N-(((S)-1-(naphthalen-4-yl)propan-2-ylcarbamoyl)methyl)octanamide | 1100754-11-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(((S)-1-(naphthalen-4-yl)propan-2-ylcarbamoyl)methyl)octanamide
• 英文别名: N-(((S)-1-(naphthalen-1-yl)propan-2-ylcarbamoyl)methyl)octanamide；N-[2-[[(2S)-1-naphthalen-1-ylpropan-2-yl]amino]-2-oxoethyl]octanamide
• CAS: 1100754-11-7
• 化学式: C₂₃H₃₂N₂O₂
• 分子量: 368.519
• InChiKey: AOZCVXRAWOXVEH-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2,2-trifluoroethyl 2-(octanamido)acetate 、 (+/-)-1-(1-naphthyl)propan-2-amine 在 alkaline protease 作用下， 以 四氢呋喃 、 3-甲基-3-戊醇 为溶剂， 反应 15.0h， 生成 N-(((S)-1-(naphthalen-4-yl)propan-2-ylcarbamoyl)methyl)octanamide
  参考文献：
  名称：

  En Route to (S)-Selective Chemoenzymatic Dynamic Kinetic Resolution of Aliphatic Amines. One-Pot KR/Racemization/KR Sequence Leading to (S)-Amides

  摘要：

  A one-pot sequential process, involving a radical racemization and an enzymatic resolution, provides access to (S)-amides, from racemic amines, with ee and yields ranging from 78 to 94% and 58 to 80%, respectively.

  DOI：

  10.1021/jo900074w

文献信息

• N-Acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate
  作者：Malek Nechab、Lahssen El Blidi、Nicolas Vanthuyne、Stéphane Gastaldi、Michèle P. Bertrand、Gérard Gil

  DOI：10.1039/b812089g

  日期：——

  Enzymatic kinetic resolution of aliphatic and benzylic amines leading to (S)-amides was achieved by using alkaline protease as the catalyst and N-octanoyl glycine trifluoroethyl ester as the acyl donor; enantioselectivity ranged between 4 to 244, while reaction times were dramatically shortened and ranged between 15 min to 6 h.

  通过使用碱性蛋白酶作为催化剂，N-辛酰基甘氨酸三氟乙基酯作为酰基供体，可以实现脂肪族和苄基胺类的酶动力学拆分，从而生成（S）-酰胺。对映选择性在4至244之间，而反应时间则大大缩短，在15分钟至6小时之间。
• En Route to (<i>S</i>)-Selective Chemoenzymatic Dynamic Kinetic Resolution of Aliphatic Amines. One-Pot KR/Racemization/KR Sequence Leading to (<i>S</i>)-Amides
  作者：Lahssen El Blidi、Malek Nechab、Nicolas Vanthuyne、Stéphane Gastaldi、Michèle P. Bertrand、Gérard Gil

  DOI：10.1021/jo900074w

  日期：2009.4.3

  A one-pot sequential process, involving a radical racemization and an enzymatic resolution, provides access to (S)-amides, from racemic amines, with ee and yields ranging from 78 to 94% and 58 to 80%, respectively.