(R)-(+)-N-(1-phenylethyl)-3-oxo-3-phenylpropionamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-N-(1-phenylethyl)-3-oxo-3-phenylpropionamide
• 英文别名: 3-oxo-3-phenyl-N-((R)-1-phenylethyl)propanamide；3-oxo-3-phenyl-N-[(R)-1-phenylethyl]propanamide；3-oxo-3-phenyl-N-[(1R)-1-phenylethyl]propanamide
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: CRPFFFMQMYEZEY-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(+)-N-(1-phenylethyl)-3-oxo-3-phenylpropionamide 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 0.03h， 以12%的产率得到
  参考文献：
  名称：

  Synthesis of enantiopure β-amino amides via a practical reductive amination of the corresponding β-keto amides

  摘要：

  A convenient and efficient reductive amination for the preparation of chiral beta-amino amides is developed utilizing microwave heating. A variety of chiral beta-keto amides react with ammonium acetate and sodium cyanoborohydride to afford the desired functionalized amines in good yields. This improved procedure takes advantage of microwave heating to significantly accelerate the reaction and offers a convenient and effective method to access some interesting molecules containing primary amine functionalities. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.111
• 作为产物：
  描述：

  苯乙酮 在 sodium hydride 作用下， 以 甲苯 为溶剂， 生成 (R)-(+)-N-(1-phenylethyl)-3-oxo-3-phenylpropionamide
  参考文献：
  名称：

  Synthesis of enantiopure β-amino amides via a practical reductive amination of the corresponding β-keto amides

  摘要：

  A convenient and efficient reductive amination for the preparation of chiral beta-amino amides is developed utilizing microwave heating. A variety of chiral beta-keto amides react with ammonium acetate and sodium cyanoborohydride to afford the desired functionalized amines in good yields. This improved procedure takes advantage of microwave heating to significantly accelerate the reaction and offers a convenient and effective method to access some interesting molecules containing primary amine functionalities. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.111

文献信息

• Selective exploitation of acetoacetate carbonyl groups using imidazolium based ionic liquids: synthesis of 3-oxo-amides and substituted benzimidazoles
  作者：Ankita Chakraborty、Swapan Majumdar、Dilip K. Maiti

  DOI：10.1016/j.tetlet.2016.06.048

  日期：2016.7

  An unprecedented Brønsted base ionic liquid tuned selective aminolysis of ester carbonyl of acetoacetates is demonstrated to achieve acetoacetamide derivatives. Other imidazolium ionic liquid performs an efficient cyclization catalysis involving acetoacetate-carbonyl groups and o-phenylenediamine at elevated temperature to produce benzimidazoles via C–C bond cleavage of intermediate 1,5-benzodiazepinones

  证明了空前的Brønsted碱性离子液体对乙酰乙酸酯的羰基酯进行选择性氨解，可以实现乙酰乙酰胺衍生物。其他咪唑鎓离子液体可在高温下通过乙酰乙酸酯羰基和邻苯二胺进行高效环化催化，以在无溶剂条件下通过中间体1,5-苯并二氮杂酮的C-C键裂解生成苯并咪唑。
• Lipase-catalyzed aminolysis and ammonolysis of β-ketoesters. Synthesis of optically active β-ketoamides.
  作者：María Jesús García、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/s0040-4020(01)81346-6

  日期：1994.1

  Aminolysis and ammonolysis reactions of β-ketoesters catalysed by Candida antarctica lipase are very efficient methods for the preparation of β—ketoamides. When racemic amines are used in these processes, the corresponding optically active β—ketoamides are obtained with moderate-high enantiomeric excesses.

  南极假丝酵母脂肪酶催化的β-酮酯的氨解和氨解反应是制备β-酮酰胺的非常有效的方法。当在这些方法中使用外消旋胺时，可获得具有适度高对映体过量的相应旋光性β-酮酰胺。
• Garcia Maria Jesus, Rebolledo Francisca, Gotor Vicente, Tetrahedron, 50 (1994) N 23, S 6935-6940
  作者：Garcia Maria Jesus, Rebolledo Francisca, Gotor Vicente

  DOI：——

  日期：——
• Synthesis of enantiopure β-amino amides via a practical reductive amination of the corresponding β-keto amides
  作者：Dalila Mtat、Ridha Touati、Béchir Ben Hassine

  DOI：10.1016/j.tetlet.2014.09.111

  日期：2014.11

  A convenient and efficient reductive amination for the preparation of chiral beta-amino amides is developed utilizing microwave heating. A variety of chiral beta-keto amides react with ammonium acetate and sodium cyanoborohydride to afford the desired functionalized amines in good yields. This improved procedure takes advantage of microwave heating to significantly accelerate the reaction and offers a convenient and effective method to access some interesting molecules containing primary amine functionalities. (C) 2014 Elsevier Ltd. All rights reserved.