3-ethoxy-3-methyl-1,3-dihydro-2-benzofuran-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-ethoxy-3-methyl-1,3-dihydro-2-benzofuran-1-one
• 英文别名: 3-ethoxy-3-methyl-3H-isobenzofuran-1-one；3-ethoxy-3-methylphthalide；3-Ethoxy-methylphthalide；3-ethoxy-3-methyl-2-benzofuran-1-one
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: PGXCYAHIERNBMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙二酸二乙酯 、 3-ethoxy-3-methyl-1,3-dihydro-2-benzofuran-1-one 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以89%的产率得到2-(1-methyl-3-oxo-1,3-dihydro-isobenzofuran-1-yl)malonic acid diethyl ester
  参考文献：
  名称：

  A Facile Synthesis of 3‐Substituted Phthalides

  摘要：

  1(3H)-Isobenzofuranone (phthalides) and its derivatives possess a wide range of biological activities. A new method was found for the synthesis of 3-substituted phthalides featured with the convenient condensation reaction of 3-ethoxyphthalide with carbanions in high yields.

  DOI：

  10.1081/scc-120030304
• 作为产物：
  描述：

  2-乙酰苯甲酸 、 乙醇 在 硫酸 作用下， 以 苯 为溶剂， 反应 4.0h， 以47%的产率得到3-ethoxy-3-methyl-1,3-dihydro-2-benzofuran-1-one
  参考文献：
  名称：

  A Facile Synthesis of 3‐Substituted Phthalides

  摘要：

  1(3H)-Isobenzofuranone (phthalides) and its derivatives possess a wide range of biological activities. A new method was found for the synthesis of 3-substituted phthalides featured with the convenient condensation reaction of 3-ethoxyphthalide with carbanions in high yields.

  DOI：

  10.1081/scc-120030304

文献信息

• Oxidative cyclization of dialdehydes with alcohols and 1,3-dicarbonyl compounds under Rh(III)/Cu(II) conditions
  作者：Takanori Matsuda、Kentaro Suzuki、Shinya Abe、Haruki Kirikae、Noboru Okada

  DOI：10.1016/j.tet.2015.10.034

  日期：2015.12

  For the preparation of 3-alkoxyphthalides from phthalaldehydes and alcohols, a cyclization reaction in the presence of a rhodium(III) catalyst and copper(II) salt is reported. Cyclization of phthalaldehydes also occurs with 1,3-dicarbonyl compounds under similar conditions to produce 3-substituted phthalides in good yields. An acylrhodium(III) species might be a key intermediate in these cyclization

  对于从phthalaldehydes和醇3- alkoxyphthalides制备，则报告在铑（III）催化剂和铜的存在下进行环化反应（II）盐。phthalaldehydes的环化也会发生与在类似条件下的1,3-二羰基化合物，以良好的产率生产3-取代的苯酞。酰基铑（III）可能是这些环化反应中的关键中间体。
• A Facile Synthesis of 3‐Substituted Phthalides
  作者：Guo Li、Dali Yin、Xiao‐Tian Liang

  DOI：10.1081/scc-120030304

  日期：2004.12.31

  1(3H)-Isobenzofuranone (phthalides) and its derivatives possess a wide range of biological activities. A new method was found for the synthesis of 3-substituted phthalides featured with the convenient condensation reaction of 3-ethoxyphthalide with carbanions in high yields.