ethyl 8-methoxy-2-methyl-4-oxo-4H-benzopyran-3-carboxylate | 367526-67-8

• 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: ethyl 8-methoxy-2-methyl-4-oxo-4H-benzopyran-3-carboxylate
• 英文别名: ethyl 8-methoxy-2-methyl-4-oxo-4H-chromene-3-carboxylate；Ethyl 8-methoxy-2-methyl-4-oxochromene-3-carboxylate
• CAS: 367526-67-8
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: QHZHJHVFPHSBGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 8-methoxy-2-methyl-4-oxo-4H-benzopyran-3-carboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以83%的产率得到8-methoxy-2-methyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  A HIGHLY PRACTICAL ROUTE TO 2-METHYLCHROMONES FROM 2-ACETOXYBENZOIC ACIDS

  摘要：

  2-Methylchromones were accessed via a keto ester condensation on 2-acetoxybenzoyl chloride, followed by cyclization and decarboxylation. No column chromatography was required in the process.

  DOI：

  10.1081/scc-100104333
• 作为产物：
  描述：

  3-甲氧基水杨酸 在 氯化亚砜 、 乙醇 、 magnesium 、 尿素 作用下， 以 吡啶 、 四氯化碳 、 乙醚 、 甲苯 为溶剂， 反应 15.5h， 生成 ethyl 8-methoxy-2-methyl-4-oxo-4H-benzopyran-3-carboxylate
  参考文献：
  名称：

  A HIGHLY PRACTICAL ROUTE TO 2-METHYLCHROMONES FROM 2-ACETOXYBENZOIC ACIDS

  摘要：

  2-Methylchromones were accessed via a keto ester condensation on 2-acetoxybenzoyl chloride, followed by cyclization and decarboxylation. No column chromatography was required in the process.

  DOI：

  10.1081/scc-100104333

文献信息

• Controllable Rh(III)-Catalyzed Annulation between Salicylaldehydes and Diazo Compounds: Divergent Synthesis of Chromones and Benzofurans
  作者：Peng Sun、Shang Gao、Chi Yang、Songjin Guo、Aijun Lin、Hequan Yao

  DOI：10.1021/acs.orglett.6b03355

  日期：2016.12.16

  A Rh(III)-catalyzed annulation between salicylaldehydes and diazo compounds with controllable chemoselectivity is described. AgNTf2 favored benzofurans via a tandem C–H activation/decarbonylation/annulation process, while AcOH led to chromones through a C–H activation/annulation pathway. The reaction exhibited good functional group tolerance and scalability. Moreover, only a single regioisomer of benzofuran

  描述了Rh（III）催化的水杨醛和重氮化合物之间具有可控的化学选择性的环化反应。AgNTf 2通过串联的C–H活化/脱羰/环化过程有利于苯并呋喃，而AcOH通过C–H活化/环化途径生成色酮。该反应表现出良好的官能团耐受性和可扩展性。此外，由于原位脱羰取向作用，仅获得了单一的苯并呋喃的区域异构体。
• On-Water Cp*Ir(III)-Catalyzed C–H Functionalization for the Synthesis of Chromones through Annulation of Salicylaldehydes with Diazo-Ketones
  作者：Suvankar Debbarma、Md Raja Sk、Biswabrata Modak、Modhu Sudan Maji

  DOI：10.1021/acs.joc.9b00418

  日期：2019.5.17

  A high-valent Ir(III)-catalyzed C–H bond functionalization is carried out for the first time on water for the synthesis of a biologically relevant chromone moiety. The C–H activation and annulation of salicylaldehydes with diazo-compounds provided the desired chromones. The synthesis of C3-substitution-free chromones has also been demonstrated by a one-pot decarboxylation by employing tert-butyl diazoester

  首次在水上进行高价Ir（III）催化的C–H键官能化，以合成生物学相关的色酮部分。水杨醛与重氮化合物的CH活化和环化提供了所需的色酮。通过使用叔丁基重氮酯进行一锅脱羧也证明了不含C 3取代的色酮的合成。产物色酮的C3和C5 C–H活化也可在不同条件下进行，以进一步多样化。
• A HIGHLY PRACTICAL ROUTE TO 2-METHYLCHROMONES FROM 2-ACETOXYBENZOIC ACIDS
  作者：Jae-Chul Jung、Jong-Pil Min、Oee-Sook Park

  DOI：10.1081/scc-100104333

  日期：2001.1

  2-Methylchromones were accessed via a keto ester condensation on 2-acetoxybenzoyl chloride, followed by cyclization and decarboxylation. No column chromatography was required in the process.