4-甲酰基-7-甲氧基-2-甲基苯并[b]呋喃 | 130627-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 4-甲酰基-7-甲氧基-2-甲基苯并[b]呋喃
• 英文名称: 4-formyl-7-methoxy-2-methylbenzofuran
• 英文别名: 7-methoxy-2-methylbenzofuran-4-carbaldehyde；7-methoxy-2-methylbenzo[b]furan-4-carboxaldehyde；7-methoxy-2-methyl-1-benzofuran-4-carbaldehyde
• CAS: 130627-28-0
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: DXXWUIJGUQBVFS-UHFFFAOYSA-N

物化性质

• 沸点：
  331.5±37.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲酰基-7-甲氧基-2-甲基苯并[b]呋喃 在 sodium hydroxide 、 溶剂黄146 作用下， 以 乙二醇乙醚 、 乙醇 、 水 为溶剂， 反应 0.08h， 生成 2-<4-(7-methoxy-2-methylbenzofuranyl)>-4-(3,4-methylenedioxyphenyl)-4-oxobutyronitrile
  参考文献：
  名称：

  Studies on the Chemical Constituents of Rutaceous Plants. Part LXXIII. Total Synthesis of Chelerythrine, a Benzo(c)phenanthridine Alkaloid.

  摘要：

  利用我们的新颖合成方法，包括CsF介导的芳基炔丙基醚克莱森重排为2-甲基苯并呋喃以及呋喃环氧化裂解为水杨醛，完成了苯并[c]菲啶生物碱白屈菜赤碱的全合成。通过图3所示的两条路线制备的共同中间体(5)。

  DOI：

  10.1248/cpb.40.2002
• 作为产物：
  描述：

  苯(甲)醛,3-羟基-4-甲氧基-2-(2-丙烯基)- 在 氧气 、 copper dichloride 、 palladium dichloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 以76%的产率得到4-甲酰基-7-甲氧基-2-甲基苯并[b]呋喃
  参考文献：
  名称：

  One-pot access to 2-naphthols and benzofurans via the aerobic Wacker-type oxidation/intramolecular aldol cyclization

  摘要：

  An aerobic Wacker-type oxidation/intramolecular aldol cyclization synthetic route toward two oxygenated 2-naphthols 3 and benzofurans 4 starting with skeleton 2 with good yields is described. The route has been carried by the one-pot transformation of the regioselective PdCl2/CuCl2-mediated Wacker oxidative cyclization of skeleton 2 with molecular oxygen under the alkaline methanolic condition. Skeleton 2 was prepared from skeleton 1 in moderate total yields via the known protocol. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.009

文献信息

• NOVEL HETEROCYCLIC COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS: PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Gharat Laxmikant Atmaram

  公开号：US20090306082A1

  公开（公告）日：2009-12-10

  The present invention relates to novel Phosphodiesterase type 4 (PDE4) inhibitors of the formula (1) and analogs, tautomers, enantiomers, a diasteromers, regioisomers, stereoisomers, polymorphs, pharmaceutically acceptable salts, appropriate N-oxides, pharmaceutically acceptable solvates thereof and the pharmaceutical compositions containing them which are useful in the treatment of allergic and inflammatory diseases including asthma, chronic bronchitis, atopic dermatitis, urticaria, allergic rhinitis, allergic conjunctivitis, vernal conjunctivitis, eosinophilic granuloma, psoriasis, rheumatoid arthritis, septic shock, ulcerative colitis, Crohn's disease, reperfusion injury of the myocardium and reperfusion injury of the brain, chronic glomerulonephritis, endotoxic shock and adult respiratory distress syndrome.

