[3-(methoxymethoxy)naphthalen-2-yl]-[(2R,3R)-3-methyloxiran-2-yl]methanone | 226565-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [3-(methoxymethoxy)naphthalen-2-yl]-[(2R,3R)-3-methyloxiran-2-yl]methanone
• CAS: 226565-96-4
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: WLWVFWPBDIBMGP-QLJPJBMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  [3-(methoxymethoxy)naphthalen-2-yl]-[(2R,3R)-3-methyloxiran-2-yl]methanone 在 高氯酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以44%的产率得到(2S,3R)-3-hydroxy-2-methyl-2,3-dihydrobenzo[g]chromen-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：

  2-(methoxymethoxy)naphthalene 、 (2R,3R)-N-甲氧基-N,3-二甲基-2-环氧乙烷甲酰胺 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 2.0h， 以47%的产率得到[3-(methoxymethoxy)naphthalen-2-yl]-[(2R,3R)-3-methyloxiran-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.