5-bromo-N-(2-methylbenzyl)furan-2-carboxamide | 1070313-41-5

• 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: 5-bromo-N-(2-methylbenzyl)furan-2-carboxamide
• 英文别名: 5-bromo-N-[(2-methylphenyl)methyl]furan-2-carboxamide
• CAS: 1070313-41-5
• 化学式: C₁₃H₁₂BrNO₂
• mdl: MFCD16240868
• 分子量: 294.148
• InChiKey: GMDTWLXEAYLNHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-N-(2-methylbenzyl)furan-2-carboxamide 、 3-苯并呋喃乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以20%的产率得到N-(2-(benzofuran-3-yl)acetyl)-5-bromo-N-(2-methylbenzyl)furan-2-carboxamide
  参考文献：
  名称：

  Cycloaddition Across the Benzofuran Ring as an Approach to the Morphine Alkaloids

  摘要：

  The intramolecular Diels-Alder reaction of several amidofurans tethered onto a benzofuran ring was examined as a strategy for the synthesis of morphine. Bromo substitution on the furan ring did not provide sufficient activation to allow the cycloaddition to take place across the aromatic benzofuran. However, the presence of a large o-methylbenzyl group on the amido nitrogen atom causes the reactive s-trans conformation of the amidofuran to be highly populated, thereby facilitating its Diels-Alder cycloaddition across a tethered benzofuran.

  DOI：

  10.1021/jo8016956
• 作为产物：
  描述：

  2-甲基苯甲基胺 、 5-溴呋喃-2-羰酰氯 在 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 5-bromo-N-(2-methylbenzyl)furan-2-carboxamide
  参考文献：
  名称：

  Cycloaddition Across the Benzofuran Ring as an Approach to the Morphine Alkaloids

  摘要：

  The intramolecular Diels-Alder reaction of several amidofurans tethered onto a benzofuran ring was examined as a strategy for the synthesis of morphine. Bromo substitution on the furan ring did not provide sufficient activation to allow the cycloaddition to take place across the aromatic benzofuran. However, the presence of a large o-methylbenzyl group on the amido nitrogen atom causes the reactive s-trans conformation of the amidofuran to be highly populated, thereby facilitating its Diels-Alder cycloaddition across a tethered benzofuran.

  DOI：

  10.1021/jo8016956

文献信息

• Cycloaddition Across the Benzofuran Ring as an Approach to the Morphine Alkaloids
  作者：Stefan France、Jutatip Boonsombat、Carolyn A. Leverett、Albert Padwa

  DOI：10.1021/jo8016956

  日期：2008.10.17

  The intramolecular Diels-Alder reaction of several amidofurans tethered onto a benzofuran ring was examined as a strategy for the synthesis of morphine. Bromo substitution on the furan ring did not provide sufficient activation to allow the cycloaddition to take place across the aromatic benzofuran. However, the presence of a large o-methylbenzyl group on the amido nitrogen atom causes the reactive s-trans conformation of the amidofuran to be highly populated, thereby facilitating its Diels-Alder cycloaddition across a tethered benzofuran.