cis-1-(4-Methoxyphenyl)-3-vinyl-4-benzoyl-2-azetidinone | 109387-97-5

• 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: cis-1-(4-Methoxyphenyl)-3-vinyl-4-benzoyl-2-azetidinone
• 英文别名: (3S,4S)-4-benzoyl-3-ethenyl-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 109387-97-5；109387-98-6
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: QNLUMYHKPAXQRS-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  cis-1-(4-Methoxyphenyl)-3-vinyl-4-benzoyl-2-azetidinone 在 cobalt acetylacetonate 苯硅烷 、 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以56%的产率得到4-Hydroxy-6-(4-methoxyphenyl)-2-methyl-4-phenyl-3-oxa-6-azabicyclo<3.2.0>heptane
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylative [2 + 2] Cycloaddition for the Stereoselective Synthesis of Either cis- or trans-3-Alkenyl .beta.-Lactams

  摘要：

  A new potential alkenylketene equivalent, prepared without use of a carboxylic acid or an activated derivative, has been exploited. Palladium-catalyzed carbonylation of an allyl phosphate in the presence of an imine and a tertiary amine under CO pressure (30 kg cm(-2)) stereoselectively gave either a cis-or trans-3-alkenyl beta-lactam in high yield. The stereochemical outcome strongly depends on the nature of the imine employed. Imines conjugated with a carbonyl such as a ketone or an ester stereoselectively produce cis-beta-lactams at room temperature, whereas imines unconjugated with a carbonyl group exclusively afford trans-beta-lactams at 70 degrees C.

  DOI：

  10.1021/jo00090a023
• 作为产物：
  描述：

  磷酸烯丙基二乙酯 、 一氧化碳 、 2-(4-methoxyphenyl)imino-1-phenylethanone 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex N-甲基二环己基胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以58%的产率得到cis-1-(4-Methoxyphenyl)-3-vinyl-4-benzoyl-2-azetidinone
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylative [2 + 2] Cycloaddition for the Stereoselective Synthesis of Either cis- or trans-3-Alkenyl .beta.-Lactams

  摘要：

  A new potential alkenylketene equivalent, prepared without use of a carboxylic acid or an activated derivative, has been exploited. Palladium-catalyzed carbonylation of an allyl phosphate in the presence of an imine and a tertiary amine under CO pressure (30 kg cm(-2)) stereoselectively gave either a cis-or trans-3-alkenyl beta-lactam in high yield. The stereochemical outcome strongly depends on the nature of the imine employed. Imines conjugated with a carbonyl such as a ketone or an ester stereoselectively produce cis-beta-lactams at room temperature, whereas imines unconjugated with a carbonyl group exclusively afford trans-beta-lactams at 70 degrees C.

  DOI：

  10.1021/jo00090a023

文献信息

• A novel chemical transformation of 3-vinyl-4-substituted-2-azetidinones
  作者：Ajay K Bose、Lalitha Krishnan、Dilip R Wagle、Magnar S Manhas

  DOI：10.1016/s0040-4039(00)85371-x

  日期：1986.1

  Transformation of α-vinyl-β-lactams involving an anti-Markovnikov addition reaction is described. The action of PdCl2CuClO2 on the vinyl group leads to terminal aldehydes instead of the expected methyl ketones. The intermediate prepared by the reduction of this aldehyde group followed by conversion of the primary hydroxyl group to a chloro derivative was rearranged in good yield to a 1,2-diaryl-3-car

  描述了涉及抗马尔科夫尼科夫加成反应的α-乙烯基-β-内酰胺的转化。的PdCl的动作2 CuClO 2上的乙烯基通向终端醛而不是预期的甲基酮。通过还原该醛基，然后将伯羟基转化为氯衍生物而制得的中间体以高收率重排为1，2-二芳基-3-羰基甲氧基吡咯烷。