5-methyl-trans-2-(2,3-dihydro-1-oxo-1H-3-indenylidene)-2,3,4,5-tetrahydrofuran | 133446-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: 5-methyl-trans-2-(2,3-dihydro-1-oxo-1H-3-indenylidene)-2,3,4,5-tetrahydrofuran
• 英文别名: (3E)-3-(5-methyloxolan-2-ylidene)inden-1-one
• CAS: 133446-26-1
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: MBJBYRBUJJULBU-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  Methyl 2-<5-(2-methyl-1,3-dioxolan-2-yl)-1-butynyl>benzoate 在 Rh2[(+/-)-mandelate]4 sodium tetrahydroborate 、 potassium trimethylsilonate 、 4-甲基苯磺酸吡啶 、 氯甲酸甲酯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 41.0h， 生成 5-methyl-trans-2-(2,3-dihydro-1-oxo-1H-3-indenylidene)-2,3,4,5-tetrahydrofuran
  参考文献：
  名称：

  Rhodium(II)-catalyzed cyclization reactions of alkynyl-substituted .alpha.-diazo ketones

  摘要：

  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.

  DOI：

  10.1021/jo00007a047

文献信息

• 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：——
• 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：——