methyl 3-hydroxy-6-methoxy-2-benzofurancarboxylate | 33562-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: methyl 3-hydroxy-6-methoxy-2-benzofurancarboxylate
• 英文别名: (hydroxy-3 methoxy-6 benzofuryl-2)-carboxylate de methyle；methyl 3-hydroxy-6-methoxybenzofuran-2-carboxylate；Methyl-3-hydroxy-6-methoxybenzofuran-2-carboxylat；3-hydroxy-6-methoxy-benzofuran-2-carboxylic acid methyl ester；3-Hydroxy-6-methoxy-2-benzofurancarboxylic acid methyl ester；methyl 3-hydroxy-6-methoxy-1-benzofuran-2-carboxylate
• CAS: 33562-13-9
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: QBMXZHYGSLKOSF-UHFFFAOYSA-N

物化性质

• 熔点：
  94 °C
• 沸点：
  327.9±37.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-hydroxy-6-methoxy-2-benzofurancarboxylate 生成 Methyl 6-methoxy-3-phenylmethoxy-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  CONNOR, DAVID T.;CETENKO, WIACZESLAW A.;UNANGST, PAUL C.;JOHNSON, ELIZABE+

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基水杨酸甲酯 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 methyl 3-hydroxy-6-methoxy-2-benzofurancarboxylate
  参考文献：
  名称：

  Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents

  摘要：

  The synthesis and antiallergic activity of a series of novel benzothiophene-, benzofuran-, and naphthalenecarbox-amidotetrazoles are described. A number of the compounds inhibit the release of histamine from anti-IgE stimulated basophils obtained from allergic donors. Optimal inhibition is exhibited in benzothiophenes with a 3-alkoxy substituent in combination with a 5-methoxy, 6-methoxy, or a 5,6-dimethoxy group. Compounds 13c (CI-959) also inhibited respiratory burst of human neutrophils and the release of mediators from anti-IgE-stimulated human chopped lung.

  DOI：

  10.1021/jm00083a023

文献信息

• Transition Metal‐Catalyzed Synthesis of 3‐Coumaranone‐Containing NH‐Aziridines from 2 <i>H</i> ‐Azirines: Nickel(II) versus Gold(I)
  作者：Pavel A. Sakharov、Nikolai V. Rostovskii、Alexander F. Khlebnikov、Olesya V. Khoroshilova、Mikhail S. Novikov

  DOI：10.1002/adsc.201900366

  日期：2019.7.11

  catalytic nucleophilic addition reaction of 3‐hydroxybenzofuran‐2‐carboxylic acid derivatives to 2H‐azirines for the high‐yield synthesis of NH‐aziridines with a 3‐coumaranone substituent has been developed. The Ph3PAuNTf2‐catalyzed reaction is diastereoselective to give predominantly (RS,SR)‐isomer of aziridine in good yield. The Ni(hfacac)2‐catalyzed reaction affords aziridines in up to 98% yield and low

  已开发出3-羟基苯并呋喃-2-羧酸衍生物与2 H-叠氮基的亲核催化加成反应，可高产合成带有3-coumaranone取代基的NH-氮丙啶。Ph 3 PAuNTf 2催化的反应是非对映选择性的，主要以高收率得到氮丙啶的（RS，SR）-异构体。Ni（hfacac）2催化反应可提供氮丙啶，产率高达98％，低或中等非对映选择性，在某些情况下与金（I）催化反应相反。Ph 3 PAuNTf 2对于受位阻的叠氮基以及带有吸电子基团的苯并呋喃，其效果很好，而Ni（hfacac）2是制备具有重氮乙酰基取代基的氮丙啶的首选催化剂。后一种化合物可以用作通过布氏环扩环反应合成稠合氮丙啶的底物。
• Benzothiophenes and benzofurans and antiallergic use thereof
  申请人：Warner-Lambert Company

  公开号：US04703053A1

  公开（公告）日：1987-10-27

  Novel benzothiophene and benzofuran derivatives having antiallergic activity are described as well as a method of manufacture, pharmaceutical compositions, and methods of use therefor. The disclosure describes the use of derivatives for prevention of the release of mediators including histamine and leukotrienes from basophils and mast cells, and prevent respiratory burst in neutrophils providing activity useful in cardiovascular disorders as well as in antiinflammatory, psoriasis, and antimigraine treatment.

  本发明涉及具有抗过敏活性的新型苯并噻吩和苯并呋喃衍生物，以及制备方法、药物组合物和使用方法。本发明描述了使用衍生物预防嗜碱性粒细胞和肥大细胞释放组织胺和白三烯等介质，并防止嗜中性粒细胞呼吸爆发，从而提供在心血管疾病、抗炎、银屑病和抗偏头痛治疗中有用的活性。
• Synthetic Models Related to Methoxalen – CYP2A6 Interactions. Dimethoxybenzofuran Derivatives as Potent and Selective Inhibitors of CYP2A6
  作者：Kazuaki Oda、Yuki Yamaguchi、Ichie Akimoto、Teruki Yoshimura、Keiji Wada、Naozumi Nishizono、Kyoko Motegi

  DOI：10.3987/com-13-12744

  日期：——

  The human CYP2A6 enzyme metabolizes several xenobiotics including nicotine, the addictive component in tobacco. Reduced activity of CYP2A6, either for genetic reasons or by administering inhibitors of CYP2A6, reduces tobacco smoking. The reported compound methoxalen had a potent inhibitory effect on activity of CYP2A6 with an IC50 value of 1.27 mu M. We selected methoxalen as a lead compound and prepared various dimethoxybenzofuran derivatives that have inhibitory effects on activity of human cytochrome P450 (CYP) 2A6. Synthetic benzofuran derivatives (3,6-dimethoxybenzofuran: IC50=1.92 mu M and 3,7-dimethoxybenzofuran: IC50=2.00 mu M) also exhibited comparable activities against CYP2A6 and were selective inhibitors of CYP2A6. These compounds can be used as lead compounds in the development of drugs for smoking reduction therapy.
• WO2008/74445
  申请人：——

  公开号：——

  公开（公告）日：——
• LAMOTTE G.; DEMERSEMAN P.; ROYER R.; GAYRAL PH.; FOURNIAT J., EUR. J. MED. CHEM., 21,(1986) N 5, 379-383
  作者：LAMOTTE G.、 DEMERSEMAN P.、 ROYER R.、 GAYRAL PH.、 FOURNIAT J.

  DOI：——

  日期：——