5-(2-methyl-6-oxocyclohex-1-enyl)pentanal | 1093945-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2-methyl-6-oxocyclohex-1-enyl)pentanal
• 英文别名: 5-(2-Methyl-6-oxocyclohexen-1-yl)pentanal
• CAS: 1093945-17-5
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: QPKHWYOKFLHHGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-methyl-6-oxocyclohex-1-enyl)pentanal 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-(1S,2R,7S)-2-hydroxy-1-methylbicyclo[5.4.0]undecan-8-one 、 (+/-)-(1S,2S,7S)-2-hydroxy-1-methylbicyclo[5.4.0]undecan-8-one 、 (+/-)-(1S,2R,7R)-2-hydroxy-1-methylbicyclo[5.4.0]undecan-8-one 、 (+/-)-(1S,2S,7R)-2-hydroxy-1-methylbicyclo[5.4.0]undecan-8-one
  参考文献：
  名称：

  Preparation of seven- and eight-membered rings by carbon–carbon bond formation induced by samarium diiodide: 7-endo- and 8-endo-trig type cyclization to bicyclo[5.3.0]decanolone, bicyclo[5.4.0]undecanolone, and bicyclo[6.4.0]dodecanolone

  摘要：

  Compounds with an enone-aldehyde/ketone were treated with Sml(2) to form the bicyclic ketols, bicyclo[5.3.0]decanolones, and bicyclo[5.4.0]undecanolones, in different ratios depending on the reaction conditions (with or without different amounts of additives, low temperature or rt). The tendency to form seven-membered rings was different from that of six-membered rings and the mechanisms for these reactions are proposed. Cyclization to an eight-membered ring was attempted realizing in the yield of 26%. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.073
• 作为产物：
  描述：

  3-methyl-2-(5-hydroxypentyl)cyclohex-2-enone 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以84%的产率得到5-(2-methyl-6-oxocyclohex-1-enyl)pentanal
  参考文献：
  名称：

  Preparation of seven- and eight-membered rings by carbon–carbon bond formation induced by samarium diiodide: 7-endo- and 8-endo-trig type cyclization to bicyclo[5.3.0]decanolone, bicyclo[5.4.0]undecanolone, and bicyclo[6.4.0]dodecanolone

  摘要：

  Compounds with an enone-aldehyde/ketone were treated with Sml(2) to form the bicyclic ketols, bicyclo[5.3.0]decanolones, and bicyclo[5.4.0]undecanolones, in different ratios depending on the reaction conditions (with or without different amounts of additives, low temperature or rt). The tendency to form seven-membered rings was different from that of six-membered rings and the mechanisms for these reactions are proposed. Cyclization to an eight-membered ring was attempted realizing in the yield of 26%. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.073