7-methoxy-3-methylchromone | 54031-60-6

• 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: 7-methoxy-3-methylchromone
• 英文别名: 7-methoxy-3-methyl-4H-chromen-4-one；7-Methoxy-3-methylchromen-4-one
• CAS: 54031-60-6
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: HEJUALWBJBXIJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-methylchromone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 12.0h， 生成 3-(1H-imidazol-1-ylmethyl)-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Exploiting the Chromone Scaffold for the Development of Inhibitors of Corticosteroid Biosynthesis

  摘要：

  The inhibition of corticosteroid biosynthesis could be considered as an emerging strategy to reduce their abnormally high levels, and in this framework CYP11B1 and CYP11B2 represent the most promising targets. In continuing our studies on flavonoid-like scaffolds as privileged structures in medicinal chemistry, in this paper we describe a small library of pyridyl- and imidazolylmethylchromones as potential inhibitors of these enzymes. Testing results proved that position 3 of the chromone scaffold is the most favorable for the introduction of the heme-coordinating heterocycles and, among them, the 4-imidazolyl moiety is the most convenient for the interaction with the heme iron of the selected cytochromes. A low nanomolar inhibitor of CYP11B1 (5c) was obtained) endowed with reasonable selectivity toward CYP11B2 and able to better discriminate with respect to CYP17 and CYP19.

  DOI：

  10.1021/acs.jmedchem.5b01609
• 作为产物：
  描述：

  4-methoxy-2-(prop-2-yn-1-yloxy)benzaldehyde 在 potassium tert-butylate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 1,4-二氧六环 、 甲醇 、 叔丁醇 为溶剂， 生成 7-methoxy-3-methylchromone
  参考文献：
  名称：

  系链长度控制的同系异戊烯基苯甲醛的不同反应性：苯醌与二甲苯的形成

  摘要：

  描述了作为环化底物的两种同系异位烯醛的发散行为，即2-（buta-2,3-dienyloxy）-和2-（propa-1,2-dienyloxy）苯甲醛。2-（Buta-2,3-dienyloxy）benzaldehydes经历正式的烯丙基碳环化反应以提供色烯，而2-（propa-1,2-dienyloxy）benzaldehydes反应生成色酮。色烯的形成严格来说是一个正式的加氢芳构化过程，分为两个部分，即艾伦Claisen型重排和氧环化。必须调用未知的N杂环卡宾（NHC）催化的烯丙基加氢酰化反应来说明色酮的制备。邻位带有给电子取代基或吸电子取代基的烯丙基苯甲醛可以很好地提供加氢芳基化和加氢酰化产物。反应性的这种意想不到的差异可以通过密度泛函理论计算来合理化。

  DOI：

  10.1002/chem.201404516

文献信息

• Synthesis of Tetrasubstituted Enamines through Borane-Catalyzed Hydrogenations
  作者：Zijia Zhang、Xiangqing Feng、Haifeng Du

  DOI：10.1021/acs.orglett.3c03578

  日期：2023.12.29

  This paper describes a B(C6F5)3-catalyzed hydrogenation of β-substituted α,β-unsaturated imines by using as low as 0.2 mol % catalyst. A variety of tetrasubstituted enamines were afforded in 95–99% yields. It provides an efficient and facile way without the need for column chromatography purification.

  本文描述了使用低至0.2 mol% 的催化剂进行B(C 6 F 5 ) 3催化的β-取代的α,β-不饱和亚胺的氢化反应。多种四取代烯胺的产率达到 95-99%。它提供了一种有效且简便的方法，无需柱色谱纯化。
• Legrand, Bulletin de la Societe Chimique de France, 1959, p. 1599,1602
  作者：Legrand

  DOI：——

  日期：——
• Da Re et al., Annali di Chimica, 1959, vol. 49, p. 2089,2095
  作者：Da Re et al.

  DOI：——

  日期：——
• Jain, A. C.; Tyagi, O. D.; Saksena, Rene, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 678 - 679
  作者：Jain, A. C.、Tyagi, O. D.、Saksena, Rene

  DOI：——

  日期：——
• Exploiting the Chromone Scaffold for the Development of Inhibitors of Corticosteroid Biosynthesis
  作者：Silvia Gobbi、Qingzhong Hu、Christina Zimmer、Matthias Engel、Federica Belluti、Angela Rampa、Rolf W. Hartmann、Alessandra Bisi

  DOI：10.1021/acs.jmedchem.5b01609

  日期：2016.3.24

  The inhibition of corticosteroid biosynthesis could be considered as an emerging strategy to reduce their abnormally high levels, and in this framework CYP11B1 and CYP11B2 represent the most promising targets. In continuing our studies on flavonoid-like scaffolds as privileged structures in medicinal chemistry, in this paper we describe a small library of pyridyl- and imidazolylmethylchromones as potential inhibitors of these enzymes. Testing results proved that position 3 of the chromone scaffold is the most favorable for the introduction of the heme-coordinating heterocycles and, among them, the 4-imidazolyl moiety is the most convenient for the interaction with the heme iron of the selected cytochromes. A low nanomolar inhibitor of CYP11B1 (5c) was obtained) endowed with reasonable selectivity toward CYP11B2 and able to better discriminate with respect to CYP17 and CYP19.