tert-butyl 5-(1-(benzyloxy)-2-oxo-4-azetidinyl)-2--3-oxopentanoate | 141220-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: tert-butyl 5-(1-(benzyloxy)-2-oxo-4-azetidinyl)-2--3-oxopentanoate
• 英文别名: Tert-butyl 2-[4-(dimethylamino)phenyl]imino-3-oxo-5-(4-oxo-1-phenylmethoxyazetidin-2-yl)pentanoate
• CAS: 141220-90-8
• 化学式: C₂₇H₃₃N₃O₅
• 分子量: 479.576
• InChiKey: AQSWFEUHJCYVSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-(1-(benzyloxy)-2-oxo-4-azetidinyl)-2--3-oxopentanoate 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 以70%的产率得到tert-butyl 5-(1-(benzyloxy)-2-oxo-4-azetidinyl)-2,3-dioxopentanoate
  参考文献：
  名称：

  Titanium(III)-mediated synthesis of a 1,2,3-tricarbonyl moiety from an .alpha.-oximido-.beta.-keto ester: application to the synthesis of the carbacephem nucleus

  摘要：

  A general procedure for the conversion of alpha-oximido-beta-keto esters into vicinal tricarbonyl moieties by TiCl3 in aqueous, buffered (pH 5) conditions with acetone cosolvent was demonstrated. As applied to N-hydroxy beta-lactam 17, which contained an alpha-oximido-beta-keto ester side chain, these combined reductive and hydrolytic conditions effected simultaneous tricarbonyl formation and beta-lactam N-O bond reduction. Vicinal tricarbonyl-containing N-unsubstituted beta-lactam 18 was a direct precursor to semifunctionalized carbacephem 1.

  DOI：

  10.1021/jo00039a009
• 作为产物：
  描述：

  tert-butyl 5-(1-(benzyloxy)-2-oxo-4-azetidinyl)-3-oxopentanoate 、 N,N-二甲基-4-亚硝基苯胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以21 mg的产率得到tert-butyl 5-(1-(benzyloxy)-2-oxo-4-azetidinyl)-2--3-oxopentanoate
  参考文献：
  名称：

  Titanium(III)-mediated synthesis of a 1,2,3-tricarbonyl moiety from an .alpha.-oximido-.beta.-keto ester: application to the synthesis of the carbacephem nucleus

  摘要：

  A general procedure for the conversion of alpha-oximido-beta-keto esters into vicinal tricarbonyl moieties by TiCl3 in aqueous, buffered (pH 5) conditions with acetone cosolvent was demonstrated. As applied to N-hydroxy beta-lactam 17, which contained an alpha-oximido-beta-keto ester side chain, these combined reductive and hydrolytic conditions effected simultaneous tricarbonyl formation and beta-lactam N-O bond reduction. Vicinal tricarbonyl-containing N-unsubstituted beta-lactam 18 was a direct precursor to semifunctionalized carbacephem 1.

  DOI：

  10.1021/jo00039a009