2-(o-methoxybenzylidene)-6-methoxycoumaran-3-one | 108197-53-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: 2-(o-methoxybenzylidene)-6-methoxycoumaran-3-one
• 英文别名: (E)-2',6-dimethoxyaurone；6-Methoxy-2-[(2-methoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 108197-53-1
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: MLUQKOPOEBGRIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-苯甲酰甲基溴吡啶 、 2-(o-methoxybenzylidene)-6-methoxycoumaran-3-one 在 乙酸铵 作用下， 以 溶剂黄146 为溶剂， 以50%的产率得到7-Methoxy-4-(2-methoxy-phenyl)-2-phenyl-benzo[4,5]furo[3,2-b]pyridine
  参考文献：
  名称：

  Sarbagya, D. P.; Rangachari, K.; Mazumdar, A. K. D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 891 - 893

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲氧基-3-苯并呋喃酮 、 邻甲氧基苯甲醛 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 生成 2-(o-methoxybenzylidene)-6-methoxycoumaran-3-one
  参考文献：
  名称：

  Regioselective Synthesis of Tetrasubstituted Pyrroles by 1,3-Dipolar Cycloaddition and Spontaneous Decarboxylation

  摘要：

  We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of alpha,beta-unsaturated benzofuran-3(2h)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).

  DOI：

  10.1021/ol8022193

文献信息

• <scp>Ultrasound‐promoted</scp> 1, <scp>3‐dipolar</scp> cycloaddition of azomethine yields for synthesis of dispiropyrrolidineoxindole derivatives in hexyltriphenylphosphonium bromide as an ionic liquid, and the evaluation of their anti‐cancer activity
  作者：Firouz Matloubi Moghaddam、Nouraddin Hosseinzadeh、Fatemeh Safari、Alireza Foroumadi

  DOI：10.1002/jhet.4595

  日期：2023.3

  one-pot three-component process for the synthesis of derivatives using cycloadition catching azomethineylides in situ created by means of decarboxylative build-up of sarcosine and isatin has been developed in hexyltriphenylphosphonium bromide (HTPB) as an ionic liquid and recyclable solvent in supreme yield without the use of a catalyst under ultrasonic irradiation. This method offers mild reaction conditions

  在己基三苯基溴化磷 (HTPB) 作为离子液体中开发了一种绿色、轻松且具有保护性的一锅法三组分工艺，用于使用环加成反应原位捕获偶氮甲亚胺衍生物，该方法通过肌氨酸和靛红的脱羧作用生成和可回收溶剂，在超声波照射下无需使用催化剂即可获得最高收率。该方法提供温和的反应条件、在较短的反应时间内获得优异的产品收率、易于操作和环境友好的过程以及高比对和立体选择性。已针对四种细胞系研究了所有新化合物的抗癌活性。此外，这些结构还通过光谱技术和信号晶体 X 射线分析进行了验证。
• Proximity effects in the electron impact mass spectra of aurones and related compounds
  作者：R. J. Goldsack、J. S. Shannon

  DOI：10.1002/oms.1210151102

  日期：1980.11

  AbstractThe principal ions in the electron impact mass spectra of a series of 6‐methoxyaurones have been shown to be due to four separate reactions associated with proximity effects involving the phenyl group and the coumaran‐one residue. A detailed study with labelled derivatives has been supplemented by a study of the vinylogue 2‐cinnamylidene‐6‐methoxycoumaran‐3‐one and compounds in which the aurone phenyl group has been replaced by α‐naphthyl, β‐naphthyl and 9‐anthryl.
• Regioselective Synthesis of Tetrasubstituted Pyrroles by 1,3-Dipolar Cycloaddition and Spontaneous Decarboxylation
  作者：Yongju Kim、Jonghoon Kim、Seung Bum Park

  DOI：10.1021/ol8022193

  日期：2009.1.1

  We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of alpha,beta-unsaturated benzofuran-3(2h)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).
• Sarbagya, D. P.; Rangachari, K.; Mazumdar, A. K. D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 891 - 893
  作者：Sarbagya, D. P.、Rangachari, K.、Mazumdar, A. K. D.、Banerji, K. D.

  DOI：——

  日期：——