核加成
• Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines
  作者：A. N. Kornienko、S. G. Pil’o、V. M. Prokopenko、V. S. Brovarets

  DOI：10.1134/s1070363214080210

  日期：2014.8

  Previously unknown methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates have been synthesized. Their reactions with amines and amidines have yielded the corresponding sulfonamides and 6H, 7H-[1,3]oxazolo[5,4-d] pyrimidin-7-ones.
• ——
  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.