methyl (S)-2-(4,6-dihydroxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetate | 1252651-98-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (S)-2-(4,6-dihydroxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetate
• 英文别名: methyl 2-[(1S)-4,6-dihydroxy-3-oxo-1H-2-benzofuran-1-yl]acetate
• CAS: 1252651-98-1
• 化学式: C₁₁H₁₀O₆
• 分子量: 238.197
• InChiKey: MYZZMOFGVNKLDN-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-(4,6-dihydroxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetate 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (S)-2-(4,6-dihydroxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetic acid
  参考文献：
  名称：

  Heteroatom-Directed Reverse Wacker Oxidations. Synthesis of the Reported Structure of (−)-Herbaric Acid

  摘要：

  A microwave-assisted chemoenzymatic resolution has been used to install the C3 stercocenter of the reported structure of the fungal metabolite herbaric acid in high enantiomeric excess. The synthesis and stereochemical assignment was accomplished using a completely regioselective anti-Mark ovnikov addition of water to vinylphthalide 3, achieved using a heteroatom-directed Wacker oxidation that proceeds with retention of stereochemistry. These results establish that so-called "reverse" Wacker oxidations are a viable alternative to hydroboration/oxidation procedures.

  DOI：

  10.1021/jo1016585
• 作为产物：
  描述：

  (S)-3-(ethoxycarbonyl)methyl-5,7-dimethoxyphthalide 在 三溴化硼 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 74.0h， 生成 methyl (S)-2-(4,6-dihydroxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetate 、 (S)-2-(4,6-dihydroxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetic acid
  参考文献：
  名称：

  Heteroatom-Directed Reverse Wacker Oxidations. Synthesis of the Reported Structure of (−)-Herbaric Acid

  摘要：

  A microwave-assisted chemoenzymatic resolution has been used to install the C3 stercocenter of the reported structure of the fungal metabolite herbaric acid in high enantiomeric excess. The synthesis and stereochemical assignment was accomplished using a completely regioselective anti-Mark ovnikov addition of water to vinylphthalide 3, achieved using a heteroatom-directed Wacker oxidation that proceeds with retention of stereochemistry. These results establish that so-called "reverse" Wacker oxidations are a viable alternative to hydroboration/oxidation procedures.

  DOI：

  10.1021/jo1016585

文献信息

• Heteroatom-Directed Reverse Wacker Oxidations. Synthesis of the Reported Structure of (−)-Herbaric Acid
  作者：Peter J. Choi、Jonathan Sperry、Margaret A. Brimble

  DOI：10.1021/jo1016585

  日期：2010.11.5

  A microwave-assisted chemoenzymatic resolution has been used to install the C3 stercocenter of the reported structure of the fungal metabolite herbaric acid in high enantiomeric excess. The synthesis and stereochemical assignment was accomplished using a completely regioselective anti-Mark ovnikov addition of water to vinylphthalide 3, achieved using a heteroatom-directed Wacker oxidation that proceeds with retention of stereochemistry. These results establish that so-called "reverse" Wacker oxidations are a viable alternative to hydroboration/oxidation procedures.