1-(1-oxo-1H-1-inden-3-yl)-5-methylbicyclo<3.1.0>hexane | 123432-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1-(1-oxo-1H-1-inden-3-yl)-5-methylbicyclo<3.1.0>hexane
• 英文别名: 3-(5-Methyl-1-bicyclo[3.1.0]hexanyl)-inden-1-one；3-(5-methyl-1-bicyclo[3.1.0]hexanyl)inden-1-one
• CAS: 123432-04-2
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: PDPDHOMXKIUCHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  343.7±25.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  邻溴苯甲酸甲酯 在 rhodium(II) acetate dimer bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 oxonium 、 potassium trimethylsilonate 、 三乙胺 、 氯甲酸甲酯 、 三苯基膦 作用下， 以 苯 为溶剂， 生成 1-(1-oxo-1H-1-inden-3-yl)-5-methylbicyclo<3.1.0>hexane
  参考文献：
  名称：

  通过分子内将乙二氮酮添加到炔属pi键上形成环烯酮

  摘要：

  用乙酸铑（II）处理几种邻炔基取代的α-二重氮苯乙酮衍生物导致分子内加成到乙炔π-键上，得到瞬态的环丙烯，该环丙烯自发地重排成乙烯基卡宾中间体。

  DOI：

  10.1016/s0040-4039(00)99084-1

文献信息

• Rhodium(II)-catalyzed cyclization reactions of alkynyl-substituted .alpha.-diazo ketones
  作者：Albert Padwa、Keith E. Krumpe、Yves Gareau、Ugo Chiacchio

  DOI：10.1021/jo00007a047

  日期：1991.3

  Treatment of several omicron-alkynl-substituted alpha-diazoacetophenone derivatives with rhodium (II) carboxylates results in the formation of substituted indenones. The simplest mechanism accounting for the results involves addition of a rhodium-stabilized carbenoid onto the acetylenic pi-bond to generate a vinyl carbenoid directly of possibly a highly strained cyclopropene derivative. The vinyl carbenoid was found to undergo addition to a neighboring alkene tethered on the side chain to give an indenyl-substituted bicyclo[3.1.0]hexane derivative. A number of related systems were examined so as to probe the scope and generality of the process. Treatment of omicron-(6,8-nonadien-1-ynyl)-alpha-diazoacetophenone with rhodium (II) mandelate afforded a cyclopent[g]azulenone derivative. The formation of this compound involves a divinylcyclopropane intermediate that readily undergoes a Cope rearrangement under the reaction conditions. The rhodium-catalyzed reaction of 2-(6-oxo-1-hepty-nyl)-alpha-diazoacetophenone in the presence of N-phenylmaleimide afforded a mixture of two cycloadducts. One of the products can be accounted for in terms of a cyclization of the vinyl carbenoid onto the oxygen atom of the neighboring carbonyl group to give a resonance-stabilized dipole. 1,3-Dipolar cycloaddition of the carbonyl ylide across the activated pi-bond of N-phenylmaleimide affords the observed product. The second cycloadduct is formed by a 1,2-hydrogen shift of the initially produced vinyl carbenoid. The resulting diene undergoes a subsequent Diels-Alder reactions with N-phenylmaleimide.
• PADWA, ALBERT;KRUMPE, KEITH E.;ZHI, LIN, TETRAHEDRON LETT., 30,(1989) N0, C. 2633-2636
  作者：PADWA, ALBERT、KRUMPE, KEITH E.、ZHI, LIN

  DOI：——

  日期：——
• PADWA, ALBERT;KRUMPE, KEITH E.;GAREAU, YVES;CHIACCHIO, UGO, J. ORG. CHEM., 56,(1991) N, C. 2523-2530
  作者：PADWA, ALBERT、KRUMPE, KEITH E.、GAREAU, YVES、CHIACCHIO, UGO

  DOI：——

  日期：——