2-phenyl-5,6-dihydro-[1,4]oxathiine-3-carboxylic acid anilide | 61379-07-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-phenyl-5,6-dihydro-[1,4]oxathiine-3-carboxylic acid anilide
• 英文别名: 1,4-Oxathiin-3-carboxamide, 5,6-dihydro-N,2-diphenyl-；N,6-diphenyl-2,3-dihydro-1,4-oxathiine-5-carboxamide
• CAS: 61379-07-5
• 化学式: C₁₇H₁₅NO₂S
• 分子量: 297.378
• InChiKey: GLNVJEWQUVYAJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-phenyl-5,6-dihydro-[1,4]oxathiine-3-carboxylic acid anilide 在 氯 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-苯甲酰乙酰苯胺
  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

• 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.