N-benzyl-2-(4-isobutylphenyl)-N-acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-2-(4-isobutylphenyl)-N-acetamide
• 英文别名: N-benzyl-2-[4-(2-methylpropyl)phenyl]acetamide
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: ABJIFDMAQGSGQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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-benzyl-2-(4-isobutylphenyl)-N-acetamide 、 4-tert-butoxy-2-isopropoxy-7-(R)-oxiranyl-benzothiazole 在 二异丁基氢化铝 作用下， 以 甲苯 、 正丁醇 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1-hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist

  摘要：

  The optimisation of two series of 4-hydroxybenzothiazolone derived β2-adrenoceptor agonists, bearing α-substituted cyclopentyl and β-phenethyl amino-substituents, as inhaled long-acting bronchodilators is described. Analogues were selected for synthesis using a lipophilicity based hypothesis to achieve the targeted rapid onset of action in combination with a long duration of action. The profiling of the two series led to identification of the α-substituted cyclopentyl analogue 2 as the optimal compound with a comparable profile to the inhaled once-daily long-acting β2-adrenoceptor agonist indacaterol. On the basis of these data 2 was promoted as the backup development candidate to indacaterol from the Novartis LABA project.

  DOI：

  10.1016/j.bmcl.2014.06.014
• 作为产物：
  描述：

  异丁芬酸 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 20.5h， 生成 N-benzyl-2-(4-isobutylphenyl)-N-acetamide
  参考文献：
  名称：

  N-酰基三氟甲烷磺酰胺作为脂族和芳族胺的新型化学选择性酰化剂

  摘要：

  这项工作描述了N-酰基磺酰胺类铵盐内部缩合的研究进展。N-酰基三氟甲烷磺酰胺由于其较高的反应性和酸度而显示出优于非氟化类似物的显着优点。已使用多种胺研究了反应的化学选择性。反应对空间效应和电子效应的敏感性证实了这些试剂在多胺化学选择性酰化中的潜在应用。

  DOI：

  10.1016/j.tet.2006.03.097

文献信息

• N-Acyltrifluoromethanesulfonamides as new chemoselective acylating agents for aliphatic and aromatic amines
  作者：Sophie Guillard、Andrea Aramini、Maria C. Cesta、Sandro Colagioia、Silvia Coniglio、Filippo Genovese、Giuseppe Nano、Emanuela Nuzzo、Valerie Orlando、Marcello Allegretti

  DOI：10.1016/j.tet.2006.03.097

  日期：2006.6

  N-Acyltrifluoromethanesulfonamides show considerable advantages over the non fluorinated analogues by virtue of their higher reactivity and acidity. The reaction chemoselectivity has been investigated using a wide range of amines. The sensitivity of the reaction to steric and electronic effects confirms the potential application of these reagents in chemoselective acylation of polyamines.

  这项工作描述了N-酰基磺酰胺类铵盐内部缩合的研究进展。N-酰基三氟甲烷磺酰胺由于其较高的反应性和酸度而显示出优于非氟化类似物的显着优点。已使用多种胺研究了反应的化学选择性。反应对空间效应和电子效应的敏感性证实了这些试剂在多胺化学选择性酰化中的潜在应用。
• The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1-hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist
  作者：Nicola Arnold、David Beattie、Michelle Bradley、Andrew Brearley、Lyndon Brown、Steven J. Charlton、Robin A. Fairhurst、David Farr、John Fozard、Joe Fullerton、Martin Gosling、Julia Hatto、Diana Janus、Darryl Jones、Lynne Jordan、Christine Lewis、Janet Maas、Clive McCarthy、Mark Mercer、Helen Oakman、Neil Press、Rachel Profit、Friedrich Schuerch、David Sykes、Roger J. Taylor、Alexandre Trifilieff、Andrew Tuffnell

  DOI：10.1016/j.bmcl.2014.06.014

  日期：2014.9

  The optimisation of two series of 4-hydroxybenzothiazolone derived β2-adrenoceptor agonists, bearing α-substituted cyclopentyl and β-phenethyl amino-substituents, as inhaled long-acting bronchodilators is described. Analogues were selected for synthesis using a lipophilicity based hypothesis to achieve the targeted rapid onset of action in combination with a long duration of action. The profiling of the two series led to identification of the α-substituted cyclopentyl analogue 2 as the optimal compound with a comparable profile to the inhaled once-daily long-acting β2-adrenoceptor agonist indacaterol. On the basis of these data 2 was promoted as the backup development candidate to indacaterol from the Novartis LABA project.