4,4-dimethyl-2-(6-hydroxy-2-methoxy-4,5-(methylenedioxy)phenyl)-2-oxazoline | 173424-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4,4-dimethyl-2-(6-hydroxy-2-methoxy-4,5-(methylenedioxy)phenyl)-2-oxazoline
• 英文别名: 5-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-6-methoxy-1,3-benzodioxol-4-ol
• CAS: 173424-91-4
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: JIILTONWRAIUIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-2-(6-hydroxy-2-methoxy-4,5-(methylenedioxy)phenyl)-2-oxazoline 在 氢氧化钾 、 1,1,2,2-四氟-1,2-二溴乙烷 、 magnesium 作用下， 以 二甲基亚砜 为溶剂， 反应 13.0h， 生成 2-[4-(1-benzyl-2,3-dihydroindol-7-yl)-6-methoxy-1,3-benzodioxol-5-yl]-4,4-dimethyl-5H-1,3-oxazole
  参考文献：
  名称：

  An Oxazoline-Mediated Synthesis of the Pyrrolophenanthridine Alkaloids and Some Novel Derivatives

  摘要：

  An unsymmetrical biaryl coupling between the Grignard of N-benzyl-7-bromoindoline 25 and the appropriately substituted (o-methoxyaryl)oxazoline 15 leads to an intermediate biaryl which can be elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system. This simple two-step sequence provides general access to the pyrrolophenanthridine alkaloids 2-6.

  DOI：

  10.1021/jo951474x
• 作为产物：
  描述：

  6-溴苯并[d][1,3]二氧代-5-羧酸 在 盐酸 、 正丁基锂 、 磺酰氯 、 草酰氯 、 双(三甲基硅基)过氧化物 、 sodium methylate 、 铜 作用下， 反应 19.0h， 生成 4,4-dimethyl-2-(6-hydroxy-2-methoxy-4,5-(methylenedioxy)phenyl)-2-oxazoline
  参考文献：
  名称：

  An Oxazoline-Mediated Synthesis of the Pyrrolophenanthridine Alkaloids and Some Novel Derivatives

  摘要：

  An unsymmetrical biaryl coupling between the Grignard of N-benzyl-7-bromoindoline 25 and the appropriately substituted (o-methoxyaryl)oxazoline 15 leads to an intermediate biaryl which can be elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system. This simple two-step sequence provides general access to the pyrrolophenanthridine alkaloids 2-6.

  DOI：

  10.1021/jo951474x

文献信息

• An Oxazoline-Mediated Synthesis of the Pyrrolophenanthridine Alkaloids and Some Novel Derivatives
  作者：Richard H. Hutchings、A. I. Meyers

  DOI：10.1021/jo951474x

  日期：1996.1.1

  An unsymmetrical biaryl coupling between the Grignard of N-benzyl-7-bromoindoline 25 and the appropriately substituted (o-methoxyaryl)oxazoline 15 leads to an intermediate biaryl which can be elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system. This simple two-step sequence provides general access to the pyrrolophenanthridine alkaloids 2-6.