N-[4-(3-氧代-3-苯基丙基)苯基]乙酰胺 | 62056-28-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: N-[4-(3-氧代-3-苯基丙基)苯基]乙酰胺
• 英文名称: N-(4-(3-oxo-3-phenylpropyl)phenyl)acetamide
• 英文别名: N-[4-(3-Oxo-3-phenylpropyl)phenyl]acetamide
• CAS: 62056-28-4
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: COKJTJVPSZTLEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：

  N-[4-(3-氧代-3-苯基丙基)苯基]乙酰胺 在 正丁基锂 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-{2-[5-(2-tert-Butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-oxo-2-phenyl-3,6-dihydro-2H-pyran-2-yl]-ethyl}-phenyl)-acetamide
  参考文献：
  名称：

  Nonpeptidic HIV protease inhibitors possessing excellent antiviral activities and therapeutic indices. PD 178390: a lead HIV protease inhibitor

  摘要：

  With the insight generated by the availability of X-ray crystal structures of various 5,6-dihydropyran-2-ones bound to HIV PR, inhibitors possessing various alkyl groups at the 6-position of 5,6-dihydropyran-2-one ring were synthesized. The inhibitors possessing a 6-alkyl group exhibited superior antiviral activities when compared to 6-phenyl analogues. Antiviral efficacies were further improved upon introduction of a polar group (hydroxyl or amino) on the 4-position of the phenethyl moiety as well as the polar group (hydroxymethyl) on the 3-(tert-butyl-5-methyl-phenylthio) moiety. The polar substitution is also advantageous for decreasing toxicity, providing inhibitors with higher therapeutic indices. The best inhibitor among this series, (S)-6-[2-(4-aminophenyl)-ethyl]-(3-(2-tert-butyl-5-methyl-phenylsulfa nyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one (34S), exhibited an EC50 of 200 nM with a therapeutic index of > 1000. More importantly, these non-peptidic inhibitors, 16S and 34S, appear to offer little cross-resistance to the currently marketed peptidomimetic PR inhibitors. The selected inhibitors tested in vitro against mutant HIV PR showed a very small increase in binding affinities relative to wild-type HIV PR. Cmax and absolute bioavailability of 34S were higher and half-life and time above EC95 were longer compared to 16S. Thus 34S, also known as PD 178390, which displays good antiviral efficacy, promising pharmacokinetic characteristics and favorable activity against mutant enzymes and CYP3A4, has been chosen for further preclinical evaluation.

  DOI：

  10.1016/s0968-0896(99)00215-1
• 作为产物：
  描述：

  p-Acetylamino-chalcon 在 甲醇 、 氯化铵 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以84%的产率得到N-[4-(3-氧代-3-苯基丙基)苯基]乙酰胺
  参考文献：
  名称：

  以甲醇和氯化铵为氢源对α，β-不饱和酮进行电化学1,4-还原†

  摘要：

  提出了通过电化学方法可持续的，化学选择性的α，β-不饱和酮的1，4-还原，其中极其廉价的氯化铵（NH 4 Cl）被用作唯一的添加剂。反应在环境温度下在空气中平稳进行。机理研究表明，NH 4 Cl和溶剂甲醇均可作为氢供体。

  DOI：

  10.1039/c9cc02368b

文献信息

• Dihydropyrones with improved antiviral activity
  申请人：Warner-Lambert Company

  公开号：US06046355A1

  公开（公告）日：2000-04-04

  This invention pertains to improved antiviral activity of 6,6-disubstituted-5,6-dihydropyran-2-ones caused by judicious placement of certain polar substituents at the 3 and/or 6 positions. The same substituents which enhance the cellular activity also diminish cytotoxicity further enhancing the desirable properties of these agents as antivirals.

  本发明涉及通过在3和/或6位恰当地放置某些极性取代基，改善6,6-二取代-5,6-二氢吡喃-2-酮的抗病毒活性。这些增强细胞活性的相同取代基还降低了细胞毒性，进一步增强了这些化合物作为抗病毒药物的理想性能。
• Methanol as a hydrogen source: room-temperature highly-selective transfer hydrogenation of α,β-unsaturated ketones
  作者：Nidhi Garg、Hari Prasaad Somasundharam、Pardeep Dahiya、Basker Sundararaju

  DOI：10.1039/d2cc03597a

  日期：——

  The described system offers an ideal, user-friendly protocol for the chemoselective homogeneous hydrogenation of α,β-unsaturated ketones at room temperature using methanol as a liquid organic hydrogen carrier. Excellent yields were achieved with an in situ-prepared phosphine-free Cp*Ir(III)/bipyridonate complex. Chemoselective reduction with other reducible functionalities and late-stage functionalization

  所描述的系统为使用甲醇作为液态有机氢载体在室温下对α、β-不饱和酮进行化学选择性均相氢化提供了一种理想的、用户友好的协议。使用原位制备的无膦Cp*Ir( III )/联吡啶络合物获得了优异的产率。还探索了具有其他可还原功能和后期功能化的化学选择性还原。
• Chemoselective Hydrogenation of α,β-Unsaturated Ketones Catalyzed by a Manganese(I) Hydride Complex
  作者：Kartick Dey、Graham de Ruiter

  DOI：10.1021/acs.orglett.4c00277

  日期：2024.5.24

  Here, we report the chemoselective hydrogenation of α,β-unsaturated ketones catalyzed by a well-defined Mn(I) PCNHCP pincer complex [(PCNHCP)Mn(CO)2H] (1). The reaction is compatible with a wide variety of functional groups that include halides, esters, amides, nitriles, nitro, alkynes, and alkenes, and for most substrates occurs readily at ambient hydrogen pressure (1–2 bar). Mechanistic studies and

  在这里，我们报道了由明确的 Mn(I) PC NHC P 钳配合物 [(PC NHC P)Mn(CO) 2 H] 催化的 α,β-不饱和酮的化学选择性氢化 ( 1 )。该反应与多种官能团兼容，包括卤化物、酯、酰胺、腈、硝基、炔烃和烯烃，并且对于大多数底物来说，在环境氢气压力（1-2 bar）下很容易发生。机理研究和氘标记实验揭示了一种非合作机制，本报告将对此进行进一步讨论。
• DIHYDROPYRONES WITH IMPROVED ANTIVIRAL ACTIVITY
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0935597A2

  公开（公告）日：1999-08-18
• US6046355A
  申请人：——

  公开号：US6046355A

  公开（公告）日：2000-04-04