diethyl 6-(tert-butoxy)-3-hydroxybenzofuran-2,2(3H)dicarboxylate | 1400892-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: diethyl 6-(tert-butoxy)-3-hydroxybenzofuran-2,2(3H)dicarboxylate
• 英文别名: diethyl 3-hydroxy-6-[(2-methylpropan-2-yl)oxy]-3H-1-benzofuran-2,2-dicarboxylate
• CAS: 1400892-33-2
• 化学式: C₁₈H₂₄O₇
• 分子量: 352.384
• InChiKey: DLGPTQVKVWTIEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲撑丙二酸二乙酯 、 对叔丁氧基苯甲醛 在 正丁基锂 、 N,N,N'-三甲基乙二胺 、 盐酸 、 水 作用下， 以 2-甲基四氢呋喃 、 正己烷 为溶剂， 反应 24.22h， 生成 diethyl 6-(tert-butoxy)-3-hydroxybenzofuran-2,2(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

文献信息

• 1,4-Addition of an aryllithium reagent to diethyl ketomalonate. Scalable synthesis of ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate
  作者：Benjamin N. Rocke、Edward L. Conn、Shane A. Eisenbeis、Roger B. Ruggeri

  DOI：10.1016/j.tetlet.2012.05.052

  日期：2012.10

  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.