4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)-azetidin-2-one | 68485-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)-azetidin-2-one
• 英文别名: benzyl 4-allyl-2-oxoazetidin-1-yl triphenylphosphoranylideneacetate；4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl) azetidin-2-one；4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one；benzyl 2-(2-oxo-4-prop-2-enylazetidin-1-yl)-2-(triphenyl-λ5-phosphanylidene)acetate
• CAS: 68485-45-0
• 化学式: C₃₃H₃₀NO₃P
• 分子量: 519.58
• InChiKey: YFKOGGQAYGSQAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)-azetidin-2-one 在 臭氧 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 生成 1-<(benzyloxycarbonyl)(triphenylphosphoranylidene)methyl>-2-oxoazetidin-4-ylacetic acid
  参考文献：
  名称：

  橄榄酸类似物。第1部分。7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸酯体系和一些相关的β-内酰胺的全合成

  摘要：

  由五-1,4-二烯和氯磺酰基异氰酸酯制备的4-烯丙基氮杂环丁烷-2-酮已用于合成母体7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸酯体系使用分子内Witting反应来构建2，3-双键的天然低聚酸。衍生自4-烯丙基基团的酮环化生成3-取代的衍生物，同时使用由六-1,5-二烯和氯磺酰基异氰酸酯制得的氮杂环丁烷-2-一已得到同源的8-氧代-1-氮杂双环[4.2] .0]辛-2-烯系统。

  DOI：

  10.1039/p19810003242
• 作为产物：
  描述：

  1,4-戊二烯 在 2,6-二甲基吡啶 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 72.0h， 生成 4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)-azetidin-2-one
  参考文献：
  名称：

  橄榄酸类似物。第1部分。7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸酯体系和一些相关的β-内酰胺的全合成

  摘要：

  由五-1,4-二烯和氯磺酰基异氰酸酯制备的4-烯丙基氮杂环丁烷-2-酮已用于合成母体7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸酯体系使用分子内Witting反应来构建2，3-双键的天然低聚酸。衍生自4-烯丙基基团的酮环化生成3-取代的衍生物，同时使用由六-1,5-二烯和氯磺酰基异氰酸酯制得的氮杂环丁烷-2-一已得到同源的8-氧代-1-氮杂双环[4.2] .0]辛-2-烯系统。

  DOI：

  10.1039/p19810003242

文献信息

• .beta.-Lactam antibacterial agents
  申请人：Beecham Group Limited

  公开号：US04350703A1

  公开（公告）日：1982-09-21

  Compounds are described of the formula (II): ##STR1## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is an ester group; A.sub.1 is a hydrogen atom; and A.sub.2 is a group CR.sub.2 R.sub.3 R.sub.4 wherein R.sub.2 is a hydrogen atom or a hydroxyl group; R.sub.3 is a hydrogen atom or a lower alkyl group; and R.sub.4 is a hydrogen atom or a lower alkyl group, a benzyl group, a phenyl group or is joined to R.sub.3 to form part of a C.sub.5-7 carboxylic ring or is a group of the formula CH(OH)R.sub.5 or CHX wherein R.sub.5 is a hydrogen atom or lower alkyl group and X is an oxygen atom or a CR.sub.6 R.sub.7 group where R.sub.6 is a hydrogen atom or a lower alkyl, phenyl, CN, CO.sub.2 R.sub.8 where R.sub.8 is a lower alkyl, phenyl or benzyl group and R.sub.7 is a hydrogen atom or a lower alkyl group or is joined to R.sub.6 to form part of a C.sub.5-7 carbocyclic ring. These compounds have been found to possess antibacterial properties. The preparation of these compounds is described.

  描述的化合物公式为(II): ##STR1## 其中R1是一个基团，使得CO2R1是一个酯基团；A1是一个氢原子；A2是一个CR2R3R4基团，其中R2是一个氢原子或一个羟基；R3是一个氢原子或一个低级烷基团；R4是一个氢原子或一个低级烷基团、苄基团、苯基团或与R3结合形成一个C5-7羧酸环，或者是一个CH(OH)R5或CHX基团，其中R5是一个氢原子或低级烷基团，X是一个氧原子或一个CR6R7基团，其中R6是一个氢原子或低级烷基、苯基、CN、CO2R8，其中R8是一个低级烷基、苯基或苄基团，R7是一个氢原子或低级烷基团或与R6结合形成一个C5-7碳环。这些化合物具有抗菌性质。这些化合物的制备方法已经描述。
• 4-Allyl azetidinone intermediate for .beta.-lactam antibacterial agents
  申请人：Beecham Group Limited

  公开号：US04401595A1

  公开（公告）日：1983-08-30

  Compounds are provided of the formula (II): ##STR1## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is an ester group and A.sub.1 is a hydrogen atom or a methyl group. These compounds possess antibacterial activity. The preparation of these compounds is described.

  提供以下化合物的公式（II）：##STR1## 其中R₁是一个基团，使得CO₂R₁是一个酯基团，并且A₁是一个氢原子或甲基。这些化合物具有抗菌活性。这些化合物的制备方法如下所述。
• Bicyclic .beta.-lactam antibiotics
  申请人：Beecham Group Limited

  公开号：US04223038A1

  公开（公告）日：1980-09-16

  Compounds of the formula (I): ##STR1## wherein G is hydrogen, alkyl, alkenyl, substituted alkyl or substituted alkenyl, R.sub.1 is alkyl or aryl, substituted alkyl or substituted aryl, and R is an organic group such that --CO.sub.2 R is an ester group are produced. The compounds are useful as antibacterial and .beta.-lactamase inhibitory agents.

