methyl 6-hydroxy-5-methoxy-2H-chromene-2-carboxylate | 1352196-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 6-hydroxy-5-methoxy-2H-chromene-2-carboxylate
• CAS: 1352196-74-7
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: MMMZBBYQMVZLDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  以 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 36.0h， 以58%的产率得到methyl 6-hydroxy-5-methoxy-2H-chromene-2-carboxylate
  参考文献：
  名称：

  Convergent synthesis of 2H-chromenes—a formal [3+3] cycloaddition by a one-pot, three-step cascade

  摘要：

  In cases in which the palladium-catalyzed coupling of a bromoquinone with a vinyl stannane affords a vinyl quinone that enolizes, the resulting ortho-quinone methide undergoes an oxa-6 pi electrocyclization. Enolization is promoted by the presence of a polar additive. The net conversion is a formal [3+3] cycloaddition that gives 2H-chromenes. Because the first two steps of the cascade are catalyzed, the overall conversion is an example of multicatalysis. Yields for the optimized, one-pot protocol are dramatically improved over the conventional stepwise process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.068

文献信息

• Convergent synthesis of 2H-chromenes—a formal [3+3] cycloaddition by a one-pot, three-step cascade
  作者：Kathlyn A. Parker、Thomas L. Mindt

  DOI：10.1016/j.tet.2011.09.068

  日期：2011.12

  In cases in which the palladium-catalyzed coupling of a bromoquinone with a vinyl stannane affords a vinyl quinone that enolizes, the resulting ortho-quinone methide undergoes an oxa-6 pi electrocyclization. Enolization is promoted by the presence of a polar additive. The net conversion is a formal [3+3] cycloaddition that gives 2H-chromenes. Because the first two steps of the cascade are catalyzed, the overall conversion is an example of multicatalysis. Yields for the optimized, one-pot protocol are dramatically improved over the conventional stepwise process. (C) 2011 Elsevier Ltd. All rights reserved.