2,3,6,7-Tetrahydro-2-butoxy-5H-1-oxainden-4-one

• 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: 2,3,6,7-Tetrahydro-2-butoxy-5H-1-oxainden-4-one
• 英文别名: 2-butoxy-3,5,6,7-tetrahydro-2H-1-benzofuran-4-one
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: LBHQHBYHHOLBTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙烯基正丁醚 、 2-diazocyclohexane-1,3-dione 在 dirhodium tetraacetate 作用下， 反应 24.0h， 以92%的产率得到2,3,6,7-Tetrahydro-2-butoxy-5H-1-oxainden-4-one
  参考文献：
  名称：

  Reactions of a Cyclic Rhodium Carbenoid with Aromatic Compounds and Vinyl Ethers

  摘要：

  Further investigation has been made of the reactions between the cyclic diazo compound 2-diazo-1,3-cyclohexanedione and aromatic heterocycles or vinyl ethers, catalyzed by rhodium carboxylates. The extraordinary reactivity of the carbenoid derived from this diazo compound is shown by its ready reaction with solvents such as dichloromethane, dichloroethane, and fluorobenzene. Detailed investigation of its reactions with furans have shown that steric interactions dominate, both in terms of regioselectivity with unsymmetrical substrates and yield. This reaction provides a useful entry to the furo[2,3-b]furan ring system found in a number of naturally-occurring compounds and is formally a 1,3-dipolar cycloaddition. Products of net C-H insertion and with reverse regiochemistry (furo[3,2-b]furan ring system) were also detected. With pyrroles and thiophenes, cycloadducts were seen in a few cases, but were generally the exception; C-H insertion products dominate these reactions. Vinyl ethers proved reliable reactants in providing dipolar cycloadducts. The results of this study have been interpreted in terms of four pathways: an initial cyclopropanation would produce a spirocyclic dicarbonyl system that on heterolytic cleavage of one of the two cyclopropane bonds would give a zwitterion. The partitioning of such a zwitterion between ring closure and proton transfer would define the ratio of C-H insertion and dipolar cycloaddition products. Both thermodynamic and stereoelectronic arguments have been advanced to explain the observations and were supported by calculations.

  DOI：

  10.1021/jo00112a036

文献信息

• Cyclohexanone derivatives and preparation thereof
  申请人：KURARAY CO., LTD.

  公开号：EP0041656A2

  公开（公告）日：1981-12-16

  Novel cyclohexanone derivatives of general formula: (wherein R1 is a hydrocarbon group of 1 to 15 carbon atoms) and new cyclohexanone derivatives of general formula: (wherein R' and R2 each is a hydrocarbon group of 1 to 15 carbon atoms) are produced by an electrooxidative coupling of 1,3-cyclohexanedione with a vinyl ether of generat formula: (wherein R1 is as defined above) in the presence or absense of an alcohol of general formula: (wherein R2 is as defined above). These new cyclohexanone derivatives can be easily converted to N-substituted or unsubstituted-4-oxo-4,5,6,7-tetrahydroindoles, which are of value as intermediates for the production of N-substituted or unsubstituted-4-hydroxyindoles and, thence, to pindolol and its analogs.

  通式如下的新型环己酮衍生物 (其中 R1 为 1 至 15 个碳原子的烃基)和通式如下的新型环己酮衍生物： (其中 R' 和 R2 各为 1 至 15 个碳原子的烃基）通过 1,3-环己二酮与通式如下的乙烯基醚的电氧化偶联生成： (其中 R1 如上定义）在通式为醇存在或不存在的情况下通过电氧化偶联生成： (其中 R2 如上定义）。这些新的环己酮衍生物可以很容易地转化为 N-取代或未取代的-4-氧代-4,5,6,7-四氢吲哚，它们是生产 N-取代或未取代的-4-羟基吲哚，进而生产吲哚及其类似物的中间体。
• SIMAYA, SIGEHRU;UMEHYAMA, KEHNDZI;ONISI, KOSI;FUDZITA, JOSIDZI;TISIGURO, +
  作者：SIMAYA, SIGEHRU、UMEHYAMA, KEHNDZI、ONISI, KOSI、FUDZITA, JOSIDZI、TISIGURO, +

  DOI：——

  日期：——
• US4336202A
  申请人：——

  公开号：US4336202A

  公开（公告）日：1982-06-22