(E)-3-ethylidene-4-hydroxymethyl-1-(4-methoxyphenyl)azetidin-2-one | 160947-63-7

• 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: (E)-3-ethylidene-4-hydroxymethyl-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: (3E)-3-ethylidene-4-(hydroxymethyl)-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 160947-63-7
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: VLPCJAKEYQJBTG-QDEBKDIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-ethylidene-4-hydroxymethyl-1-(4-methoxyphenyl)azetidin-2-one 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以65%的产率得到(E)-3-ethylidene-1-(4-methoxyphenyl)azetidin-2-one-4-carboxylic acid
  参考文献：
  名称：

  Neary, Anthony D.; Burke, Catherine M.; O'Leary, Aisling C., Journal of Chemical Research, Miniprint, 2001, p. 501 - 522

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-trans-1-(p-Anisyl)-4-<methyl>-3-<1'-(diisopropylamino)ethyl>azetidin-2-one 在 盐酸 、 sodium tetrahydroborate 、 silica gel 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 49.5h， 生成 (E)-3-ethylidene-4-hydroxymethyl-1-(4-methoxyphenyl)azetidin-2-one
  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

• Neary, Anthony D.; Burke, Catherine M.; O'Leary, Aisling C., Journal of Chemical Research, Miniprint, 2001, p. 501 - 522
  作者：Neary, Anthony D.、Burke, Catherine M.、O'Leary, Aisling C.、Meegan, Mary J.

  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.