N-(4-chlorobenzenesulfonyl)imidoylacetic acid (acetylethoxycarbonyl)methyl ester | 960161-58-4

• 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: N-(4-chlorobenzenesulfonyl)imidoylacetic acid (acetylethoxycarbonyl)methyl ester
• 英文别名: ethyl 2-[N-(p-chlorophenylsulfonyl)acetimidoyloxy]-3-oxo-butanoate；ethyl 2-[(E)-N-(4-chlorophenyl)sulfonyl-C-methylcarbonimidoyl]oxy-3-oxobutanoate
• CAS: 960161-58-4
• 化学式: C₁₄H₁₆ClNO₆S
• 分子量: 361.803
• InChiKey: WVTQWRWBUBTNRF-MHWRWJLKSA-N

物化性质

• 沸点：
  470.8±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(4-chlorobenzenesulfonyl)imidoylacetic acid (acetylethoxycarbonyl)methyl ester 以 甲醇 为溶剂， 反应 5.0h， 以58%的产率得到4-氯苯磺酰胺
  参考文献：
  名称：

  Chemistry of diazocarbonyl compounds: XXVIII. Reaction of acyclic N-arylsulfonylacetamides with Rh(II)-carbenoids as a new synthetic route to alkyl acetimidoates

  摘要：

  A new procedure was proposed for the synthesis of alkyl acetimidoates via alkylation of the carbonyl group in N-arylsulfonylacetamides with Rh(II)-carbenoids. The procedure ensures preparation in good yield of acetimidoates having a polyfunctionalized O-alkyl group. The obtained alkyl acetimidoates in crystal exist as E isomers with respect to the C=N bond and as s-cis conformers relative to the C-OCHRR' bond. Alkyl N-arylsulfonylacetimidoates react with ammonia and hydrazine hydrate to give in good yield the corresponding carboximidamides(hydrazides) via replacement of the O-alkyl group. Unlike structurally related compounds having simple alkyl or aryl groups on the nitrogen atom, N-arylsulfonylacetimidoates readily undergo hydrolysis in the presence of moisture and traces of acids.

  DOI：

  10.1134/s1070428006120074
• 作为产物：
  描述：

  重氮基乙酰乙酸乙酯 、 N-((4-chlorophenyl)sulfonyl)acetamide 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到N-(4-chlorobenzenesulfonyl)imidoylacetic acid (acetylethoxycarbonyl)methyl ester
  参考文献：
  名称：

  与Rh（II）-酮类化合物反应的环状和无环磺酰亚胺：酰亚胺基羰基化学选择性O-官能化的新途径。

  摘要：

  在异噻唑-3（2H）-1,1-二氧化物和许多N-（芳磺酰基）甲酰胺在二氯甲烷或二氯乙烷溶液中的存在下，使用四乙酸dirhodium催化重氮乙酰丙酮，重氮乙酰乙酸，重氮丙二酸和重氮乙酸酯的催化分解，得到Rh（II）-类胡萝卜素使亚胺基羰基的O-烷基化，并最终形成O-烷基亚氨酸盐。该反应通过羰基化物以高化学选择性进行，并为以高收率得到具有多官能O-烷基的酰亚胺化物提供了强有力的合成方法。根据X射线分析以及1H-和13C-NMR研究表明，所得的无环O-烷基亚氨酸盐在固态和溶液中均具有E-构型。与无环类似物不同

  DOI：

  10.1039/b508317f

文献信息

• Cyclic and acyclic sulfonimides in reactions with Rh(ii)-ketocarbenoids: a new access to chemoselective O-functionalization of the imidic carbonyl groups
  作者：Vsevolod Nikolaev、Lothar Hennig、Jochim Sieler、Ludmila Rodina、Barbel Schulze、Valerij Nikolaev

  DOI：10.1039/b508317f

  日期：——

  diazomalonic, and diazoacetic esters using dirhodium tetraacetate in the presence of isothiazol-3(2H)-one 1,1-dioxides and a number of N-(arenesulfonyl)carboxamides in solutions of methylene chloride or dichloroethane gives rise to O-alkylation of the imidic carbonyl groups by Rh(II)-carbenoids and the formation of O-alkylimidates as the final products. The reaction proceeds with high chemoselectivity via

  在异噻唑-3（2H）-1,1-二氧化物和许多N-（芳磺酰基）甲酰胺在二氯甲烷或二氯乙烷溶液中的存在下，使用四乙酸dirhodium催化重氮乙酰丙酮，重氮乙酰乙酸，重氮丙二酸和重氮乙酸酯的催化分解，得到Rh（II）-类胡萝卜素使亚胺基羰基的O-烷基化，并最终形成O-烷基亚氨酸盐。该反应通过羰基化物以高化学选择性进行，并为以高收率得到具有多官能O-烷基的酰亚胺化物提供了强有力的合成方法。根据X射线分析以及1H-和13C-NMR研究表明，所得的无环O-烷基亚氨酸盐在固态和溶液中均具有E-构型。与无环类似物不同
• Chemistry of diazocarbonyl compounds: XXVIII. Reaction of acyclic N-arylsulfonylacetamides with Rh(II)-carbenoids as a new synthetic route to alkyl acetimidoates
  作者：A. V. Selivanova、V. V. Nikolaev、R. R. Kostikov、V. A. Nikolaev、J. Siler、B. Schulze

  DOI：10.1134/s1070428006120074

  日期：2006.12

  A new procedure was proposed for the synthesis of alkyl acetimidoates via alkylation of the carbonyl group in N-arylsulfonylacetamides with Rh(II)-carbenoids. The procedure ensures preparation in good yield of acetimidoates having a polyfunctionalized O-alkyl group. The obtained alkyl acetimidoates in crystal exist as E isomers with respect to the C=N bond and as s-cis conformers relative to the C-OCHRR' bond. Alkyl N-arylsulfonylacetimidoates react with ammonia and hydrazine hydrate to give in good yield the corresponding carboximidamides(hydrazides) via replacement of the O-alkyl group. Unlike structurally related compounds having simple alkyl or aryl groups on the nitrogen atom, N-arylsulfonylacetimidoates readily undergo hydrolysis in the presence of moisture and traces of acids.