2,3-dichloro-2-methyl-1,4-oxathiin-3-carboxanilide | 110512-33-9

• 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: 2,3-dichloro-2-methyl-1,4-oxathiin-3-carboxanilide
• 英文别名: 2,3-dichloro-1,4-oxathiane；(2S,3S)-2,3-dichloro-2-methyl-N-phenyl-1,4-oxathiane-3-carboxamide
• CAS: 110512-33-9
• 化学式: C₁₂H₁₃Cl₂NO₂S
• 分子量: 306.213
• InChiKey: WAWUQPNTQJLMJX-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dichloro-2-methyl-1,4-oxathiin-3-carboxanilide 反应 19.0h， 生成 2-chloromethyl-5,6-dihydro-N-phenyl-1,4-oxathiin-3-carboxyamide
  参考文献：
  名称：

  Synthesis of dihydro-1,4-oxathiins by action of chlorine on 1,3-oxathiolanes

  摘要：

  DOI：

  10.1021/jo00233a012
• 作为产物：
  描述：

  萎锈灵 在 氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 2,3-dichloro-2-methyl-1,4-oxathiin-3-carboxanilide
  参考文献：
  名称：

  Conversion of Dihydro-1,4-oxathiin-3-carboxamide to the Isomeric Dihydro-1,4-oxathiin-2-carboxamide

  摘要：

  The preparation of isomeric dihydro-1,4-oxathiin (3) from the dihydro-1,4-oxathiin (1) via dichloro-1,4-oxathiane (4) is described. Chlorination of 1 followed by treatment of the resulting dichloride (4) with aqueous acetone gave dihydroxy-1,4-oxathiin (5). The solvolysis to produce intermediate chlorohydrin (11) was favored relative to elimination reaction to give exomethylene compound (8). Dehydration of 5 followed by reduction afforded alpha-hydroxy-1,3-oxathiolane (2) which is a key compound to prepare the isomeric dihydro-1,4-oxathiin (3). The reason for more facile displacement of chlorine at C-2 in comparison with that at C-3 in 4 was also discussed.

  DOI：

  10.3987/com-94-6944

文献信息

• Formation of Bicyclic b-Lactams from Dichloro-1,4-oxathiane-3-carboxanilides: Nucleophilic Substitution of Nitrogen on Anomeric Carbon
  作者：Hoh-Gyu Hahn、Kee-Hyuk Chang

  DOI：10.3987/com-98-s(h)61

  日期：——

  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.