1,4-bis(4-methoxyphenyl)-3-vinylazetidin-2-one | 109388-01-4

• 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-bis(4-methoxyphenyl)-3-vinylazetidin-2-one
• 英文别名: (3R,4S)-3-ethenyl-1,4-bis(4-methoxyphenyl)azetidin-2-one
• CAS: 109388-01-4
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: ZGFDPRWZAQLZMM-QZTJIDSGSA-N

物化性质

• 熔点：
  77-79 °C
• 沸点：
  530.0±50.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

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：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-bis(4-methoxyphenyl)-3-vinylazetidin-2-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.75h， 以88%的产率得到4-(4-methoxyphenyl)-3-vinylazetidin-2-one
  参考文献：
  名称：

  Argentic oxide mediated N-dearylation of β-lactams

  摘要：

  A method is described for the N-dearylation of N-(4-methoxy- or 4-ethoxyphenyl)-2-azetidinones with argentic oxide. The yields are good-to-excellent and the reaction is simple, efficient, and fast. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.022
• 作为产物：
  描述：

  4-溴-2-丁烯酸甲酯 、 (4-methoxyphenyl)-[1-(4-methoxyphenyl)meth-(E)-ylidene]amine 在 二氯二茂钛 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以77%的产率得到1,4-bis(4-methoxyphenyl)-3-vinylazetidin-2-one
  参考文献：
  名称：

  The synthesis of β-lactams via a one-pot Reformatsky reaction of imines promoted by Zn/Cp2TiCl2 (cat.)

  摘要：

  In the presence of Zn/Cp2TiCl2 (cat.) alpha-bromoacetates, gamma-bromocrotonates or alpha-bromomethylacrylates react with imines in one-pot to form beta-lactams, 3-vinyl-beta-lactams or alpha-methylene-gamma-lactams, respectively, at room temperature without the need for pretreatment of the solvent and Zn. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00187-4

文献信息

• Carbocation catalyzed carboxylic acid activation in Staudinger reaction for stereoselective synthesis of β-lactams
  作者：Ankita Rai、Puneet K. Singh、Prashant Shukla、Vijai K. Rai

  DOI：10.1016/j.tetlet.2016.10.012

  日期：2016.11

  stereoselective β-lactams has been disclosed via cyclopropenium-ion-catalyzed reaction of substituted acetic acids with aldimines under mild conditions. Products are formed in high yields (86–95%) and good diastereoselectivity within 3–4 h. The new reaction is focused on the exploration of the scope of cyclopropenium-ion catalysis and introduction of a catalytic version of one-step Staudinger reaction for β-lactam

  已经公开了通过在温和的条件下环乙酸离子催化的取代乙酸与醛亚胺的合成立体选择性β-内酰胺的新策略。产物在3-4小时内以高收率（86–95％）和良好的非对映选择性形成。该新反应的重点是探索环丙烯离子催化的范围，并引入了用于一步一步Staudinger反应的催化型β-内酰胺合成方法。该反应对于一系列取代的乙酸和醛亚胺是有效的。
• The Vilsmeier reagent: a useful and versatile reagent for the synthesis of 2-azetidinones
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tet.2009.02.005

  日期：2009.4

  and oxalyl chloride or thionyl chloride, works as a versatile acid activator reagent for the direct [2+2] ketene–imine cycloaddition of substituted acetic acid and imines in one-pot synthesis under mild conditions. Monocyclic, spirocyclic and 3-electron-withdrawing group β-lactams were synthesized by this method and optimization of conditions were performed.

  （氯亚甲基）二甲基氯化铵（Vilsmeier试剂），可以轻松地由N，N-二甲基甲酰胺和草酰氯或亚硫酰氯制备，可作为通用的酸活化剂，用于直接[2 + 2]烯酮-亚胺环加成取代的乙酸和亚胺在温和条件下一锅合成。用该方法合成了单环，螺环和3个吸电子基β-内酰胺，并进行了条件优化。
• DMF-dimethyl sulfate as a new reagent for the synthesis of β-lactams
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tetlet.2009.01.092

  日期：2009.4

  alkoxymethylene-N,N-dimethyliminium salts, the adduct formed from DMF and O-alkylating agents. The advantages of this new method are mild reaction conditions, low cost, avoiding the use of chlorinating agents and easy purification of the products. The best results were obtained when DMF and dimethyl sulfate were used at room temperature.

  通过席夫碱，取代的乙酸与烷氧基亚甲基-N，N-二甲基亚胺盐，DMF和O-烷基化剂形成的加合物之间的新型反应，以良好至极佳的产率合成了许多2-氮杂环丁酮。这种新方法的优点是反应条件温和，成本低，避免使用氯化剂和易于纯化产物。当在室温下使用DMF和硫酸二甲酯时，可获得最佳结果。
• 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。
• Sharma, Sain Datt; Anand, Rishi Dev; Kaur, Gurpreet, Journal of Chemical Research, 2005, # 4, p. 248 - 251
  作者：Sharma, Sain Datt、Anand, Rishi Dev、Kaur, Gurpreet

  DOI：——

  日期：——