  本发明涉及新型磷酸二酯酶4型（PDE4）抑制剂的化学式（1）及其类似物、互变异构体、对映异构体、二对映异构体、位置异构体、立体异构体、多晶型、药学上可接受的盐、适当的N-氧化物、药学上可接受的溶剂化合物以及含有它们的制药组合物，这些制剂在治疗过敏性和炎症性疾病方面具有用途，包括哮喘、慢性支气管炎、特应性皮炎、荨麻疹、过敏性鼻炎、过敏性结膜炎、春季结膜炎、嗜酸性肉芽肿、牛皮癣、类风湿性关节炎、脓毒性休克、溃疡性结肠炎、克罗恩病、心肌再灌注损伤和脑再灌注损伤、慢性肾小球肾炎、内毒素休克和成人呼吸窘迫综合症。
• Synthetic Studies on Naturally Occurring Coumarins. I. A Convenient Synthesis of 5,8-Dimethoxy- and 7,8-Dimethoxycoumarins.
  作者：Hisashi ISHII、Kazuhiro KENMOTSU、Werner DOPKE、Takashi HARAYAMA

  DOI：10.1248/cpb.40.1770

  日期：——

  The coumarin isolated from Ariemisia carvifolia WALL was proved synthetically to be 7, 8-dimethoxycoumarin and not 5, 8-dimethoxycoumarin as previously proposed. 3, 4-Dimethoxy- and 3, 6-dimethoxysalicylaldehydes gave the corresponding coumarins in good yield by the method using phosphorane reagent in N, N-diethylaniline under reflux.

  从Ariemisia carvifolia WALL中分离出的香豆素经过合成证明为7, 8-二甲氧香豆素，而非之前提出的5, 8-二甲氧香豆素。通过在回流条件下使用在N, N-二乙基苯胺中反应的磷烷试剂，3, 4-二甲氧基和3, 6-二甲氧基香草醛得到了相应的香豆素，产率良好。
• Total Synthesis of Lemaireocereine.
  作者：Hisashi ISHII、Tsutomu ISHIKAWA、Shuji OHTA、Masahiro SUZUKI、Takashi HARAYAMA

  DOI：10.1248/cpb.40.1993

  日期：——

  By utilizing newly developed synthetic methods i.e. 2-methylbenzofuran formation by CsF-mediated Claisen rearrangement of an aryl propargyl ether and its transformation to a salicylaldehyde by oxidative cleavage of the furan ring, total synthesis of a coctus alkaloid, lemaireocereine (2), was accomplished via ten steps from the aldehyde (4) in 22% yield.

  利用新开发的合成方法，即通过 CsF 介导的芳基丙炔醚克莱森重排形成 2-甲基苯并呋喃，并通过呋喃环的氧化裂解将其转化为水杨醛，通过十个步骤从醛 (4) 完全合成了一种牛肝菌生物碱--来甲瑞林 (2)，收率为 22%。
• Cesium fluoride-mediated claisen rearrangement of aryl propargyl ether and its application to the synthesis of chelerythrine.
  作者：Hisashi ISHII、Tsutomu ISHIKAWA、Sunao TAKEDA、Satoshi UEKI、Masahiro SUZUKI、Takashi HARAYAMA

  DOI：10.1248/cpb.38.1775

  日期：——

  In the presence of cesium fluoride, the Claisen rearrangement of aryl propargyl ethers selectively provided 2-methylbenzofurans, which was successively treated with osmium tetroxide, periodic acid and 5% sodium hydroxide to give salicylaldehydes in good yields. The method was used to synthesize chelerythrine (2) via the common intermediate (8) prepared by the two routes as shown in Chart 3.

  在氟化铯存在下，芳基丙炔醚的克莱森重排选择性地提供了 2-甲基苯并呋喃，依次用四氧化锇、定期酸和 5%氢氧化钠处理后得到水杨醛，收率很高。如图 3 所示，该方法通过两种路线制备的共同中间体 (8) 合成了白屈菜红碱 (2)。
• Benzofuran-4-carboxamides
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：US06211203B1

  公开（公告）日：2001-04-03

  Compounds of formula I wherein R1 is 1-2C-alkoxy optionally substituted by flourine, R2 is methyl, 1-methylethyl, 3-7C-cycloalkyl or 3-7Ccycloalkylmethyl and Ar is a pyridyl which is optionally di-halo substituted.

  式I中的化合物，其中R1是1-2C-烷氧基，可以选择性地被氟取代，R2是甲基，1-甲基乙基，3-7C-环烷基或3-7C-环烷基甲基，Ar是一种吡啶基，可以选择性地被二卤取代。