[2-(methoxymethoxy)phenyl]-[(2R,3S)-3-propyloxiran-2-yl]methanone | 226565-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(methoxymethoxy)phenyl]-[(2R,3S)-3-propyloxiran-2-yl]methanone
• CAS: 226565-78-2
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: ZRAGDQWFMYAABU-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-(methoxymethoxy)phenyl]-[(2R,3S)-3-propyloxiran-2-yl]methanone 在 高氯酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以89%的产率得到(2R,3R)-3-hydroxy-2-propyl-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  Ring Transformation of Glycidic Amides with Ortho-Metalated Phenols to Enantiopure 3-Hydroxychromanones

  摘要：

  A novel access to hitherto unknown enantiopure 2-alkylchroman-4-ones 10 was found by a reaction of ortho-metalated O-MOM-protected phenols with Weinreb amides 8 of enantiopure cis- or trans-glycidic acids, Upon acidic hydrolysis, the resulting o-MOMO-benzoyloxiranes 9 undergo ring transformation to 2-alkylchroman-4-ones 10. 2-Alkylidenecoumaran-3-ones 11 were formed as alternative products, depending on the configuration of the starting oxirane ring and on the type of phenol used as starting material.

  DOI：

  10.1021/jo982242b
• 作为产物：
  描述：

  trans-α,β-epoxyhexanoic acid 在 叔丁基锂 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 22.0h， 生成 [2-(methoxymethoxy)phenyl]-[(2R,3S)-3-propyloxiran-2-yl]methanone
  参考文献：
  名称：

  Ring Transformation of Glycidic Amides with Ortho-Metalated Phenols to Enantiopure 3-Hydroxychromanones

  摘要：

  A novel access to hitherto unknown enantiopure 2-alkylchroman-4-ones 10 was found by a reaction of ortho-metalated O-MOM-protected phenols with Weinreb amides 8 of enantiopure cis- or trans-glycidic acids, Upon acidic hydrolysis, the resulting o-MOMO-benzoyloxiranes 9 undergo ring transformation to 2-alkylchroman-4-ones 10. 2-Alkylidenecoumaran-3-ones 11 were formed as alternative products, depending on the configuration of the starting oxirane ring and on the type of phenol used as starting material.

  DOI：

  10.1021/jo982242b

文献信息

• Ring Transformation of Glycidic Amides with <i>Ortho</i>-Metalated Phenols to Enantiopure 3-Hydroxychromanones
  作者：Karsten Woydowski、Burkhard Ziemer、Jürgen Liebscher

  DOI：10.1021/jo982242b

  日期：1999.5.1

  A novel access to hitherto unknown enantiopure 2-alkylchroman-4-ones 10 was found by a reaction of ortho-metalated O-MOM-protected phenols with Weinreb amides 8 of enantiopure cis- or trans-glycidic acids, Upon acidic hydrolysis, the resulting o-MOMO-benzoyloxiranes 9 undergo ring transformation to 2-alkylchroman-4-ones 10. 2-Alkylidenecoumaran-3-ones 11 were formed as alternative products, depending on the configuration of the starting oxirane ring and on the type of phenol used as starting material.