1-(4-Methoxy-phenyl)-4-((E)-styryl)-azetidine-2,3-dione | 130194-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 1-(4-Methoxy-phenyl)-4-((E)-styryl)-azetidine-2,3-dione
• 英文别名: 1-(4-methoxyphenyl)-4-[(E)-2-phenylethenyl]azetidine-2,3-dione
• CAS: 130194-61-5
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: UJYCDQQAEHEXRL-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-(4-Methoxy-phenyl)-4-((E)-styryl)-azetidine-2,3-dione 、 3-溴丙烯 在 indium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以77%的产率得到(3R,4S)-3-Allyl-3-hydroxy-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one
  参考文献：
  名称：

  Environ-friendly approaches to densely functionalized β-lactams

  摘要：

  A convenient approach to densely functionalized alpha-allyl-beta-lactams has been developed using organometallic reagents and alpha-keto-beta-lactams. Indium mediated Barbier reaction in aqueous media proceeded with a higher level of diastereoselectivity and chemical yield than zinc mediated Barbier reaction in anhydrous organic solvents. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02421-5
• 作为产物：
  描述：

  [1-(4-Methoxy-phenyl)-2-oxo-4-((E)-styryl)-azetidin-3-ylmethyl]-trimethyl-ammonium; iodide 在 sodium periodate 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 8.0h， 生成 1-(4-Methoxy-phenyl)-4-((E)-styryl)-azetidine-2,3-dione
  参考文献：
  名称：

  Preparation of .alpha.-Methylene and .alpha.-Ethylidene .beta.-Lactams via the Ester Enolate-Imine Condensation Using .beta.-(Dialkylamino) Esters as Starting Materials: Scope and Synthetic Applications

  摘要：

  A new, simple procedure for the preparation of appropriately substituted alpha-methylene and alpha-ethylidene beta-lactams via the ester enolate-imine condensation is described. The method is based on the use of lithium 3-(dialkylamino) ester enolates as synthetic equivalents of the corresponding acrylate alpha-anions. Thus, the reaction of lithium enolates of 3-(dialkylamino) esters with imines produced alpha-[(dialkylamino)alkyl] beta-lactams stereoselectively and in high yield. Upon dehydroamination the latter furnished a variety of alpha-alkylidene beta-lactams. The synthesis of 3-alkylidene-4-formyl-2-azetidinones is a particularly significant feature of this work. Preparation of functionalized alpha-keto beta-lactams and beta-lactam-furan hybrids through a dihydroxylation-oxidation process starting from different alpha-alkylidene derivatives is also described. In addition, reduction of various 4-functionalized (Z)- and (E)-3-ethylidene-2-azetidinones yielded the corresponding 3-ethylideneazetidines as advanced precursors of polyoximic acids.

  DOI：

  10.1021/jo00105a013

文献信息

• N,N-Dimethylphosphoramidic dichloride: a convenient reagent for the preparation of β-lactams from acetic acids and imines
  作者：Fernando P Cossío、Iñaki Ganboa、Jesús M García、Begoña Lecea、C Palomo

  DOI：10.1016/s0040-4039(00)96016-7

  日期：1987.1

  A convenient reagent for the preparation of β-lactams from acetic acids and imines is described. A new route to α-keto-β-lactams from 3-bis(ethylthio)β-lactams is also reported. Reaction of 4-acethyl-β-lactams with diazomethane is also made.

  描述了一种用于由乙酸和亚胺制备β-内酰胺的方便试剂。还报道了从3-双（乙硫基）β-内酰胺制备α-酮-β-内酰胺的新途径。还进行了4-乙基-β-内酰胺与重氮甲烷的反应。
• COSSIO, FERNANDO P.;GANBOA, INAKI;GARCIA, JESUS M.;LECEA, BEGONA;PALOMO, +, TETRAHEDRON LETT., 28,(1987) N 17, 1945-1948
  作者：COSSIO, FERNANDO P.、GANBOA, INAKI、GARCIA, JESUS M.、LECEA, BEGONA、PALOMO, +

  DOI：——

  日期：——
• Preparation of .alpha.-Methylene and .alpha.-Ethylidene .beta.-Lactams via the Ester Enolate-Imine Condensation Using .beta.-(Dialkylamino) Esters as Starting Materials: Scope and Synthetic Applications
  作者：Benito Alcaide、Gemma Esteban、Yolanda Martin-Cantalejo、Joaquin Plumet、Julian Rodriguez-Lopez、Angeles Monge、Virginia Perez-Garcia

  DOI：10.1021/jo00105a013

  日期：1994.12

  A new, simple procedure for the preparation of appropriately substituted alpha-methylene and alpha-ethylidene beta-lactams via the ester enolate-imine condensation is described. The method is based on the use of lithium 3-(dialkylamino) ester enolates as synthetic equivalents of the corresponding acrylate alpha-anions. Thus, the reaction of lithium enolates of 3-(dialkylamino) esters with imines produced alpha-[(dialkylamino)alkyl] beta-lactams stereoselectively and in high yield. Upon dehydroamination the latter furnished a variety of alpha-alkylidene beta-lactams. The synthesis of 3-alkylidene-4-formyl-2-azetidinones is a particularly significant feature of this work. Preparation of functionalized alpha-keto beta-lactams and beta-lactam-furan hybrids through a dihydroxylation-oxidation process starting from different alpha-alkylidene derivatives is also described. In addition, reduction of various 4-functionalized (Z)- and (E)-3-ethylidene-2-azetidinones yielded the corresponding 3-ethylideneazetidines as advanced precursors of polyoximic acids.
• Environ-friendly approaches to densely functionalized β-lactams
  作者：M. Jayaraman、Maghar S. Manhas、Ajay K. Bose

  DOI：10.1016/s0040-4039(96)02421-5

  日期：1997.2

  A convenient approach to densely functionalized alpha-allyl-beta-lactams has been developed using organometallic reagents and alpha-keto-beta-lactams. Indium mediated Barbier reaction in aqueous media proceeded with a higher level of diastereoselectivity and chemical yield than zinc mediated Barbier reaction in anhydrous organic solvents. (C) 1997, Elsevier Science Ltd.