methyl (R)-6-bromo-4-oxochroman-2-carboxylate

• 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 (R)-6-bromo-4-oxochroman-2-carboxylate
• 英文别名: methyl (2R)-6-bromo-4-oxo-2,3-dihydrochromene-2-carboxylate
• 化学式: C₁₁H₉BrO₄
• 分子量: 285.094
• InChiKey: NCPXCLCRNYHBCX-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  methyl (R)-6-bromo-4-oxochroman-2-carboxylate 在 三乙基硅烷 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.0h， 生成 (R)-6-bromochroman-2-carboxylic acid
  参考文献：
  名称：

  An efficient and practical enantiospecific synthesis of methyl chromanone- and chroman-2-carboxylates

  摘要：

  Chromanone-2-carboxylates and chroman-2-carboxylates are useful building blocks for the synthesis of a variety of bioactive compounds, such as repinotan, fidarestat, and nebivolol. An efficient and practical enantiospecific synthesis of chromanone-2-carboxylates and chroman-2-carboxylates has been accomplished using intramolecular Mitsunobu etherification of methyl (S)-2-hydroxy-4-oxo-4-(2'-hydroxy)phenylbutanoates derived from L-malic acid. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.07.006
• 作为产物：
  描述：

  methyl (S)-4-(5-bromo-2-hydroxyphenyl)-2-hydroxy-4-oxo-butanoate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以55%的产率得到methyl (R)-6-bromo-4-oxochroman-2-carboxylate
  参考文献：
  名称：

  An efficient and practical enantiospecific synthesis of methyl chromanone- and chroman-2-carboxylates

  摘要：

  Chromanone-2-carboxylates and chroman-2-carboxylates are useful building blocks for the synthesis of a variety of bioactive compounds, such as repinotan, fidarestat, and nebivolol. An efficient and practical enantiospecific synthesis of chromanone-2-carboxylates and chroman-2-carboxylates has been accomplished using intramolecular Mitsunobu etherification of methyl (S)-2-hydroxy-4-oxo-4-(2'-hydroxy)phenylbutanoates derived from L-malic acid. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.07.006

文献信息

• An efficient and practical enantiospecific synthesis of methyl chromanone- and chroman-2-carboxylates
  作者：Dong Woon Kim、Md. Maqusood Alam、Young Hun Lee、M. Naseer A. Khan、Yong Zhang、Yong Sup Lee

  DOI：10.1016/j.tetasy.2015.07.006

  日期：2015.9

  Chromanone-2-carboxylates and chroman-2-carboxylates are useful building blocks for the synthesis of a variety of bioactive compounds, such as repinotan, fidarestat, and nebivolol. An efficient and practical enantiospecific synthesis of chromanone-2-carboxylates and chroman-2-carboxylates has been accomplished using intramolecular Mitsunobu etherification of methyl (S)-2-hydroxy-4-oxo-4-(2'-hydroxy)phenylbutanoates derived from L-malic acid. (C) 2015 Elsevier Ltd. All rights reserved.