trans-1-oxacyclodec-7-ene-2-one

• 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: trans-1-oxacyclodec-7-ene-2-one
• 英文别名: (E)-non-6-eno-9-lactone；(7E)-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one；(4E)-2,3,6,7,8,9-hexahydrooxecin-10-one
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: ZRPGMCAJIZEOIN-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4,5,6,7,8-hexahydro-2H-chromene 在 copper diacetate 、 硫酸 、 双氧水 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 生成 trans-1-oxacyclodec-7-ene-2-one
  参考文献：
  名称：

  摘要：

  Hydroperoxidation of C=C-bridged 2-oxabicycloalkenes in which the five- or six-membered oxacycle is fused with the five-, six-, or twelve-membered hydrocarbon ring was studied. The Cu(OAc)(2)-catalyzed decomposition of the resulting hydroperoxides afforded nine-, ten-, or fifteen-membered trans-alkenolides, respectively. The latter compounds were obtained as pairs of regioisomers, with the isomers in which the double bond is more remote from the ether oxygen atom predominating.

  DOI：

  10.1023/a:1015009603719

文献信息

• A highly stereoselective route to medium-ring-sized trans-alkenolides via oxidative fragmentation of bicyclic oxycyclopropane precursors: application to the synthesis of (+)-recifeiolide
  作者：Dzmitry M. Zubrytski、Dzmitry G. Kananovich、Oleg G. Kulinkovich

  DOI：10.1016/j.tet.2014.03.032

  日期：2014.5

  A new approach to the synthesis of medium-ring-sized trans-alkenolides, based on the oxidative fragmentation of a three-carbon ring in hydroxyalkyl substituted bicyclo[n.1.0]alkan-1-ols readily available from 2-alkylidenecycloalkanones, is described. This methodology was applied to the six-step transformation of cyclooctanone to the natural 12-membered trans-alkenolide antibiotic (+)-recifeiolide.

  描述了一种新的合成中环大小反式链烯内酯的方法，该方法基于三碳环在羟烷基取代的双环[ n .1.0]烷-1-醇中的三碳环的氧化裂解作用，二环[ n .1.0]烷-1-醇可从2-亚烷基环烷酮中轻松获得。 。该方法学适用于将环辛酮经六步转化为天然的12元反式-链烯内酯抗生素（+）-recifeiolide的步骤。
• Alkoxy radical accelerated β-fragmentation of alcohols and lactols
  作者：James H Rigby、Anne Payen、Namal Warshakoon

  DOI：10.1016/s0040-4039(01)00121-6

  日期：2001.3

  Treatment of alcohols and lactols with Pb(OAc)(4)/Cu(OAc)(2) in refluxing benzene provides the corresponding delta -unsaturated carbonyl products. (C) 2001 Elsevier Science Ltd. All rights reserved.

表征谱图