2--6-methoxybenzofuranone | 87931-11-1

• 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--6-methoxybenzofuranone
• 英文别名: (E)-4'-chloro-6-methoxyaurone；3(2H)-Benzofuranone, 2-[(4-chlorophenyl)methylene]-6-methoxy-；2-[(4-chlorophenyl)methylidene]-6-methoxy-1-benzofuran-3-one
• CAS: 87931-11-1
• 化学式: C₁₆H₁₁ClO₃
• 分子量: 286.715
• InChiKey: VWGPEPCJDXBXEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  2--6-methoxybenzofuranone 在 lithium aluminium tetrahydride 、 正丁基锂 、 magnesium bromide 作用下， 反应 5.0h， 生成 2-(p-Chlorobenzyl)-3-[p-(2-morpholinoethoxy)phenyl]-6-methoxy-benzo[b]furan
  参考文献：
  名称：

  An Improved Method for the Synthesis of 2-(p-Halobenzyl)-3-aryl-6-methoxybenzofurans as Selective Ligands for the Antiestrogen-Binding Sites

  摘要：

  A series of 2-(p-fluorobenzyl)-3-aryl-6-methoxybenzofurans has been prepared in good yields in a two-step sequence from the corresponding benzylidencoumaranones (aurones).

  DOI：

  10.1080/00397919308011285
• 作为产物：
  描述：

  6-甲氧基-3-苯并呋喃酮 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以260 mg的产率得到2--6-methoxybenzofuranone
  参考文献：
  名称：

  Proximity effects in the electron impact mass spectra of aurones and related compounds

  摘要：

  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by a study of the vinylogue 2‐cinnamylidene‐6‐methoxycoumaran‐3‐one and compounds in which the aurone phenyl group has been replaced by α‐naphthyl, β‐naphthyl and 9‐anthryl.

  DOI：

  10.1002/oms.1210151102

文献信息

• 2-(benzyl)-3-arylbenzofurans as antitumour and hypocholesterolemic agents
  申请人：National University of Singapore

  公开号：US05354861A1

  公开（公告）日：1994-10-11

  The synthesis and the biological evaluation of a series of basic ethers of 2-benzyl-3-arylbenzofurans as antitumor agents is described. These compounds bind significantly to the antiestrogen-binding sites but only poorly to the estrogen receptor sites and are cytotoxic to tumor cells. Some of these compounds also significantly inhibited de novo cholesterol biosynthesis in an estrogen receptor negative lymphoma cell line rich in antiestrogen-binding sites.

  本文介绍了一系列2-苄基-3-芳基苯并呋喃的碱性醚类抗肿瘤剂的合成和生物评价。这些化合物显著结合到抗雌激素结合位点，但对雌激素受体位点的结合较差，并对肿瘤细胞具有细胞毒性。其中一些化合物还显著抑制了雌激素受体阴性的富含抗雌激素结合位点的淋巴瘤细胞系中的新生胆固醇生物合成。
• <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。
• An Improved Method for the Synthesis of 2-(p-Halobenzyl)-3-aryl-6-methoxybenzofurans as Selective Ligands for the Antiestrogen-Binding Sites
  作者：Siu-Cchoon Ng、Oi-Lian Kon、Keng-Yeow Sim、Natarajan Srikanth

  DOI：10.1080/00397919308011285

  日期：1993.7

  A series of 2-(p-fluorobenzyl)-3-aryl-6-methoxybenzofurans has been prepared in good yields in a two-step sequence from the corresponding benzylidencoumaranones (aurones).
• 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.