N-(1-naphthalen-2-ylethyl)-3-phenylpropionamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1-naphthalen-2-ylethyl)-3-phenylpropionamide
• 英文别名: N-(1-naphthalen-2-ylethyl)-3-phenylpropanamide
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: FQWBNIHJIAGAOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  N-(1-naphthalen-2-ylethyl)-3-phenylpropionamide 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以29%的产率得到N-(1-(2-naphthyl)ethyl)-3-phenyl-1-propanamine
  参考文献：
  名称：

  通过酰基琥珀酰亚胺的两步一锅法制备胺。拟钙剂cinacalcet，NPS R-467和NPS R-568的合成

  摘要：

  已经开发了一种通过将衍生自商业上可得的羧酸的酰基琥珀酰亚胺与胺偶联以提供相应的酰胺的方法来制备胺的方法。然后将这些酰胺用氢化二异丁基铝或氢化锂铝原位还原。通过快速色谱纯化后，偶联反应的反应串联，然后还原，得到的胺以相当高的收率收率。这种一锅两反应串联过程已成功地应用于拟钙剂西那卡塞，NPS R-467和NPS R-568的合成。

  DOI：

  10.1016/j.tetlet.2015.05.095
• 作为产物：
  描述：

  反-肉桂酰胺 在 1,1'-双(二苯基膦)二茂铁 、 Wilkinson's catalyst 、 tris(dibenzylideneacetone)dipalladium (0) copper(l) iodide 、 氢气 、 caesium carbonate 、 N,N-二异丙基乙胺 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 反应 18.0h， 生成 N-(1-naphthalen-2-ylethyl)-3-phenylpropionamide
  参考文献：
  名称：

  Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

  摘要：

  Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd-2(dba)(3), 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph3P)(3)RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the alpha-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

  DOI：

  10.1021/jo050669u

文献信息

• Fast and Regioselective Heck Couplings with <i>N</i>-Acyl-<i>N</i>-vinylamine Derivatives
  作者：Anders Lindhardt Hansen、Troels Skrydstrup

  DOI：10.1021/jo050669u

  日期：2005.7.1

  Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd-2(dba)(3), 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph3P)(3)RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the alpha-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.
• A two-step, one pot preparation of amines via acyl succinimides. Synthesis of the calcimimetic agents cinacalcet, NPS R-467, and NPS R-568
  作者：Cassie A. Gooodman、Elise Marie Janci、Olivia Onwodi、Chad C. Simpson、Christopher G. Hamaker、Shawn R. Hitchcock

  DOI：10.1016/j.tetlet.2015.05.095

  日期：2015.7

  affords the amine in fair to good yields after purification by flash chromatography. This one-pot, two reaction tandem process has been successfully applied to the synthesis of the calcimimetic agents cinacalcet, NPS R-467, and NPS R-568.

  已经开发了一种通过将衍生自商业上可得的羧酸的酰基琥珀酰亚胺与胺偶联以提供相应的酰胺的方法来制备胺的方法。然后将这些酰胺用氢化二异丁基铝或氢化锂铝原位还原。通过快速色谱纯化后，偶联反应的反应串联，然后还原，得到的胺以相当高的收率收率。这种一锅两反应串联过程已成功地应用于拟钙剂西那卡塞，NPS R-467和NPS R-568的合成。