8-Methyl-3-oxo-3,8-dihydro-1H-indeno<1,2-c>furan | 124583-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 8-Methyl-3-oxo-3,8-dihydro-1H-indeno<1,2-c>furan
• 英文别名: 3-oxo-8-methyl-1H,3H-indeno<1,2-c>furan；4-Methyl-3,4-dihydroindeno[1,2-c]furan-1-one
• CAS: 124583-42-2
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: QJPDYFGFYYPAKU-UHFFFAOYSA-N

物化性质

• 沸点：
  422.9±34.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-Methyl-3-oxo-3,8-dihydro-1H-indeno<1,2-c>furan 生成 4-Methyl-3,3a,4,8b-tetrahydroindeno[1,2-c]furan-1-one
  参考文献：
  名称：

  Kasper Annette M., Nash John J., Morrison Harry, J. Org. Chem, 59 (1994) N 10, S 2792-2798

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Butynyl phenylacetate 在 rhodium(II) octanoate sodium hydride 、 甲烷磺酰基叠氮化物 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 8-Methyl-3-oxo-3,8-dihydro-1H-indeno<1,2-c>furan
  参考文献：
  名称：

  Rhodium(II)-catalyzed cyclization of 2-alkynyl 2-diazo-3-oxobutanoates as a method for synthesizing substituted furans

  摘要：

  A series of 2-alkynyl 2-diazo-3-oxobutanoates, when treated with a catalytic quantity of rhodium(II) acetate, were found to produce furo[3,4-c]furans in good yield. The reaction proceeds by addition of a rhodium-stabilized carbenoid onto the acetylenic pi-bond to give a vinyl carbenoid which subsequently cyclizes onto the neighboring carbonyl group to produce the furan ring. In a similar manner, indeno[1,2-c]furans were produced from 2-butynyl 2-diazoarylacetates. Compounds substituted with methyl groups on the propargylic carbon atom cyclized at a slower rate. This rate diminution is attributed to the fact that the unsubstituted propargyl group can more easily achieve the required conformation for cyclization. C-H insertion was found to compete with furan formation when an alkyl group was attached to the keto functionality of the starting diazo acetoacetate. Diazo alkynyl sulfones undergo a novel oxygen transfer reaction when treated with rhodium(II) acetate at 80-degrees-C. The cyclized product is formed by sulfone oxygen attack onto the vinyl carbenoid producing a dipolar species which subsequently collapses to give the butenolide sulfoxide.

  DOI：

  10.1021/jo00053a009

文献信息

• Rhodium(II)-catalyzed cyclization of 2-alkynyl 2-diazo-3-oxobutanoates as a method for synthesizing substituted furans
  作者：Albert Padwa、Frederick R. Kinder

  DOI：10.1021/jo00053a009

  日期：1993.1

  A series of 2-alkynyl 2-diazo-3-oxobutanoates, when treated with a catalytic quantity of rhodium(II) acetate, were found to produce furo[3,4-c]furans in good yield. The reaction proceeds by addition of a rhodium-stabilized carbenoid onto the acetylenic pi-bond to give a vinyl carbenoid which subsequently cyclizes onto the neighboring carbonyl group to produce the furan ring. In a similar manner, indeno[1,2-c]furans were produced from 2-butynyl 2-diazoarylacetates. Compounds substituted with methyl groups on the propargylic carbon atom cyclized at a slower rate. This rate diminution is attributed to the fact that the unsubstituted propargyl group can more easily achieve the required conformation for cyclization. C-H insertion was found to compete with furan formation when an alkyl group was attached to the keto functionality of the starting diazo acetoacetate. Diazo alkynyl sulfones undergo a novel oxygen transfer reaction when treated with rhodium(II) acetate at 80-degrees-C. The cyclized product is formed by sulfone oxygen attack onto the vinyl carbenoid producing a dipolar species which subsequently collapses to give the butenolide sulfoxide.
• Preparation of oxygenated heterocycles via the cyclization reaction of α-diazo substituted alkynes
  作者：Frederick R. Kinder、Albert Padwa

  DOI：10.1016/s0040-4039(00)97184-3

  日期：1990.1
• Generation of vinylcarbenes by the intramolecular addition of .alpha.-diazo ketones to acetylenes
  作者：Albert Padwa、Ugo Chiacchio、Yves Garreau、Jamal M. Kassir、Keith E. Krumpe、Allen M. Schoffstall

  DOI：10.1021/jo00289a006

  日期：1990.1
• PADWA, ALBERT;CHIACCHIO, UGO;GARREAU, YVES;KASSIR, JAMAL M.;KRUMPE, KEITH+, J. ORG. CHEM., 90,(1990) N, C. 414-416
  作者：PADWA, ALBERT、CHIACCHIO, UGO、GARREAU, YVES、KASSIR, JAMAL M.、KRUMPE, KEITH+

  DOI：——

  日期：——
• KINDER, FREDERICK R.;PADWA, ALBERT, TETRAHEDRON LETT., 31,(1990) N7, C. 6835-6838
  作者：KINDER, FREDERICK R.、PADWA, ALBERT

  DOI：——

  日期：——