N-(7-benzyloxy-4-hydroxy-8-methyl-2-oxo-(2H)-chromen-3-yl)-acetamide | 869989-24-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(7-benzyloxy-4-hydroxy-8-methyl-2-oxo-(2H)-chromen-3-yl)-acetamide
• 英文别名: N-(4-hydroxy-8-methyl-2-oxo-7-phenylmethoxychromen-3-yl)acetamide
• CAS: 869989-24-2
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: FDFWPPMBYPCYHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(7-benzyloxy-4-hydroxy-8-methyl-2-oxo-(2H)-chromen-3-yl)-acetamide 在 palladium on activated charcoal 吡啶 、 氢气 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 2,6-dimethyl-7-hydroxychromeno[3,4-d]oxazol-4-one
  参考文献：
  名称：

  An efficient synthesis of 7-hydroxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one—a protected fragment of novenamine

  摘要：

  The high-yielding six-step synthesis of 7-hydroxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one 17 from commercially available 2,4-dihydroxy-3-methylacetophenone is described. Coumarin 17 constitutes a useful synthon for cournarin antibiotic synthesis. A new methodology for oxazole formation applicable to 3-aminocournarins has been developed, and a mechanistic rationalization is proposed. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.08.083
• 作为产物：
  描述：

  7-(benzyloxy)-4-hydroxy-8-methyl-2H-chromen-2-one 在 硫酸 、 硝酸 、 锌 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 N-(7-benzyloxy-4-hydroxy-8-methyl-2-oxo-(2H)-chromen-3-yl)-acetamide
  参考文献：
  名称：

  An efficient synthesis of 7-hydroxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one—a protected fragment of novenamine

  摘要：

  The high-yielding six-step synthesis of 7-hydroxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one 17 from commercially available 2,4-dihydroxy-3-methylacetophenone is described. Coumarin 17 constitutes a useful synthon for cournarin antibiotic synthesis. A new methodology for oxazole formation applicable to 3-aminocournarins has been developed, and a mechanistic rationalization is proposed. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.08.083

文献信息

• An efficient synthesis of 7-hydroxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one—a protected fragment of novenamine
  作者：David W. Gammon、Roger Hunter、Seanette A. Wilson

  DOI：10.1016/j.tet.2005.08.083

  日期：2005.11

  The high-yielding six-step synthesis of 7-hydroxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one 17 from commercially available 2,4-dihydroxy-3-methylacetophenone is described. Coumarin 17 constitutes a useful synthon for cournarin antibiotic synthesis. A new methodology for oxazole formation applicable to 3-aminocournarins has been developed, and a mechanistic rationalization is proposed. (c) 2005 Published by Elsevier Ltd.