tert-butyl 5-(2-oxo-4-azetidinyl)-3-oxopentanoate | 141198-19-8

• 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-(2-oxo-4-azetidinyl)-3-oxopentanoate
• 英文别名: 4(R)-4-[4-(t-butyloxycarbonyl)-3-oxobutyl]-azetidin-2-one；t-Butyl 5-(2-oxo-4-azetidinyl)-3-oxopentanoate；4(R)-4-[3-oxo-4-(t-butyloxycarbonyl)butyl]azetidin-2-one；Tert-butyl 3-oxo-5-(4-oxo-2-azetidinyl)pentanoate；tert-butyl 3-oxo-5-(4-oxoazetidin-2-yl)pentanoate
• CAS: 141198-19-8
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: NRVSOFKTBLMWOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-(2-oxo-4-azetidinyl)-3-oxopentanoate 在 4-羧基苯磺叠氮 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 2-Diazo-3-oxo-5-(4-oxo-azetidin-2-yl)-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Functionalization of the .beta.-lactam ring: diastereoselective azide transfer and nitrogen-oxygen bond reduction on C4 substituted N-hydroxy-.beta.-lactams in one step

  摘要：

  DOI：

  10.1021/ja00033a072
• 作为产物：
  描述：

  tert-butyl 5-(1-(benzyloxy)-2-oxo-4-azetidinyl)-3-oxopentanoate 在 palladium on activated charcoal titanium(III) chloride 、 氢气 、 sodium acetate 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 tert-butyl 5-(2-oxo-4-azetidinyl)-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

文献信息

• Process for the preparation of 3-substituted-2-azetidinones
  申请人：UNIVERSITY OF NOTRE DAME

  公开号：EP0564129A2

  公开（公告）日：1993-10-06

  Provided is a process for preparing 3-nucleophile substituted-2-azetidinones by subjecting a N-OR-β-lactam to a nucleophile wherein the 3-substitution is diastereoselective.

  本发明提供了一种通过将 N-OR-β-内酰胺与亲核物作用制备 3-亲核取代的-2-氮杂环丁酮的工艺，其中 3-取代是非对映选择性的。
• Mn(III) promoted N-O bond reduction of N-hydroxy-2-azetidinones
  作者：Arun Ghosh、Marvin J. Miller

  DOI：10.1016/s0040-4039(00)60063-1

  日期：1993.1

  Treatment of various N-hydroxy-2-azetidinones with Mn(III) acetate unexpectedly afforded the corresponding reduced N-unsubstituted-2-azetidinones in the presence of hydrogen donor solvents.
• US5250676A
  申请人：——

  公开号：US5250676A

  公开（公告）日：1993-10-05
• 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
  作者：Catherine M. Gasparski、Arun Ghosh、Marvin J. Miller

  DOI：10.1021/jo00039a009

  日期：1992.6

  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.
• Functionalization of the .beta.-lactam ring: diastereoselective azide transfer and nitrogen-oxygen bond reduction on C4 substituted N-hydroxy-.beta.-lactams in one step
  作者：Catherine M. Gasparski、Min Teng、Marvin J. Miller

  DOI：10.1021/ja00033a072

  日期：1992.3