trans-3-furan-2-yl-1-oxo-isochroman-4-carboxylic acid | 1370021-94-5

• 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: trans-3-furan-2-yl-1-oxo-isochroman-4-carboxylic acid
• CAS: 1370021-94-5
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: BXPLFCDWYFFMHX-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.74
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 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
  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

• cis/trans-Isochromanones. DMAP induced cycloaddition of homophthalic anhydride and aldehydes
  作者：Milen G Bogdanov、Mariana D Palamareva

  DOI：10.1016/j.tet.2004.01.040

  日期：2004.3

  Homophthalic anhydride (1) reacts with wide variety of aromatic aldehydes, in the presence of chloroform and DMAP (N,N-dimethyl-4-amino-pyridine) at room temperature, to give in high yields cis- and trans-1-oxo-isochroman-4-carboxylic acids. Under these conditions, the trans-isomer is predominant and formation of Perkin-type products was not observed in contrast to the reaction carried out in the presence of pyridine. The unexpected trans-6-oxo-11-thiophen-2-yl-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic acid methyl ester (8) was isolated when the reaction between 1 and thiophene-2-carbaldehyde was carried out in pyridine. (C) 2004 Elsevier Ltd. All rights reserved.