  式(I)的化合物：##STR1##其中G是氢，烷基，烯基，取代烷基或取代烯基，R.sub.1是烷基或芳基，取代烷基或取代芳基，R是有机基团，使得--CO.sub.2 R是酯基团。这些化合物可用作抗菌和β-内酰胺酶抑制剂。
• Beta-lactam antibacterial agents
  申请人：Beecham Group Limited

  公开号：US04431587A1

  公开（公告）日：1984-02-14

  Compounds are described of the formula (II): ##STR1## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is an ester group; A.sub.1 is a hydrogen atom; and A.sub.2 is a group CR.sub.2 R.sub.3 R.sub.4 wherein R.sub.2 is a hydrogen atom or a hydroxyl group; R.sub.3 is a hydrogen atom or a lower alkyl group; and R.sub.4 is a hydrogen atom or a lower alkyl group, a benzyl group, a phenyl group or is joined to R.sub.3 to form part of a C.sub.5-7 carboxylic ring or is a group of the formula CH(OH)R.sub.5 or CHX wherein R.sub.5 is a hydrogen atom or lower alkyl group and X is an oxygen atom or a CR.sub.6 R.sub.7 group where R.sub.6 is a hydrogen atom or a lower alkyl, phenyl, CN, CO.sub.2 R.sub.8 where R.sub.8 is a lower alkyl, phenyl or benzyl group and R.sub.7 is a hydrogen atom or a lower alkyl group or is joined to R.sub.6 to form part of a C.sub.5-7 carbocyclic ring. These compounds have been found to possess antibacterial properties. The preparation of these compounds is described.

  化合物的结构式描述为（II）：##STR1## 其中R.sub.1是一个羧酸酯基团（CO.sub.2 R.sub.1）; A.sub.1是氢原子; A.sub.2是一个CR.sub.2 R.sub.3 R.sub.4基团，其中R.sub.2是氢原子或羟基; R.sub.3是氢原子或低碳基基团; R.sub.4是氢原子或低碳基基团、苄基、苯基或与R.sub.3结合形成C.sub.5-7羧基环的一部分，或是一个CH（OH）R.sub.5或CHX的基团，其中R.sub.5是氢原子或低碳基基团，X是氧原子或CR.sub.6 R.sub.7基团，其中R.sub.6是氢原子或低碳基、苯基、CN、CO.sub.2 R.sub.8（其中R.sub.8是低碳基、苯基或苄基），R.sub.7是氢原子或低碳基，或与R.sub.6结合形成C.sub.5-7碳环。这些化合物具有抗菌性能。本文描述了这些化合物的制备方法。
• .beta.-Lactam containing compounds, their preparation and use
  申请人：Beecham Group Limited

  公开号：US04446146A1

  公开（公告）日：1984-05-01

  The compounds of the formula (II): ##STR1## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is a carboxylic acid group or a salt or ester thereof; R.sub.2 is a group of the sub-formula (a) or (b): --CR.sub.4 .dbd.C(R.sub.5) NH.CO.sub.n R.sub.6 (a) --CR.sub.7 .dbd.C(R.sub.8)R.sub.9 (b) wherein R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a lower alkyl group; R.sub.6 is a lower alkyl, phenyl, fluorophenyl, chlorophenyl, bromophenyl or benzyl group; and n is 1 or 2; R.sub.7 is a hydrogen or a lower alkyl group; R.sub.8 is a hydrogen atom or a lower alkyl group; R.sub.9 is a hydrogen atom or a lower alkyl or phenyl group; R.sub.3 is a group of the sub-formula (c): CR.sub.10 R.sub.11 R.sub.12 (c) wherein R.sub.10 is a hydrogen atom or a hydroxyl or O.CO.R.sub.13 or O.CO.OR.sub.13 group where R.sub.13 is a lower alkyl, phenyl, benzyl, fluorobenzyl, chlorobenzyl, bromobenzyl, lower alkoxybenzyl or nitrobenzyl group; R.sub.11 is a hydrogen atom or a lower alkyl group; R.sub.12 is a hydrogen atom or a lower alkyl group; said compounds being in the form of R,S-mixture at C-5: are antibacterial agents. Their use and a process for their preparation is described.

  公式（II）的化合物：##STR1## 其中R.sub.1是一种基团，使得CO.sub.2 R.sub.1是羧酸基团或其盐或酯; R.sub.2是亚式（a）或（b）的基团：--CR.sub.4 .dbd.C（R.sub.5）NH.CO.sub.n R.sub.6（a）--CR.sub.7 .dbd.C（R.sub.8）R.sub.9（b）其中R.sub.4是氢原子或较低的烷基基团; R.sub.5是氢原子或较低的烷基基团; R.sub.6是较低的烷基，苯基，氟苯基，氯苯基，溴苯基或苄基; n为1或2; R.sub.7是氢或较低的烷基基团; R.sub.8是氢原子或较低的烷基基团; R.sub.9是氢原子或较低的烷基或苯基; R.sub.3是亚式（c）的基团：CR.sub.10 R.sub.11 R.sub.12（c）其中R.sub.10是氢原子或羟基或O.CO.R.sub.13或O.CO.OR.sub.13基团，其中R.sub.13是较低的烷基，苯基，苄基，氟苯基，氯苯基，溴苯基，较低的烷氧基苄基或硝基苯基; R.sub.11是氢原子或较低的烷基基团; R.sub.12是氢原子或较低的烷基基团; 这些化合物在C-5处形成R，S混合物：是抗菌剂。描述了它们的用途和制备过程。