Phthalimidoacetic acid allylamide | 74169-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: Phthalimidoacetic acid allylamide
• 英文别名: N-allyl-2-phthalylacetamide；N-Allyl-2-(1,3-dioxoisoindolin-2-yl)acetamide；2-(1,3-dioxoisoindol-2-yl)-N-prop-2-enylacetamide
• CAS: 74169-73-6
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: YFQAAIRXDMUCAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Phthalimidoacetic acid allylamide 在 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 乙腈 为溶剂， 以78%的产率得到2-phthalyl-4-pentenenitrile
  参考文献：
  名称：

  极温和的3-氮杂-claisen反应。2.α-杂原子取代酰胺的新条件和重排

  摘要：

  已经开发出几种新的和潜在有用的N-烯丙基酰胺的3-氮杂-克莱森重排反应条件。这些新条件已成功地应用于形成α-氨基腈和受保护的氰醇的α-杂原子取代物种的重排。

  DOI：

  10.1016/s0040-4039(00)60316-7
• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 生成 Phthalimidoacetic acid allylamide
  参考文献：
  名称：

  Rearrangements of Substituted 3-Aza-1,2,5-hexatrienes. 3. The Scope and Versatility of an Extremely Mild 3-Aza-Cope Reaction

  摘要：

  An investigation of the [3,3]-sigmatropic reaction of substituted 3-aza-1,2,5-hexatrienes to give 4-pentenenitriles is presented. This reaction has been found to occur under a wide variety of reactions conditions (10 are reported) starting from readily available N-allylamides. In contrast to other 3-aza-Cope reactions, this process occurs at room temperature, under essentially neutral conditions, allowing for the facile preparation of substituted nitrile products in moderate to excellent yields. The scope and versatility of this reaction are demonstrated by its use on a wide variety of substrates, including nitrogen- and oxygen-substituted amides. The rearrangements of cis- and trans-4-tert-butyl-N-allylcyclohexanecarboxamides 16a and 16b are reported and were found to give a ratio of axial to equatorial (A:E) products consistent with A:E ratios found for other related sigmatropic reactions. The stereochemical requirements for this reaction appear to be similar to other [3,3]-rearrangements even though the transition state for this rearrangement is most likely neither boat nor chairlike.

  DOI：

  10.1021/jo951587g

文献信息

• An extremely mild 3-aza-claisen reaction. 2. New conditions and the rearrangement of α-heteroatom substituted amides
  作者：M.A. Walters、A.B. Hoem、H.R. Arcand、A.D. Hegeman、C.S. McDonough

  DOI：10.1016/s0040-4039(00)60316-7

  日期：1993.2

  Several new and potentially useful reaction conditions for the 3-aza-Claisen rearrangement of N-allyl amides have been developed. These new conditions have been successfully applied to the rearrangement of α-heteroatom substituted species forming α-amino nitriles and protected cyanohydrins as products.

  已经开发出几种新的和潜在有用的N-烯丙基酰胺的3-氮杂-克莱森重排反应条件。这些新条件已成功地应用于形成α-氨基腈和受保护的氰醇的α-杂原子取代物种的重排。
• METHOD FOR SYNTHESIZING ONE-DIMENSIONAL HELICAL NANOPOROUS STRUCTURES AND METHOD FOR SYNTHESIZING GLYCINE-DERIVED SURFACTANT FOR SYNTHESIZING HELICAL NANOPOROUS STRUCTURES
  申请人：Han Sang Cheol

  公开号：US20110039682A1

  公开（公告）日：2011-02-17

  Disclosed herein are a method for synthesizing one-dimensional helical mesoporous structure, in which a self-assembled structure of a glycine-derived surfactant is used as a template at room temperature to synthesize the one-dimensional helical mesoporous silica structures having a uniform pore size and a method for synthesizing a glycine-derived surfactant for synthesizing the helical nanoporous structures, in which relatively expensive surfactant can be easily recovered using an organic solvent and reused, which provides economical and environment friendly effects and the glycine-derived surfactant is synthesized by homogeneously heating a reaction product of glycine and phthalic anhydride by dielectric heating with irradiation of microwave, whereby it is possible to realize high yield of the glycine-derived surfactant, shortened synthesis time and increase in energy efficiency, leading to improvement in productivity and reduction in production cost.

  本文公开了一种合成一维螺旋介孔结构的方法，该方法利用甘氨酸衍生的表面活性剂的自组装结构作为模板，在室温下合成具有均匀孔径的一维螺旋介孔二氧化硅结构。同时，本文还公开了一种合成甘氨酸衍生表面活性剂的方法，该方法可以使用有机溶剂轻松回收并重复使用相对昂贵的表面活性剂，从而实现经济和环境友好的效果。甘氨酸衍生表面活性剂是通过将甘氨酸和邻苯二甲酸酐的反应产物在介电加热和微波辐射下均匀加热而合成的，从而可以实现高产率的甘氨酸衍生表面活性剂、缩短合成时间和提高能源效率，从而提高生产效率并降低生产成本。
• Synthesis and biological activity of amides of ω-(phthalimido)-alkyl carboxylic acids
  作者：Yu. S. Andreichikov、V. V. Zalesov、N. A. Podushkina

  DOI：10.1007/bf00765906

  日期：1980.2
• US8435480B2
  申请人：——

  公开号：US8435480B2

  公开（公告）日：2013-05-07
• [EN] METHOD FOR SYNTHESIZING ONE-DIMENSIONAL HELICAL NANOPOROUS STRUCTURES AND METHOD FOR SYNTHESIZING GLYCINE-DERIVED SURFACTANT FOR SYNTHESIZING HELICAL NANOPOROUS STRUCTURES<br/>[FR] PROCÉDÉ POUR SYNTHÉTISER DES STRUCTURES NANOPOREUSES HÉLICOÏDALES UNIDIMENSIONNELLE ET PROCÉDÉ POUR SYNTHÉTISER UN TENSIO-ACTIF DÉRIVÉ DE LA GLYCINE SERVANT À LA SYNTHÈSE DES STRUCTURES NANOPOREUSES HÉLICOÏDALES
  申请人：THERMOLON KOREA CO LTD

  公开号：WO2009131324A2

  公开（公告）日：2009-10-29

  Disclosed herein are a method for synthesizing one-dimensional helical mesoporous structure, in which a self-assembled structure of a glycine-derived surfactant is used as a template at room temperature to synthesize the one-dimensional helical mesoporous silica structures having a uniform pore size and a method for synthesizing a glycine-derived surfactant for synthesizing the helical nanoporous structures, in which relatively expensive surfactant can be easily recovered using an organic solvent and reused, which provides economical and environment friendly effects and the glycine-derived surfactant is synthesized by homogeneously heating a reaction product of glycine and phthalic anhydride by dielectric heating with irradiation of microwave, whereby it is possible to realize high yield of the glycine-derived surfactant, shortened synthesis time and increase in energy efficiency, leading to improvement in productivity and reduction in production cost.