(3S,4R)-1-oxo-3-thiophen-2-yl-3,4-dihydroisochromene-4-carboxylic acid

• 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: (3S,4R)-1-oxo-3-thiophen-2-yl-3,4-dihydroisochromene-4-carboxylic acid
• 化学式: C₁₄H₁₀O₄S
• 分子量: 274.297
• InChiKey: WPKSUTPJUIBQJU-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 高邻苯二甲酸酐 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以75%的产率得到trans-3-thiophen-2-yl-1-oxo-isochroman-4-carboxylic acid
  参考文献：
  名称：

  cis/trans-Isochromanones. DMAP induced cycloaddition of homophthalic anhydride and aldehydes

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.01.040

文献信息

• Catalytic Asymmetric Cycloadditions between Aldehydes and Enolizable Anhydrides: <i>cis</i>-Selective Dihydroisocoumarin Formation
  作者：Maria Luisa Aiello、Umar Farid、Cristina Trujillo、Brendan Twamley、Stephen J. Connon

  DOI：10.1021/acs.joc.8b02332

  日期：2018.12.21

  In the presence of a trityl-substituted cinchona alkaloid-based catalyst, homophthalic, aryl succinic, and glutaconic anhydride derivatives reacted with aromatic and aliphatic aldehydes to produce cis-lactones in up to 90:10 dr and 99% ee. A DFT study has shown how the catalyst is uniquely able to bring about the opposite sense of diastereocontrol to that usually observed.

  在三苯甲基取代的金鸡纳生物碱基催化剂的存在下，高邻苯二甲酸，芳基琥珀酸和戊二酸酐衍生物与芳族和脂族醛反应生成顺式内酯，其最高90:10 dr和99％ee。DFT研究表明，催化剂如何独特地带来与通常观察到的相反的非对映控制感。
• 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.