N-(2-乙氧基-5-氧代-2,5-二氢呋喃-3-基)丁酰胺 | 1005796-54-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: N-(2-乙氧基-5-氧代-2,5-二氢呋喃-3-基)丁酰胺
• 英文名称: N-(2-ethoxy-5-oxo-2,5-dihydrofuran-3-yl)butyramide
• 英文别名: N-(2-ethoxy-5-oxo-2H-furan-3-yl)butanamide
• CAS: 1005796-54-2
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: QTICDCYPUHMKQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丁酰胺 、 4-溴-5-乙氧基-2(5H)-呋喃酮 在 palladium diacetate 十六烷基三甲基溴化铵 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 、 水 为溶剂， 反应 1.0h， 以92%的产率得到N-(2-乙氧基-5-氧代-2,5-二氢呋喃-3-基)丁酰胺
  参考文献：
  名称：

  Development of a Novel Pd-Catalyzed N-Acyl Vinylogous Carbamate Synthesis for the Key Intermediate of ICE Inhibitor VX-765

  摘要：

  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%.

  DOI：

  10.1021/ol702532h

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%.