methyl 3-(N-allylcarbamoyl)propanoate | 133055-19-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-(N-allylcarbamoyl)propanoate
• 英文别名: Methyl 4-(allylamino)-4-oxobutanoate；methyl 4-oxo-4-(prop-2-enylamino)butanoate
• CAS: 133055-19-3
• 化学式: C₈H₁₃NO₃
• mdl: MFCD19347351
• 分子量: 171.196
• InChiKey: UZAGLMFHNPTIGL-UHFFFAOYSA-N

物化性质

• 沸点：
  325.0±35.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(N-allylcarbamoyl)propanoate 在 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以69%的产率得到methyl 3-cyano-5-hexenoate
  参考文献：
  名称：

  An extremely mild 3-aza-Claisen reaction. 1. Rearrangement of simple N-allylamides.

  摘要：

  An extremely mild 3-aza-Claisen reaction has been developed. Readily available N-allyl amides are converted to pentenylnitriles in moderate to good yields by a transformation that occurs at room temperature under essentially neutral conditions.

  DOI：

  10.1016/0040-4039(91)80848-z
• 作为产物：
  描述：

  丙烯胺 、 丁二酸二甲酯 在 Candida antarctica lipase SP 435 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以95%的产率得到methyl 3-(N-allylcarbamoyl)propanoate
  参考文献：
  名称：

  Selective ammonolysis and aminolysis of dimethyl succinate. Synthesis of optically active N-alkylsuccinimides

  摘要：

  Candida antarctica lipase catalyzes the selective monoammonolysis and aminolysis of dimethyl succinate with ammonia and aliphatic amines, respectively, in dioxane as solvent. This enzyme shows a high enatioselectivity when racemic amines are used. Optically active amidoesters are also obtained in the reaction of dimethyl succinate with racemic alpha-methylalkylamines in hexane as solvent. In this medium, the enzyme catalyzes the formation of N-alkylsuccinimides or optically active N-alkyl-alpha-methylsuccinimides from dimethyl succinate or alpha-methylsuccinate and amines.

  DOI：

  10.1016/0040-4020(94)01043-y

文献信息

• TMSCl Promoted Direct Conversion of Cyclic Anhydrides to (Un)Symmetric‐Diesters/Amide Esters
  作者：Meera Johny、Amuda Manikandan、Goreti Rajendar

  DOI：10.1002/asia.202301017

  日期：2024.2

  A mild, novel, and efficient silyl-promoted conversion of cyclic anhydride to diesters and amide esters. The reaction follows a two-step process, ring opening of anhydride by amine or alcohol following esterification. The reaction was carried out in the presence and absence of base. The method has broad substrate scope and is applicable for the synthesis of commercial plasticizers.

  一种温和、新颖且高效的甲硅烷基促进环酸酐向二酯和酰胺酯的转化。该反应分两步进行，酯化后通过胺或醇使酸酐开环。反应在碱存在和不存在下进行。该方法底物范围广泛，适用于商业增塑剂的合成。
• An extremely mild 3-aza-Claisen reaction. 1. Rearrangement of simple N-allylamides.
  作者：Michael A. Walters、Colleen S. McDonough、Perry S. Brown、Andrew B. Hoem

  DOI：10.1016/0040-4039(91)80848-z

  日期：1991.1

  An extremely mild 3-aza-Claisen reaction has been developed. Readily available N-allyl amides are converted to pentenylnitriles in moderate to good yields by a transformation that occurs at room temperature under essentially neutral conditions.
• Selective ammonolysis and aminolysis of dimethyl succinate. Synthesis of optically active N-alkylsuccinimides
  作者：Susana Puertas、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/0040-4020(94)01043-y

  日期：1995.1

  Candida antarctica lipase catalyzes the selective monoammonolysis and aminolysis of dimethyl succinate with ammonia and aliphatic amines, respectively, in dioxane as solvent. This enzyme shows a high enatioselectivity when racemic amines are used. Optically active amidoesters are also obtained in the reaction of dimethyl succinate with racemic alpha-methylalkylamines in hexane as solvent. In this medium, the enzyme catalyzes the formation of N-alkylsuccinimides or optically active N-alkyl-alpha-methylsuccinimides from dimethyl succinate or alpha-methylsuccinate and amines.
• Rearrangements of Substituted 3-Aza-1,2,5-hexatrienes. 3. The Scope and Versatility of an Extremely Mild 3-Aza-Cope Reaction
  作者：Michael A. Walters、Andrew B. Hoem、Colleen S. McDonough

  DOI：10.1021/jo951587g

  日期：1996.1.1

  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.