3-methylidene-4-phenyl-2-azetidinone | 129544-55-4

• 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: 3-methylidene-4-phenyl-2-azetidinone
• 英文别名: 1-(4-Methoxyphenyl)-3-methylidene-4-phenylazetidin-2-one
• CAS: 129544-55-4
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: FWIXOSIGKCPDCH-UHFFFAOYSA-N

物化性质

• 沸点：
  415.3±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylidene-4-phenyl-2-azetidinone 在 sodium periodate 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 、 碳酸氢钠 、 氯化铵 、 镉 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 α-[(4-methoxyphenyl)amino]benzeneacetic acid
  参考文献：
  名称：

  A Novel One-Step Approach for the Preparation of α-Amino Acids, α-Amino Amides, and Dipeptides from Azetidine-2,3-diones

  摘要：

  A remarkable reaction of azetidine-2,3-diones with primary as well as secondary amines, and water is presented. Simply by varying the nucleophile, an unprecedented one-step synthesis of alpha-amino acids, alpha-amino amides, and dipeptides, was developed in both the racemic and optically pure forms. The current mechanistic hypothesis invokes a concerted process involving CO extrusion. However, a stepwise pathway can also account for these novel transformations.

  DOI：

  10.1002/1521-3765(20020816)8:16<3646::aid-chem3646>3.0.co;2-m
• 作为产物：
  描述：

  3-[(Dimethylamino)methyl]-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 16.0h， 生成 3-methylidene-4-phenyl-2-azetidinone
  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

• Thieme Chemistry Journals Awardees – Where Are They Now? Stereoselective Cycloaddition of 2,2,2-Trifluorodiazoethane with α-Methylene-β-lactams: Facile Synthesis of Trifluoromethyl-Substituted Spirocyclic β-Lactams
  作者：Jun-An Ma、Shen Li、Wen-Jie Cao

  DOI：10.1055/s-0036-1588363

  日期：——

  The cycloadditions of 2,2,2-trifluorodiazoethane with α-methylene-β-lactams were investigated. The reaction proceeded via a [3+2] cycloaddition mode under metal-free conditions, whereas the use of an iron catalyst enabled a cyclopropanation to occur. This protocol offers a facile access to a broad range of trifluoromethyl containing spirocyclic β-lactams.

  研究了 2,2,2-三氟重氮乙烷与 α-亚甲基-β-内酰胺的环加成反应。该反应在无金属条件下通过 [3+2] 环加成模式进行，而铁催化剂的使用能够发生环丙烷化。该协议提供了对各种含三氟甲基的螺环 β-内酰胺的轻松访问。
• A novel synthetic approach to α-alkylidene-α-lactams
  作者：Benito Alcaide、Joaquin Plumet、Julián Rodríguez-López、Yolanda M. Sánchez-Cantalejo

  DOI：10.1016/s0040-4039(00)97398-2

  日期：1990.1