7-hydroxy-4-methyl-8-(morpholin-4-ylmethyl)-2H-chromen-2-one | 92647-29-5

• 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: 7-hydroxy-4-methyl-8-(morpholin-4-ylmethyl)-2H-chromen-2-one
• 英文别名: 7-hydroxy-4-methyl-8-(morpholinomethyl)-2H-chromen-2-one；4-methyl-8-(morpholin-4-ium-4-ylmethyl)-2-oxochromen-7-olate
• CAS: 92647-29-5
• 化学式: C₁₅H₁₇NO₄
• mdl: MFCD01067746
• 分子量: 275.304
• InChiKey: FTVHWJZIFKOGPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  476.5±45.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-4-methyl-8-(morpholin-4-ylmethyl)-2H-chromen-2-one 在 N,N-二甲基乙酰胺 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 15.83h， 生成 8-allyl-7-hydroxy-4-methylcoumarin
  参考文献：
  名称：

  Ghantwal; Samant, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 11, p. 1242 - 1247

  摘要：

  DOI：
• 作为产物：
  描述：

  羟甲香豆素 以59%的产率得到
  参考文献：
  名称：

  CASCAVAL, AL.;NICOLAESCU, TATIANA;BIBIAN-CILIANU, ST.;ZANOAGA, CRISTINEL +, BUL. INST. POLITEHN. IASI. SEC. 2, 35,(1989) N-4, C. 77-80

  摘要：

  DOI：

文献信息

• The reaction of 4-aminocoumarin with β-carbonyl-substituted 4Н-chromenes: synthesis of 5H-chromeno[4,3-b]pyridin-5-one derivatives
  作者：Dmitriy V. Osipov、Alina A. Artyomenko、Vitaly A. Osyanin、Yuri N. Klimochkin

  DOI：10.1007/s10593-019-02451-3

  日期：2019.3

  1Н-benzo[f]chromene-3-carbaldehydes with 4-aminocoumarin were used to obtain a series of pyridocoumarin derivatives containing a 2-hydroxybenzyl or 2-hydroxy-1-naphthyl substituent at the β-position relative to the nitrogen atom. The reaction mechanism includes a Michael reaction, chromane ring opening, and cyclodehydration.

  的4个反应Н色烯-3- carbaldehydes和1 Н -苯并[ ˚F ]色烯-3- carbaldehydes与4-氨基香豆素被用来获取一系列含有2-羟基苄基或2-羟基-1-萘基取代基pyridocoumarin衍生物的相对于氮原子的β位。反应机理包括迈克尔反应，苯并二氢吡喃开环和环脱水。
• The synthesis of 3-nitro-4H-benzo[h]chromenes
  作者：Dmitry V. Osipov、Alina A. Artemenko、Pavel E. Krasnikov、Vitaly A. Osyanin

  DOI：10.1007/s10593-023-03189-9

  日期：2023.5

  A method for the synthesis of 3-nitro-4H-benzo[h]chromenes was developed based on the reaction of 1-naphthoquinone 2-methides generated in situ from Mannich bases with 4-(2-nitrovinyl)morpholine. It was shown that such nucleophiles as morpholine and 4-bromoaniline add to the double bond of the pyran ring.

  基于曼尼希碱原位生成的1-萘醌2-甲基化物与4-(2-硝基乙烯基)吗啉的反应，开发了一种合成3-硝基-4H-苯并[ h ]色烯的方法。结果表明，诸如吗啉和4-溴苯胺之类的亲核试剂会加成到吡喃环的双键上。
• Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae
  作者：Mauro Mazzei、Erika Nieddu、Mariangela Miele、Alessandro Balbi、Marco Ferrone、Maurizio Fermeglia、Marco T. Mazzei、Sabrina Pricl、Paolo La Colla、Fabio Marongiu、Cristina Ibba、Roberta Loddo

  DOI：10.1016/j.bmc.2007.11.045

  日期：2008.3

  Some Mannich bases of 7-hydroxycoumarin (2) and their simple derivatives (3 and 4) were prepared and tested against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). This study was directed toward Flaviviridae and, in particular, HCV surrogate viruses (BVDV, YFV). The 7-hydroxy derivatives 2 were generally devoid of activity, but when position 7 was propylated, the resulting 7-propyloxy derivatives 3 were in some cases endowed with an interesting activity against BVDV. The formation of 7-benzoyl derivatives 4 gave compounds generally lacking in activity against Flaviviridae, whereas the appearance of activity against RSV has been observed. Also some unsymmetrical methylene derivatives 5-7 (namely coumarins bridged to chromones or indoles) were found moderately active in antiviral tests. Derivatives 3 were submitted to a molecular modeling study using DNA polymerase of HCV as a target. The good correlation between calculated molecular modeling IC50 and experimental EC50 indicates that DNA polymerase is potentially involved in the inhibition of surrogate HCV viruses. (C) 2007 Elsevier Ltd. All rights reserved.
• NICOLAESCU, TATIANA, BUL. INST. POLITEHN. IASI., 33,(1987) N 1-4, 53-55
  作者：NICOLAESCU, TATIANA

  DOI：——

  日期：——
• CASCAVAL, ALEXANDRU;OFENBERG, HARY;NICOLAESCU, TATIANA;APOSTOL, MIHAI;CLO+
  作者：CASCAVAL, ALEXANDRU、OFENBERG, HARY、NICOLAESCU, TATIANA、APOSTOL, MIHAI、CLO+

  DOI：——

  日期：——