ethyl 6-methoxy-2-methyl-4-oxo-4H-benzopyran-3-carboxylate | 367526-68-9

• 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 6-methoxy-2-methyl-4-oxo-4H-benzopyran-3-carboxylate
• 英文别名: ethyl 6-methoxy-2-methyl-4-oxo-4H-chromene-3-carboxylate；Ethyl 6-methoxy-2-methyl-4-oxochromene-3-carboxylate
• CAS: 367526-68-9
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: UOVFEBGEUJMVCN-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 6-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78%的产率得到6-methoxy-2-methyl-4H-chromen-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：

  2-Acetoxy-5-methoxy-benzoesaeure 在 氯化亚砜 、 乙醇 、 对甲苯磺酸 、 magnesium 、 尿素 作用下， 以 四氯化碳 、 水 、 甲苯 为溶剂， 反应 7.5h， 生成 ethyl 6-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。
• Cp*Ir(III)-Catalyzed C–H/O–H Functionalization of Salicylaldehydes for the Synthesis of Chromones at Room Temperature
  作者：Dhanaji M. Lade、Yogesh N. Aher、Amit B. Pawar

  DOI：10.1021/acs.joc.9b01139

  日期：2019.7.19

  C–H/O–H-bond functionalization of salicylaldehydes with α-diazocarbonyl compounds for the synthesis of chromones under redox-neutral conditions. The reaction proceeds at room temperature and displays excellent functional group tolerance along with high yields of the corresponding products. The developed reaction protocol was successfully applied for the late-stage functionalization of estrone derivative

  在这里，我们报道了Cp * Ir（III）催化的水杨醛与α-重氮羰基化合物的水合醛CH-H / O-H键官能化，用于在氧化还原中性条件下合成色酮。反应在室温下进行，显示出优异的官能团耐受性以及相应产物的高产率。所开发的反应方案已成功应用于雌酮衍生物的后期功能化。
• 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.