4-cyano-7-methoxy-2H-1-benzopyran-2-one | 84097-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-cyano-7-methoxy-2H-1-benzopyran-2-one
• 英文别名: 4-Cyano-7-methoxycoumarin；7-Methoxy-2-oxochromene-4-carbonitrile
• CAS: 84097-06-3
• 化学式: C₁₁H₇NO₃
• 分子量: 201.181
• InChiKey: XGMVGDYQDKQLCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-cyano-7-methoxy-2H-1-benzopyran-2-one 在 硫酸 作用下， 反应 12.0h， 生成 7-methoxycoumarin-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and rat lens aldose reductase inhibitory activity of some benzopyran-2-ones

  摘要：

  A number of 4,7-disubstituted benzopyran-2-ones were synthesized and evaluated for crude rat lens aldose reductase inhibitory activity. Substituents on position 4 included CH3, CO2H, CH2CO2H, CH = CHCO2H, and CH2CH2CO2H. The aromatic substituents included OH, OCH3, OCOCH3, CH2CH3, and Cl. Also included in the study were 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic, 2-oxo-2H-naphtho[1,2-b]pyran-4-acetic, and 1-naphthylacetic acids. The benzopyran and naphthopyran derivatives were prepared by the classical von Pechmann reaction. General structure-activity relationships reveal that optimal enzyme inhibitory activity is displayed by those compounds possessing the acetic acid moiety. For example, the most potent derivative, 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic acid with an IC50 of 0.020 microM, is as potent as sorbinil (IC50 = 0.017 microM) in the crude rat lens aldose reductase assay.

  DOI：

  10.1021/jm00156a031
• 作为产物：
  描述：

  7-甲氧基-4-甲基香豆素 在 selenium(IV) oxide 、 盐酸羟胺 、 sodium acetate 、 乙酸酐 作用下， 以 乙醇 、 xylene 为溶剂， 反应 15.0h， 生成 4-cyano-7-methoxy-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Joshi, S. D.; Usgaonkar, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 5, p. 399 - 402

  摘要：

  DOI：

文献信息

• Use of 4-Cyanocoumarins as Dienophiles in a Facile Synthesis of Highly Substituted Dibenzopyranones
  作者：Michael E. Jung、Damian A. Allen

  DOI：10.1021/ol802792g

  日期：2009.2.5

  A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.
• JOSHI, S. D.;USGAONKAR, R. N., INDIAN J. CHEM., 1982, 21, N 5, 399-402
  作者：JOSHI, S. D.、USGAONKAR, R. N.

  DOI：——

  日期：——
• Synthesis and rat lens aldose reductase inhibitory activity of some benzopyran-2-ones
  作者：Abram N. Brubaker、Jack De Ruiter、William L. Whitmer

  DOI：10.1021/jm00156a031

  日期：1986.6

  A number of 4,7-disubstituted benzopyran-2-ones were synthesized and evaluated for crude rat lens aldose reductase inhibitory activity. Substituents on position 4 included CH3, CO2H, CH2CO2H, CH = CHCO2H, and CH2CH2CO2H. The aromatic substituents included OH, OCH3, OCOCH3, CH2CH3, and Cl. Also included in the study were 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic, 2-oxo-2H-naphtho[1,2-b]pyran-4-acetic, and 1-naphthylacetic acids. The benzopyran and naphthopyran derivatives were prepared by the classical von Pechmann reaction. General structure-activity relationships reveal that optimal enzyme inhibitory activity is displayed by those compounds possessing the acetic acid moiety. For example, the most potent derivative, 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic acid with an IC50 of 0.020 microM, is as potent as sorbinil (IC50 = 0.017 microM) in the crude rat lens aldose reductase assay.
• Joshi, S. D.; Usgaonkar, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 5, p. 399 - 402
  作者：Joshi, S. D.、Usgaonkar, R. N.

  DOI：——

  日期：——