Ethyl 1-[[(3-methoxy-5-isoxazolyl)carbonyl]amino]cyclopropanecarboxylate | 1160936-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 1-[[(3-methoxy-5-isoxazolyl)carbonyl]amino]cyclopropanecarboxylate
• 英文别名: ethyl 1-[(3-methoxy-1,2-oxazole-5-carbonyl)amino]cyclopropane-1-carboxylate
• CAS: 1160936-56-0
• 化学式: C₁₁H₁₄N₂O₅
• 分子量: 254.243
• InChiKey: QRQMWBGSOOWUMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 1-[[(3-methoxy-5-isoxazolyl)carbonyl]amino]cyclopropanecarboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以84%的产率得到1-[(3-methoxy-isoxazole-5-carbonyl)-amino]-cyclopropanecarboxylic acid
  参考文献：
  名称：

  Practical Synthesis of a Potent Bradykinin B₁ Antagonist via Enantioselective Hydrogenation of a Pyridyl N-Acyl Enamide

  摘要：

  A practical and efficient synthesis of bradykinin B I antagonist I is described. A convergent strategy was utilized which involved synthesis of three fragments: 3, 6, and 7. Cross coupling of fragments 6 and 7 followed by amidation with 3 enabled efficient synthesis of I in 19 steps total, a 35% overall yield from commercially available pyridine 10. The key to the success of the synthesis was the development of a fluorodenitration step to install the fluorine in pyridine 7 and a catalytic enantioselective hydrogenation of N-acyl enamide 9 to set the stereochemistry.

  DOI：

  10.1021/jo802772d
• 作为产物：
  描述：

  氨基酸盐酸盐 、 3-甲氧基-1,2-恶唑-5-甲酰氯 在 potassium carbonate 作用下， 以 甲基叔丁基醚 、 水 为溶剂， 生成 Ethyl 1-[[(3-methoxy-5-isoxazolyl)carbonyl]amino]cyclopropanecarboxylate
  参考文献：
  名称：

  Practical Synthesis of a Potent Bradykinin B₁ Antagonist via Enantioselective Hydrogenation of a Pyridyl N-Acyl Enamide

  摘要：

  A practical and efficient synthesis of bradykinin B I antagonist I is described. A convergent strategy was utilized which involved synthesis of three fragments: 3, 6, and 7. Cross coupling of fragments 6 and 7 followed by amidation with 3 enabled efficient synthesis of I in 19 steps total, a 35% overall yield from commercially available pyridine 10. The key to the success of the synthesis was the development of a fluorodenitration step to install the fluorine in pyridine 7 and a catalytic enantioselective hydrogenation of N-acyl enamide 9 to set the stereochemistry.

  DOI：

  10.1021/jo802772d

文献信息

• Practical Synthesis of a Potent Bradykinin B₁ Antagonist via Enantioselective Hydrogenation of a Pyridyl <i>N</i>-Acyl Enamide
  作者：Paul D. O’Shea、Danny Gauvreau、Francis Gosselin、Greg Hughes、Christian Nadeau、Amélie Roy、C. Scott Shultz

  DOI：10.1021/jo802772d

  日期：2009.6.19

  A practical and efficient synthesis of bradykinin B I antagonist I is described. A convergent strategy was utilized which involved synthesis of three fragments: 3, 6, and 7. Cross coupling of fragments 6 and 7 followed by amidation with 3 enabled efficient synthesis of I in 19 steps total, a 35% overall yield from commercially available pyridine 10. The key to the success of the synthesis was the development of a fluorodenitration step to install the fluorine in pyridine 7 and a catalytic enantioselective hydrogenation of N-acyl enamide 9 to set the stereochemistry.