2-(1,3-Dihydro-4-chloro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)acetaldehyde | 161036-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 2-(1,3-Dihydro-4-chloro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)acetaldehyde
• 英文别名: 2-(4-chloro-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)acetaldehyde
• CAS: 161036-69-7
• 化学式: C₁₂H₁₁ClO₄
• 分子量: 254.67
• InChiKey: IVXRMLLOMFQLIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1,3-Dihydro-4-chloro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)acetaldehyde 在 lithium hydroxide 、 magnesium 、 丙酸 作用下， 以 甲醇 为溶剂， 反应 6.5h， 生成 4-Chloromycophenolic acid
  参考文献：
  名称：

  The Alder-Rickert Reaction in a Synthesis of m-Chlorophenols and 4-Chloromycophenolic Acid

  摘要：

  A new synthesis of highly substituted m-chlorophenols 12 using the Alder-Rickert reaction between 1-chloro-3-(trimethylsiloxy)-1,3-cyclohexadienes 10 and activated acetylenes has been devised. This sequence has been shown to be highly regioselective when methyl propiolate is the dienophile, and the methodology has been adapted to a facile preparation of 4-chloromycophenolic acid (23).

  DOI：

  10.1021/jo00108a017
• 作为产物：
  描述：

  1-Chloro-4-methyl-2-(2-propenyl)-3-((trimethylsilyl)oxy)-1,3-cyclohexadiene 在 吡啶 、 lithium hydroxide 、 sodium tetrahydroborate 、 二甲基硫 、 乙酸酐 、 potassium carbonate 、 臭氧 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 18.5h， 生成 2-(1,3-Dihydro-4-chloro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)acetaldehyde
  参考文献：
  名称：

  The Alder-Rickert Reaction in a Synthesis of m-Chlorophenols and 4-Chloromycophenolic Acid

  摘要：

  A new synthesis of highly substituted m-chlorophenols 12 using the Alder-Rickert reaction between 1-chloro-3-(trimethylsiloxy)-1,3-cyclohexadienes 10 and activated acetylenes has been devised. This sequence has been shown to be highly regioselective when methyl propiolate is the dienophile, and the methodology has been adapted to a facile preparation of 4-chloromycophenolic acid (23).

  DOI：

  10.1021/jo00108a017

文献信息

• The Alder-Rickert Reaction in a Synthesis of m-Chlorophenols and 4-Chloromycophenolic Acid
  作者：John W. Patterson

  DOI：10.1021/jo00108a017

  日期：1995.2

  A new synthesis of highly substituted m-chlorophenols 12 using the Alder-Rickert reaction between 1-chloro-3-(trimethylsiloxy)-1,3-cyclohexadienes 10 and activated acetylenes has been devised. This sequence has been shown to be highly regioselective when methyl propiolate is the dienophile, and the methodology has been adapted to a facile preparation of 4-chloromycophenolic acid (23).