7-benzyloxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one | 869989-26-4

• 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: 7-benzyloxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one
• 英文别名: 2,6-Dimethyl-7-phenylmethoxychromeno[3,4-d][1,3]oxazol-4-one
• CAS: 869989-26-4
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: PBWMAPLZGQDSFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 以74%的产率得到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-3-nitrochromen-2-one 在 吡啶 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 7-benzyloxy-2,6-dimethylchromeno[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

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.