2-hydroxy-1-methylbicyclo[6.4.0]dodecan-9-one | 1093945-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-1-methylbicyclo[6.4.0]dodecan-9-one
• CAS: 1093945-39-1
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: XLQNPLFAYLOFBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  6-(2-methyl-6-oxocyclohex-1-enyl)hexanal 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以11%的产率得到2-hydroxy-1-methylbicyclo[6.4.0]dodecan-9-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