1-(4-Methoxyphenyl)-4-oxo-3-phenylazetidine-2-carbaldehyde | 888487-52-3

• 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: 1-(4-Methoxyphenyl)-4-oxo-3-phenylazetidine-2-carbaldehyde
• CAS: 888487-52-3
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: UUWPAMKJNUYXKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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-Methoxyphenyl)-4-oxo-3-phenylazetidine-2-carbaldehyde 在 sodium metabisulfite 作用下， 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters

  摘要：

  A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as H-1 NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv strain using BacTiter-Glo (TM) Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with 1050 of less than 15 mu M. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.025
• 作为产物：
  描述：

  2,2-dimethoxyethylidene-4-methyloxyaniline 在 甲酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 1-(4-Methoxyphenyl)-4-oxo-3-phenylazetidine-2-carbaldehyde
  参考文献：
  名称：

  Yb(OTf)₃‐Catalyzed Intermolecular Imino Diels–Alder Reaction of 2‐Azetidinone‐Tethered Aryl Imines as Azadienes

  摘要：

  DOI：

  10.1080/00397910500522157

文献信息

• A novel access to highly functionalised β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction
  作者：Natarajan Arumugam、Jayadevan Jayashankaran、Rathna Durga R.S. Manian、Raghavachary Raghunathan

  DOI：10.1016/j.tet.2005.06.029

  日期：2005.8

  A highly regio- and stereoselective synthesis of novel spiro pyrrolidines/pyrrolizidines containing β-lactam and oxazolone moieties under two different conditions is achieved using [3+2] cycloaddition methodology in moderate to good yield.

  使用[3 + 2]环加成法，可在中等至良好收率下在两种不同条件下实现高度螺线和立体选择性合成新型的含β-内酰胺和恶唑酮部分的螺吡咯烷/吡咯烷核苷。
• Efficient synthesis of <font>β</font>-lactam containing <font>α</font>-hydroxy phosphonates using tartaric acid and fumaric acid as mild catalysts
  作者：Vijaya Bhaskar Vangala、Hari N. Pati

  DOI：10.1080/00397911.2016.1139722

  日期：2016.2.16

  ABSTRACT A short and efficient protocol for the synthesis of β-lactam containing α-hydroxy phosphonate esters using inexpensive catalysts such as tartaric acid and fumaric acid is described. GRAPHICAL ABSTRACT

  摘要描述了一种使用廉价催化剂（如酒石酸和富马酸）合成含有 α-羟基膦酸酯的 β-内酰胺的简短而有效的协议。图形概要
• An efficient one-pot synthesis of tetrahydroquinoline derivatives via an aza Diels–Alder reaction mediated by CAN in an aqueous medium and oxidation to heteroaryl quinolines
  作者：G. Savitha、P.T. Perumal

  DOI：10.1016/j.tetlet.2006.03.046

  日期：2006.5

  Various tetrahydroquinoline derivatives have been synthesized by employing ceric ammonium nitrate in an aqueous medium. Subsequently, the tetrahydroquinolines were oxidized to biheterocycles. (c) 2006 Elsevier Ltd. All rights reserved.
• A New Radical Route to C4-Unsubstituted β-Lactams
  作者：Benito Alcaide、Alberto Rodríguez-Vicente、Miguel A. Sierra

  DOI：10.1016/s0040-4039(97)10476-2

  日期：1998.1

  C4-Unsubstituted beta-lactams 3 are conveniently prepared from easily available 4-formyl-beta-lactams 1, in a sequential three step synthesis, using as the key step a radical reductive decarbonylation of 4-carboxy derivatives through their phenyl selenoesters 2. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters
  作者：Yeong Keng Yoon、Mohamed Ashraf Ali、Ang Chee Wei、Tan Soo Choon、Rusli Ismail

  DOI：10.1016/j.ejmech.2013.06.025

  日期：2015.3

  A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as H-1 NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv strain using BacTiter-Glo (TM) Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with 1050 of less than 15 mu M. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.