外消旋-6-氟-3,4-二氢-4-氧代-2H-1-苯并吡喃-2-羧酸甲酯 | 134102-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 外消旋-6-氟-3,4-二氢-4-氧代-2H-1-苯并吡喃-2-羧酸甲酯
• 中文别名: rac-6-氟-3,4-二氢-4-氧代-2H-1-苯并吡喃-2-羧酸甲酯
• 英文名称: methyl 6-fluoro-4-oxo-3,4-dihydro-2H-chroman-2-carboxylate
• 英文别名: methyl 6-fluoro-4-oxochromane-2-carboxylate；rac-6-Fluoro-3,4-dihydro-4-oxo-2H-1-benzopyran-2-carboxylic Acid Methyl Ester；methyl 6-fluoro-4-oxo-2,3-dihydrochromene-2-carboxylate
• CAS: 134102-10-6
• 化学式: C₁₁H₉FO₄
• 分子量: 224.188
• InChiKey: WEEDYQYJCQNIPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  82 - 84°C
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、乙酸乙酯（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  5

反应信息

• 作为反应物：
  描述：

  外消旋-6-氟-3,4-二氢-4-氧代-2H-1-苯并吡喃-2-羧酸甲酯 在 盐酸 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 6-氟-3,4-二氢-2H-色烯-2-羧酸甲酯
  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：

  在 aluminum (III) chloride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 外消旋-6-氟-3,4-二氢-4-氧代-2H-1-苯并吡喃-2-羧酸甲酯
  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

• Reaction of methyl 3-[(dimethylamino)methylidene]-6-fluoro-4-oxo −3,4-dihydrochroman-2-carboxylate with primary and secondary amines*
  作者：A. I. Kysil、V. S. Moskvina、A. V. Turov、Z. V. Voitenko、V. P. Khilya

  DOI：10.1007/s10593-011-0859-0

  日期：2011.11

  A method was developed for substitution of the dimethylamino group by bioisosteric fragments by the action of various primary and secondary amines on methyl 3-[(dimethylamino)methylidene]-6-fluoro-4-oxo-3,4-dihydrochroman-2-carboxylate.

  开发了一种通过各种伯胺和仲胺对3-[（（二甲氨基）亚甲基] -6-氟-4-氧代-3,4-二氢苯并二氢-2-甲酸甲酯的作用而被生物等排片段取代的二甲基氨基的方法。
• Efficient synthesis of methyl 4-chloro-6-fluoro-3-formyl-2H-chromene-2-carboxylate and its derivatives
  作者：Andrii I. Kysil、Viktoria S. Moskvina、Marian V. Gorichko、Volodimyr P. Khilya

  DOI：10.1007/s00706-011-0595-2

  日期：2012.1

  Methyl 4-chloro-6-fluoro-3-formyl-2H-chromene-2-carboxylate was synthesized conveniently using Vilsmeier reagent. A series of new 2H-chromenes was prepared in high yields by introducing a corresponding beta-halovinylaldehyde into condensation and cyclization reactions with active methylene compounds.
• 10.1134/s1070363224030241
  作者：Li、Song、Yang、Yu、Tang、Wang

  DOI：10.1134/s1070363224030241

  日期：——
• 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.