5,6-dihydro-N-(2-methoxyphenyl)-2-methyl-1,4-oxathiin-3-carboxamide | 13582-37-1

• 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: 5,6-dihydro-N-(2-methoxyphenyl)-2-methyl-1,4-oxathiin-3-carboxamide
• 英文别名: N-(2-methoxyphenyl)-6-methyl-2,3-dihydro-1,4-oxathiine-5-carboxamide
• CAS: 13582-37-1
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: GHONALNTQUCAEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-N-(2-methoxyphenyl)-2-methyl-1,4-oxathiin-3-carboxamide 在 氯 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1R*,6R*)-1-chloro-7-(2-methoxyphenyl)-6-methyl-5-oxa-2-thia-7-azabicyclo<4,2,0>octan-8-one
  参考文献：
  名称：

  Formation of Bicyclic b-Lactams from Dichloro-1,4-oxathiane-3-carboxanilides: Nucleophilic Substitution of Nitrogen on Anomeric Carbon

  摘要：

  Transformation of dichloro-1,4-oxathiane anilides (2) to bicyclic beta-lactam (5) is described. In the presence of sodium hydride, an intramolecular nucleophilic substitution of nitrogen to anomeric carbon of 2 gave (1R*, 6R*)-1-chloro-6-methyl-7-phenyl-5-oxa-2-thia-7-azabicyclo[4,2,0]octan-8-ones (5). The reason for facile displacement at C-2 is attributable to neighboring group participation of sulfur and C-2 is anomeric. Plausible mechanisms for the formation of 2-chloromethyl-5,6-dihydro-N-phenyl-1,4-oxathiin-3-carboxyamide (4) under the neutral conditions, or 2,3-dihydroxy-2-methyl-N-phenyl-1,4-oxathiane-3-carboxyamide (9) in aqueous solution, or bicyclic beta-lactam (5) in the presence of sodium hydride were proposed.

  DOI：

  10.3987/com-98-s(h)61

文献信息

• Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide
  申请人：UNIROYAL LTD.

  公开号：EP0010843A1

  公开（公告）日：1980-05-14

  A method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide is based on the use of an oxathiolane, namely, 2-methyl-N-phenyl-1,3-oxathilane-2-acetamide, which may be formed by condensing 2-mercaptoethanol with acetoacetanilide under acidic conditions in a solvent medium (aromatic hydrocarbon, chlorinated hydrocarbon or alkyl ester of an aliphatic acid). The said oxathilane, with or without purification, is reacted with hydrogen peroxide in water or in a water-organic solvent mixture under basic conditions in the presence of a catalytic amount of a metal compound such as sodium tungstate to form 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide 3-oxide. The said oxathioiane oxide, while dissolved in a chlorinated hydrocarbon or an alkyl ester of an aliphatic carboxylic acid, or while suspended in an aromatic hydrocarbon, is subjected to a ring expansion reaction by heating under acidic conditions in the presence of a catalytic quantity of an anium compound, i.e., a quaternary ammonium salt or sulfonium, sulfoxonium or phosphonium compound, to form 5,6-dihydro-2-methyt-N-phenyi-1,4-oxathiin-3-carboxamide with evolution of water. The product is a known bactericide and fungicide.

  一种制造 5,6-二氢-2-甲基-N-苯基-1,4-氧硫杂环丁-3-甲酰胺的方法是基于一种氧硫杂环丁烷的使用，即 2-甲基-N-苯基-1,3-氧硫杂环丁烷-2-乙酰胺，它可以由 2-巯基乙醇与乙酰乙酰苯胺在酸性条件下在溶剂介质（芳香烃、氯化烃或脂族酸的烷基酯）中缩合而成。在碱性条件下，在催化量的金属化合物（如钨酸钠）的存在下，在水中或水-有机溶剂混合物中与过氧化氢反应，生成 2-甲基-N-苯基-1,3-氧硫杂环戊烷-2-乙酰胺 3-氧化物。上述氧硫杂环戊烷氧化物溶解在氯化烃或脂肪族羧酸的烷基酯中，或悬浮在芳香烃中，在酸性条件下，在催化量的铵化合物（即）存在下加热，进行扩环反应、季铵盐或锍、砜或鏻化合物，生成 5,6-二氢-2-甲基-N-苯基-1,4-氧硫杂环丁-3-甲酰胺，并有水渗出。该产品是一种已知的杀菌剂和杀真菌剂。
• US4182716A
  申请人：——

  公开号：US4182716A

  公开（公告）日：1980-01-08