(R)-N-(1-苯基乙基)辛酰胺 | 149539-11-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (R)-N-(1-苯基乙基)辛酰胺
• 英文名称: (R)-N-(1-phenylethyl)octanamide
• 英文别名: (R)-N-octanoyl-1-phenylethylamine；N-[(1R)-1-phenylethyl]octanamide
• CAS: 149539-11-7
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: TWXVFDSCHKROSL-CQSZACIVSA-N

物化性质

• 沸点：
  405.2±24.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 (R)-N-(1-苯基乙基)辛酰胺 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以86%的产率得到(R)-N-allyl-N-octanoyl-1-phenylethylamine
  参考文献：
  名称：

  EP1650187

  摘要：

  公开号：
• 作为产物：
  描述：

  辛酸 、 R(+)-alpha-甲基苄胺 在 ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以74%的产率得到(R)-N-(1-苯基乙基)辛酰胺
  参考文献：
  名称：

  XtalFluor-E, an Efficient Coupling Reagent for Amidation of Carboxylic Acids

  摘要：

  Amides were produced from carboxylic acids and amines by using XtalFluor-E as an activator. Even poorly reactive carboxylic acids can be transformed to amides. In addition, optically active amines and/or carboxylic acids were not epimerized/racemized during the process.

  DOI：

  10.1021/ol400045d

文献信息

• Lipase-catalyzed enantioselective reaction of amines with carboxylic acids under reduced pressure in non-solvent system and in ionic liquids
  作者：Roxana Irimescu、Katsuya Kato

  DOI：10.1016/j.tetlet.2003.10.210

  日期：2004.1

  Lipase-catalyzed enantioselective acylation of 1-phenylethylamine and 2-phenyl-1-propylamine was performed by reacting the amines with carboxylic acids in a non-solvent system or in ionic liquids as reaction media. The reaction equilibrium was shifted toward amide synthesis by the removal of formed water under reduced pressure.

  通过在非溶剂体系中或在作为反应介质的离子液体中使胺与羧酸反应，进行了1-苯基乙胺和2-苯基-1-丙胺的脂肪酶催化的对映选择性酰化反应。通过在减压下除去形成的水，使反应平衡向酰胺合成转移。
• Optically active 2-allylcarboxylic acid derivative and process for producing the same
  申请人：Okuro Kazumi

  公开号：US20060223152A1

  公开（公告）日：2006-10-05

  The present invention provides a process for producing an optically active 2-allylcarboxylic acid derivative, which is useful as a pharmaceutical intermediate, from readily available and inexpensive starting materials by the process which can be practiced on a commercial scale in a simple and easy manner, and certain 2-allylcarboxamide derivatives, which are novel and important intermediates in that process. An N-allylcarboxamide derivative undergoes rearrangement reaction diastereoselectively in the presence of a base to give a 2-allylcarboxamide derivative, the resulting derivative is subjected to a carbamation reaction and solvolysis to give an optically active 2-allylcarboxylic acid ester, and then the ester obtained is stereoselectively hydrolyzed using an enzyme to produce 2-allylcarboxylic acid having a high optical purity. In addition, the present invention provides a 2-allylcarboxamide derivative compound which is a novel intermediate in the process of the present invention.

  本发明提供了一种生产光学活性2-烯丙基羧酸衍生物的方法，该衍生物可用作制药中间体，可从易得且廉价的起始材料中通过简单易行的工艺在商业规模上生产，并提供了一些2-烯丙基羧酰胺衍生物，这些衍生物是该过程中的新颖重要中间体。在碱的存在下，N-烯丙基羧酰胺衍生物经历了选择性地重排反应，得到2-烯丙基羧酰胺衍生物，所得衍生物经过碳酸化反应和溶剂解反应，得到光学活性的2-烯丙基羧酸酯，然后使用酶对所得酯进行立体选择性水解，制备具有高光学纯度的2-烯丙基羧酸。此外，本发明还提供了一种2-烯丙基羧酰胺衍生物化合物，该化合物是本发明过程中的新颖中间体。
• OPTICALLY ACTIVE 2-ALLYLCARBOXYLIC ACID DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：KANEKA CORPORATION

  公开号：EP1650187A1

  公开（公告）日：2006-04-26

  The present invention provides a process for producing an optically active 2-allylcarboxylic acid derivative, which is useful as a pharmaceutical intermediate, from readily available and inexpensive starting materials by the process which can be practiced on a commercial scale in a simple and easy manner, and certain 2-allylcarboxamide derivatives, which are novel and important intermediates in that process. An N-allylcarboxamide derivative undergoes rearrangement reaction diastereoselectively in the presence of a base to give a 2-allylcarboxamide derivative, the resulting derivative is subjected to a carbamatiom reaction and solvolysis to give an optically active 2-allylcarboxylic acid ester, and then the ester obtained is stereoselectively hydrolyzed using an enzyme to produce 2-allylcarboxylic acid having a high optical purity. In addition, the present invention provides a 2-allylcarboxamide derivative compound which is a novel intermediate in the process of the present invention.

  本发明提供了一种用容易获得的廉价起始原料生产光学活性 2-烯丙基羧酸衍生物的工艺，该衍生物可作为药物中间体，该工艺可在商业规模上以简单易行的方式实施，本发明还提供了某些 2-烯丙基甲酰胺衍生物，这些衍生物是该工艺中新颖而重要的中间体。 一种 N-烯丙基甲酰胺衍生物在碱存在下发生非对映选择性重排反应，生成 2-烯丙基甲酰胺衍生物，生成的衍生物经过氨基甲酰基反应和溶解反应生成具有光学活性的 2-烯丙基甲酸酯，然后使用酶对生成的酯进行立体选择性水解，生成具有高光学纯度的 2-烯丙基甲酸。此外，本发明还提供了一种 2-烯丙基甲酰胺衍生物化合物，它是本发明工艺中的一种新型中间体。
• US7282605B2
  申请人：——

  公开号：US7282605B2

  公开（公告）日：2007-10-16
• XtalFluor-E, an Efficient Coupling Reagent for Amidation of Carboxylic Acids
  作者：Aurélie Orliac、Domingo Gomez Pardo、Agnès Bombrun、Janine Cossy

  DOI：10.1021/ol400045d

  日期：2013.2.15

  Amides were produced from carboxylic acids and amines by using XtalFluor-E as an activator. Even poorly reactive carboxylic acids can be transformed to amides. In addition, optically active amines and/or carboxylic acids were not epimerized/racemized during the process.