N-[(2S,3R,6R,7R)-3-hydroxy-2-(hydroxymethyl)-8-oxo-3-prop-2-enyl-5-thia-1-azabicyclo[4.2.0]octan-7-yl]-2-phenylacetamide | 315206-83-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(2S,3R,6R,7R)-3-hydroxy-2-(hydroxymethyl)-8-oxo-3-prop-2-enyl-5-thia-1-azabicyclo[4.2.0]octan-7-yl]-2-phenylacetamide
• CAS: 315206-83-8
• 化学式: C₁₈H₂₂N₂O₄S
• 分子量: 362.45
• InChiKey: HPLQFSDGQQPGHF-NZPGVSJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,6R,7R)-3-hydroxy-2-(hydroxymethyl)-8-oxo-3-prop-2-enyl-5-thia-1-azabicyclo[4.2.0]octan-7-yl]-2-phenylacetamide 在 甲基磺酰氯 、 三乙胺 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以56%的产率得到N-[(2S,5R,8R,9R)-10-oxo-5-prop-2-enyl-4-oxa-7-thia-1-azatricyclo[6.2.0.02,5]decan-9-yl]-2-phenylacetamide
  参考文献：
  名称：

  Indium and Tin Mediated Allylation Reactions of 3-Hydroxycephem in Aqueous Media

  摘要：

  Allylation of the C-3 position of the cephem nucleus was accomplished by either indium mediated or indium trichloride promoted tin mediated allylation reactions in aqueous media. Both methods gave 3-allyl-3-hydroxycephams 2a similar to 2d, in moderate to excellent yields.

  DOI：

  10.1080/00397910008087052
• 作为产物：
  描述：

  3-羟基头孢 在 indium 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 8.0h， 生成 N-[(2S,3R,6R,7R)-3-hydroxy-2-(hydroxymethyl)-8-oxo-3-prop-2-enyl-5-thia-1-azabicyclo[4.2.0]octan-7-yl]-2-phenylacetamide
  参考文献：
  名称：

  Indium and Tin Mediated Allylation Reactions of 3-Hydroxycephem in Aqueous Media

  摘要：

  Allylation of the C-3 position of the cephem nucleus was accomplished by either indium mediated or indium trichloride promoted tin mediated allylation reactions in aqueous media. Both methods gave 3-allyl-3-hydroxycephams 2a similar to 2d, in moderate to excellent yields.

  DOI：

  10.1080/00397910008087052

文献信息

• Indium and Tin Mediated Allylation Reactions of 3-Hydroxycephem in Aqueous Media
  作者：Jie Eun Lee、Joo Hwan Cha、Ae Nim Pae、Kyung II Choi、Hun Yeong Koh、Youseung Kim、Yong Seo Cho

  DOI：10.1080/00397910008087052

  日期：2000.12

  Allylation of the C-3 position of the cephem nucleus was accomplished by either indium mediated or indium trichloride promoted tin mediated allylation reactions in aqueous media. Both methods gave 3-allyl-3-hydroxycephams 2a similar to 2d, in moderate to excellent yields.