3-(2-furyl)-4-carboxy-1-isochromanone | 136918-46-2

• 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: 3-(2-furyl)-4-carboxy-1-isochromanone
• 英文别名: 3-(Furan-2-yl)-1-oxo-3,4-dihydroisochromene-4-carboxylic acid
• CAS: 136918-46-2；137667-80-2
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: BXPLFCDWYFFMHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-furyl)-4-carboxy-1-isochromanone 、 三甲基硅烷化重氮甲烷 在 甲醇 作用下， 以 乙醚 、 甲基叔丁基醚 为溶剂， 反应 0.5h， 以61.4 mg的产率得到(3R,4R)-methyl 3-(furan-2-yl)-1-oxoisochroman-4-carboxylate
  参考文献：
  名称：

  A Catalytic Asymmetric Reaction Involving Enolizable Anhydrides

  摘要：

  In the presence of a highly efficient novel bifunctional organocatalyst at low loadings under mild conditions, enolizable homophthalic anhydrides can be added to a range of aromatic and aliphatic aldehydes to give dihydroisocoumarins, with excellent yields and diastereo- and enantiocontrol (up to 99% ee).

  DOI：

  10.1021/ol300453s
• 作为产物：
  描述：

  邻羧基苯乙酸 在 3-[3,5-bis(trifluoromethyl)phenylamino]-4-[(S)-[6-methoxy-2-phenylquinolin-4-yl][(2S,4S,8R)-8-vinylquinuclidin-2-yl]methylamino]cyclobut-3-ene-1,2-dione 、 乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 甲基叔丁基醚 为溶剂， 反应 50.0h， 生成 trans-3-furan-2-yl-1-oxo-isochroman-4-carboxylic acid 、 3-(2-furyl)-4-carboxy-1-isochromanone
  参考文献：
  名称：

  A Catalytic Asymmetric Reaction Involving Enolizable Anhydrides

  摘要：

  In the presence of a highly efficient novel bifunctional organocatalyst at low loadings under mild conditions, enolizable homophthalic anhydrides can be added to a range of aromatic and aliphatic aldehydes to give dihydroisocoumarins, with excellent yields and diastereo- and enantiocontrol (up to 99% ee).

  DOI：

  10.1021/ol300453s

文献信息

• ENANTIOSELECTIVE ORGANIC ANHYDRIDE REACTIONS
  申请人：Connon Stephen J.

  公开号：US20130245268A1

  公开（公告）日：2013-09-19

  Disclosed herein is enantioselective synthetic method comprising reacting an enolisable C 4 -C 50 organic anhydride with a second compound selected from the group consisting of an aldehyde, a ketone, an aldimine, a ketimine or a Michael Acceptor in the presence of a bifunctional organocatalyst. The reaction may find particular utility in the enantioselective synthesis of medicinally relevant heterocycles, such as dihydroisocoumarins and dihydroisoquinolinones.

  本文披露了一种对映选择性合成方法，包括在双功能有机催化剂存在下，将可形成烯醇的C4-C50有机酐与来自醛、酮、醛亚胺、酮亚胺或迈克尔受体的第二化合物反应。该反应可能在对映选择性合成药用相关杂环化合物方面具有特殊的实用性，例如二氢异香豆素和二氢异喹啉酮。
• Enantioselective organic anhydride reactions
  申请人：The Provost, Fellows, Foundation Scholars, & the other members of Board, of the College of the Holy & Undiv. Trinity of Queen Elizabeth near Dublin

  公开号：EP2639212B1

  公开（公告）日：2016-03-09
• Kasatkin, A.N.; Biktimirov, R.Kh.; Tolstikov, G.A., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 4.1, p. 604 - 612
  作者：Kasatkin, A.N.、Biktimirov, R.Kh.、Tolstikov, G.A.、Sultanmuratowa, V.R.

  DOI：——

  日期：——
• US9050586B2
  申请人：——

  公开号：US9050586B2

  公开（公告）日：2015-06-09
• A Catalytic Asymmetric Reaction Involving Enolizable Anhydrides
  作者：Claudio Cornaggia、Francesco Manoni、Esther Torrente、Sean Tallon、Stephen J. Connon

  DOI：10.1021/ol300453s

  日期：2012.4.6

  In the presence of a highly efficient novel bifunctional organocatalyst at low loadings under mild conditions, enolizable homophthalic anhydrides can be added to a range of aromatic and aliphatic aldehydes to give dihydroisocoumarins, with excellent yields and diastereo- and enantiocontrol (up to 99% ee).