3-methyl-2-(5-oxohexyl)cyclopent-2-enone | 925217-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-2-(5-oxohexyl)cyclopent-2-enone
• 英文别名: 3-Methyl-2-(5-oxohexyl)cyclopent-2-en-1-one
• CAS: 925217-22-7
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: MRUFPZYUAFHKKA-UHFFFAOYSA-N

物化性质

• 沸点：
  338.0±31.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：

  3-methyl-2-(5-oxohexyl)cyclopent-2-enone 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到2-(5-hydroxyhexyl)-3-methylcyclopentanone
  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-ethylenedioxyhexyl)-2-cyclopenten-1-one 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 43.0h， 以69%的产率得到3-methyl-2-(5-oxohexyl)cyclopent-2-enone
  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

文献信息

• Palladium-catalyzed cross-coupling reaction of alkenyl bromides with potassium alkyltrifluoroborates
  作者：Gary A. Molander、Jungyeob Ham、Dave G. Seapy

  DOI：10.1016/j.tet.2006.10.088

  日期：2007.1

  The Suzuki-Miyaura-type cross-coupling reaction of potassium alkyltrifluoroborates with various alkenyl bromides in the presence of 10 mol % of PdCl(2)(dppf).CH(2)Cl(2) and 3.0 equiv of Cs(2)CO(3) in aqueous toluene at 80 degrees C provided the desired compounds in 49-95% yields. A variety of functional groups in the potassium alkyltrifluoroborates were tolerated under the basic conditions.

  在10摩尔％的PdCl（2）（dppf）.CH（2）Cl（2）和3.0当量的Cs（2）CO存在下，烷基三氟硼酸钾与各种烯基溴化物的Suzuki-Miyaura型交叉偶联反应（3）在80℃的甲苯水溶液中以49-95％的收率提供了所需的化合物。在碱性条件下可耐受烷基三氟硼酸钾中的各种官能团。