2-(1-(4-methoxyphenyl)-2-oxo-4-styrylazetidin-3-yl)isoindoline-1,3-dione

• 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: 2-(1-(4-methoxyphenyl)-2-oxo-4-styrylazetidin-3-yl)isoindoline-1,3-dione
• 英文别名: 1-(4-methoxyphenyl)-3-phthalimido-4-styrylazetidin-2-one；1-p-anisyl-3-phthalimido-4-styrylazetidin-2-one；2-[(3S,4R)-1-(4-methoxyphenyl)-2-oxo-4-(2-phenylethenyl)azetidin-3-yl]isoindole-1,3-dione
• 化学式: C₂₆H₂₀N₂O₄
• 分子量: 424.456
• InChiKey: HHQUFQYWVFTHJV-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 、 在 三光气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到2-(1-(4-methoxyphenyl)-2-oxo-4-styrylazetidin-3-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  Triphosgene, an efficient acid activator for the Staudinger reaction

  摘要：

  An efficient one-step synthesis of beta-lactams by the reaction of imines with acids in the presence of triphosgene and triethylamine has been described. (C) 2000 Elsevier Science: Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02074-2

文献信息

• 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。
• A Mild and Efficient Route to 2-Azetidinones Using the Cyanuric Chloride-DMF Complex
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1055/s-0030-1289517

  日期：2011.10

  Efficient conversion of Schiff bases and carboxylic acids to β-lactams can be carried out at room temperature in CH2Cl2, using a cyanuric chloride-N,N-dimethyl formamide complex. The complex is easily prepared by reaction of cyanuric chloride and DMF, an inexpensive reagent, at room temperature. Optimization of conditions and comparison of yield with cyanuric chloride were performed.

  在室温下，利用氰尿酰氯-N,N-二甲基甲酰胺复合物，可以在CH2Cl2中高效地将席夫碱和羧酸转化为β-内酰胺。通过在室温下将氰尿酰氯与低成本试剂DMF反应，可以轻松制备该复合物。优化了条件并比较了产率与氰尿酰氯的结果。
• 1-Sulfo-2-oxoazetidine derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0053816A1

  公开（公告）日：1982-06-16

  A 1-sulfo-2-oxoazetidine derivative of formula wherein R is a residue derived from an organic compound by removal of one hydrogen atom attached to a carbon atom thereof; R' is an amino group which may optionally be , acylated or protected; X is hydrogen or methoxy, and methods of producing said compound (I) which may be written as follows or wherein the symbols have the same meanings as respectively defined above. The compound (I) has improved antimicrobial and β-lactamase-inhibitory activities and is of value as drugs for human beings and domesticated animals.

  一种 1-磺基-2-氧代氮杂环丁烷衍生物，其式中，R 是有机化合物的残基，通过去除连接到其碳原子上的一个氢原子而得到；R'是氨基，可任选被酰化或保护；X 是氢或甲氧基，以及生产所述化合物 (I) 的方法，其可如下写法或其中的符号分别具有与上述定义相同的含义。 该化合物 (I) 具有更好的抗菌活性和β-内酰胺酶抑制活性，具有作为人类和驯养动物药物的价值。
• Triphosgene, an efficient acid activator for the Staudinger reaction
  作者：D Krishnaswamy、B.M Bhawal、A.R.A.S Deshmukh

  DOI：10.1016/s0040-4039(99)02074-2

  日期：2000.1

  An efficient one-step synthesis of beta-lactams by the reaction of imines with acids in the presence of triphosgene and triethylamine has been described. (C) 2000 Elsevier Science: Ltd. All rights reserved.
• Synthesis of Azetidin-2-Ones from Imines and Acids Using Trichloroacetonitrile-Triphenylphosphine Reagent
  作者：Vidyesh V. Govande、M. Arun、A. R. A. S. Deshmukh、B. M. Bhawal

  DOI：10.1080/00397910008087035

  日期：2000.11

  A one step synthesis of azetidin-2-ones (3a-j) has been described by the reaction of imines (1) with acids (2) in presence of trichloroacetonitrile, triphenylphosphine and triethylamine.