diethyl isobenzofuran-1,1(3H)dicarboxylate | 1400892-35-4

• 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: diethyl isobenzofuran-1,1(3H)dicarboxylate
• 英文别名: diethyl 3H-2-benzofuran-1,1-dicarboxylate
• CAS: 1400892-35-4
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: GACHJOUNFKMTLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl isobenzofuran-1,1(3H)dicarboxylate 在 lithium tri-t-butoxyaluminum hydride 、 potassium hydrogensulfate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以42%的产率得到ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate
  参考文献：
  名称：

  1,4-Addition of an aryllithium reagent to diethyl ketomalonate. Scalable synthesis of ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate

  摘要：

  While optimizing the synthesis of pharmaceutical building block 3 [ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate], we encountered an unusual addition of an aryllithium reagent to the ketone oxygen atom of diethyl ketomalonate. Compound 3 was ultimately prepared on a large scale by a two-step sequence involving (1) annulation of a functionalized Grignard reagent with diethyl ketomalonate and (2) selective mono-reduction of a geminal diester using lithium tri-tert-butoxyaluminum hydride. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.052
• 作为产物：
  描述：

  甲撑丙二酸二乙酯 、 邻碘氯苄 在 异丙基氯化镁 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以62%的产率得到diethyl isobenzofuran-1,1(3H)dicarboxylate
  参考文献：
  名称：

  1,4-Addition of an aryllithium reagent to diethyl ketomalonate. Scalable synthesis of ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate

  摘要：

  While optimizing the synthesis of pharmaceutical building block 3 [ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate], we encountered an unusual addition of an aryllithium reagent to the ketone oxygen atom of diethyl ketomalonate. Compound 3 was ultimately prepared on a large scale by a two-step sequence involving (1) annulation of a functionalized Grignard reagent with diethyl ketomalonate and (2) selective mono-reduction of a geminal diester using lithium tri-tert-butoxyaluminum hydride. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.052