5-(1-Hydroxy-4-oxo-azetidin-2-yl)-3-oxo-pentanoic acid tert-butyl ester | 141198-18-7

• 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: 5-(1-Hydroxy-4-oxo-azetidin-2-yl)-3-oxo-pentanoic acid tert-butyl ester
• 英文别名: t-Butyl 5-(1-hydroxy-2-oxo-4-azetidinyl)-3-oxopentanoate；tert-butyl 5-(1-hydroxy-4-oxoazetidin-2-yl)-3-oxopentanoate
• CAS: 141198-18-7
• 化学式: C₁₂H₁₉NO₅
• 分子量: 257.287
• InChiKey: ZBYICJCNVOINDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 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：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(1-Hydroxy-4-oxo-azetidin-2-yl)-3-oxo-pentanoic acid tert-butyl ester 在 titanium(III) chloride 、 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  tert-butyl 5-(1-(benzyloxy)-2-oxo-4-azetidinyl)-3-oxopentanoate 在 钯 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 以to yield t-butyl 5-(1-hydroxy-2-oxo-4-azetidinyl)-3-oxopentanoate (A)的产率得到5-(1-Hydroxy-4-oxo-azetidin-2-yl)-3-oxo-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Process for the preparation of 3-substituted-2-azetidinones

  摘要：

  提供了一种用于对式 ##STR1## 的化合物进行对映选择性制备的过程，其中包括将式 ##STR2## 的化合物置于其阴离子为具有pKa在约-7到约14之间的亲核碱的盐或其硅化衍生物的作用下的步骤；其中，R.sub.1为所述亲核物；R为氢或保护的氨基，R.sub.2为下文所定义的R.sub.4；R.sub.3为离去基；R.sub.4为氢、C.sub.1-C.sub.6烷基或具有式--CH.sub.2--CH.sub.2--R.sub.6的基团，其中R.sub.6为2-呋喃基、萘基、苯基、苯基上选择1、2或3个取自C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6烷氧基、C.sub.1-C.sub.6烷硫基、硝基、卤素、羧基和酰胺的取代基；或R.sub.6为式--COOR.sub.7或--COSR.sub.7的基团，其中R.sub.7选择自C.sub.1-C.sub.6烷基、C.sub.2-C.sub.6烯基、苄基、苯基或苄基或苯基上选择1、2或3个取自C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6烷氧基、C.sub.1-C.sub.6烷硫基、硝基、卤素、羧基和酰胺的取代基；或R.sub.4为式 ##STR3## 的基团，其中L为--OR.sub.7，R.sub.7如上所定义；或R.sub.4为式 ##STR4## 的基团，其中：G为三甲基硅基甲基、氢、C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6取代烷基、苯基或苯基上选择1、2或3个取自C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6烷氧基、C.sub.1-C.sub.6烷硫基、硝基、卤素、羧基和酰胺的取代基。

  公开号：

  US05250676A1

文献信息

• Process for the preparation of 3-substituted-2-azetidinones
  申请人：University of Notre Dame du Lac

  公开号：US05250676A1

  公开（公告）日：1993-10-05

  Provided is a process for diastereoselectively preparing compounds of the formula ##STR1## which includes the step of subjecting a compound of the formula ##STR2## to a salt whose anion is a nucleophilic base whose conjugate acid has a pKa in the range of between about -7 to about 14, or a silylated derivative of the salt; wherein R.sub.1 is said nucleophile; R is hydrogen, or protected amino, R.sub.2 is R.sub.4 as defined herein below; R.sub.3 is a leaving group; and R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or a group of the formula --CH.sub.2 --CH.sub.2 --R.sub.6 wherein R.sub.6 is 2-furyl, naphthyl, phenyl, phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido; or R.sub.6 is a group of the formula --COOR.sub.7 or --COSR.sub.7 in which R.sub.7 is selected from C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, benzyl, phenyl, or benzyl or phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido; or R.sub.4 is a group of the formula ##STR3## wherein L is --OR.sub.7 where R.sub.7 is as defined; or R.sub.4 is a group of the formula ##STR4## wherein: G is trimethylsilylmethyl, hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 substituted alkyl, phenyl, or phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido.

  提供了一种用于对式 ##STR1## 的化合物进行对映选择性制备的过程，其中包括将式 ##STR2## 的化合物置于其阴离子为具有pKa在约-7到约14之间的亲核碱的盐或其硅化衍生物的作用下的步骤；其中，R.sub.1为所述亲核物；R为氢或保护的氨基，R.sub.2为下文所定义的R.sub.4；R.sub.3为离去基；R.sub.4为氢、C.sub.1-C.sub.6烷基或具有式--CH.sub.2--CH.sub.2--R.sub.6的基团，其中R.sub.6为2-呋喃基、萘基、苯基、苯基上选择1、2或3个取自C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6烷氧基、C.sub.1-C.sub.6烷硫基、硝基、卤素、羧基和酰胺的取代基；或R.sub.6为式--COOR.sub.7或--COSR.sub.7的基团，其中R.sub.7选择自C.sub.1-C.sub.6烷基、C.sub.2-C.sub.6烯基、苄基、苯基或苄基或苯基上选择1、2或3个取自C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6烷氧基、C.sub.1-C.sub.6烷硫基、硝基、卤素、羧基和酰胺的取代基；或R.sub.4为式 ##STR3## 的基团，其中L为--OR.sub.7，R.sub.7如上所定义；或R.sub.4为式 ##STR4## 的基团，其中：G为三甲基硅基甲基、氢、C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6取代烷基、苯基或苯基上选择1、2或3个取自C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6烷氧基、C.sub.1-C.sub.6烷硫基、硝基、卤素、羧基和酰胺的取代基。
• 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.
• US5250676A
  申请人：——

  公开号：US5250676A

  公开（公告）日：1993-10-05
• 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.
• 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