trans-6-oxo-11-thiophen-2-yl-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic aicd methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: trans-6-oxo-11-thiophen-2-yl-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic aicd methyl ester
• 英文别名: methyl (11R,12R)-6-oxo-11-thiophen-2-yl-11,12-dihydronaphtho[1,2-c]isochromene-12-carboxylate
• 化学式: C₂₃H₁₆O₄S
• 分子量: 388.444
• InChiKey: NFJWTCROXQOWBU-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 2-噻吩甲醛 、 高邻苯二甲酸酐 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 7.0h， 以34%的产率得到(3R,4R)-methyl 1-oxo-3-(thiophen-2-y)isochroman-4-carboxylate
  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

• 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.