(E)-N-(3-(benzylamino)-3-oxoprop-1-enyl)benzamide | 852700-51-7

• 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: (E)-N-(3-(benzylamino)-3-oxoprop-1-enyl)benzamide
• 英文别名: N-[(1E)-3-Oxo-3-[(phenylmethyl)amino]-1-propen-1-yl]benzamide；N-[(E)-3-(benzylamino)-3-oxoprop-1-enyl]benzamide
• CAS: 852700-51-7
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: UWRYWMAQHAQOKF-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-3-Benzoylamino-acrylic acid allyl ester 在 2,6-二甲基吡啶 、 四(三苯基膦)钯 、 chloro-1,1,3,3-tetramethyluronium hexachloro-antimonate 、 polymer supported N-hydroxyphthalimide 、 PS-HOBt 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (E)-N-(3-(benzylamino)-3-oxoprop-1-enyl)benzamide
  参考文献：
  名称：

  Copper-Mediated Synthesis of N-Acyl Vinylogous Carbamic Acids and Derivatives:  Synthesis of the Antibiotic CJ-15,801

  摘要：

  Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.

  DOI：

  10.1021/ol0360041

文献信息

• Development of a Novel Pd-Catalyzed <i>N</i>-Acyl Vinylogous Carbamate Synthesis for the Key Intermediate of ICE Inhibitor VX-765
  作者：Gerald J. Tanoury、Minzhang Chen、Yong Dong、Raymond E. Forslund、Derek Magdziak

  DOI：10.1021/ol702532h

  日期：2008.1.1

  A novel Pd-catalyzed coupling of Cbz-protected proline amide with 4-bromo-5-ethoxyfuran-2(5H)-one was developed for the synthesis of the P1-P2 unit (5) of VX-765. The process afforded quantitative coupling in the presence of water, providing a 1:1 mixture of 5 and its ethoxy epimer epi-5. Compound 5 was isolated as a single diastereomer via fractional crystallization, which was stereoselectively converted to 17 via hydrogenation, and subsequently transformed to VX-765. Nine examples of the Pd coupling are presented with yields ranging from 76-98%.
• Copper-Mediated Synthesis of <i>N</i>-Acyl Vinylogous Carbamic Acids and Derivatives:  Synthesis of the Antibiotic CJ-15,801
  作者：Chong Han、Ruichao Shen、Shun Su、John A. Porco

  DOI：10.1021/ol0360041

  日期：2004.1.1

  Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.