ethyl 4-oxo-4H-benzo[h]chromene-2-carboxylate | 92965-13-4

• 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: ethyl 4-oxo-4H-benzo[h]chromene-2-carboxylate
• 英文别名: ethyl 4-oxo-4H-benzo[h]chromene-2-carboxyate；2-carbethoxy-4-oxonaphtho[1,2-b]pyran；4-oxo-4H-benzo[h]chromene-2-carboxylic acid ethyl ester；4-Oxo-4H-benzo[h]chromen-2-carbonsaeure-aethylester；Ethyl 4-oxobenzo[h]chromene-2-carboxylate
• CAS: 92965-13-4
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: CQDQWQZUWVOKFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-oxo-4H-benzo[h]chromene-2-carboxylate 在 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 异丙醇 为溶剂， 反应 18.0h， 生成 (3,4-dihydro-2H-benzo[h]chromen-2-yl)methanol
  参考文献：
  名称：

  Design and synthesis of 3,4-dihydro-2H-benzo[h]chromene derivatives as potential NF-κB inhibitors

  摘要：

  A novel class of NF-kappa B inhibitors were designed and synthesized based on KL-1156 (6-hydroxy-7-methoxychroman-2-carboxylic acid phenyl amide) which is unambiguously considered to be a promising inhibitor for the translocation step of NF-kappa B. Especially in this study we focused on the modifying the chroman moiety of KL-1156 into four parts for exploring the SAR studies linked with physical properties of substituents resulted the development of novel 1a-k, 2a-f, 3a-d and 4a-d derivatives of 3,4-dihydro-2H-benzo[h] chromene. From the SAR studies we were very delightfully identified that several new N-aryl-3,4-dihydro-2H-benzo[h] chromene-2-carboxamide derivatives (1a-k) exhibited good inhibitory activity and anti-proliferative activity than parent lead compound KL-1156, among them 1i exhibited outstanding inhibitory effect on LPS-induced NF-kappa B transcriptional activity and anti-proliferative activity on NCI-H23 lung cancer cell lines than KL-1156. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.053
• 作为产物：
  描述：

  ethyl 2-hydroxy-4-oxo-3H-benzo[h]chromene-2-carboxylate 生成 ethyl 4-oxo-4H-benzo[h]chromene-2-carboxylate
  参考文献：
  名称：

  MARKEES, DIETHER G., J. HETEROCYCL. CHEM., 26,(1989) N, C. 29-32

  摘要：

  DOI：

文献信息

• Synthesis of Amide and Ester Derivatives of Naphthopyrone Carboxylic Acid
  作者：J. N. Soni、S. S. Soman

  DOI：10.1002/jhet.2136

  日期：2014.7

  The synthesis of various amide and ester derivatives of naphthopyrone‐2‐carboxylic acid has been carried out by reaction of 1‐naphthol with dimethyl acetylenedicarboxylate, which gave a mixture of E and Z isomers of naphthoxy diester. The diester on hydrolysis with KOH gave corresponding diacid, which was a mixture of E and Z isomers. The E and Z isomers were difficult to separate, which were subjected

  萘并吡喃酮-2-羧酸的各种酰胺和酯衍生物的合成是通过1-萘酚与乙炔二羧酸二甲酯的反应进行的，从而得到萘氧基二酯的E和Z异构体的混合物。用KOH水解的二酯得到相应的二酸，其为E和Z异构体的混合物。的Ë和ž异构体难以分离，将其进行环化在硫酸以获得环化的naphthopyrone羧酸。该酸被转化为标题化合物。
• Bondarev, Mikhail; Iwamura, Tatsunori; Hynd, Donna, Medicinal Chemistry Research, 1998, vol. 8, # 6, p. 333 - 342
  作者：Bondarev, Mikhail、Iwamura, Tatsunori、Hynd, Donna、Mazzocco, Lucia、Lee, David K. H.、Dukat, Malgorzata、Glennon, Richard A.

  DOI：——

  日期：——
• Markees, Diether G., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 29 - 32
  作者：Markees, Diether G.

  DOI：——

  日期：——
• Pfeiffer; Grimmer, Chemische Berichte, 1917, vol. 50, p. 917
  作者：Pfeiffer、Grimmer

  DOI：——

  日期：——
• MARKEES, DIETHER G., J. HETEROCYCL. CHEM., 26,(1989) N, C. 29-32
  作者：MARKEES, DIETHER G.

  DOI：——

  日期：——