4-Butyloct-3-enal | 920299-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Butyloct-3-enal
• CAS: 920299-37-2
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: SNOIDBZBAIINRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  255.5±9.0 °C(Predicted)
• 密度：
  0.838±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-壬酮 在 manganese(IV) oxide 、 disodium hydrogenphosphate 、 lithium aluminium tetrahydride 、 正丁基锂 、 六氟乙酰丙酮化铜的水合物 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 126.0h， 生成 4-Butyloct-3-enal
  参考文献：
  名称：

  Copper-Catalyzed Rearrangement of Vinyl Oxiranes

  摘要：

  A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.

  DOI：

  10.1021/ja067073o

文献信息

• Production of 2,5-Dihydrofurans and Analogous Compounds
  申请人：Njardarson Jon

  公开号：US20090131691A1

  公开（公告）日：2009-05-21

  Vinyl oxiranes are rearranged to 2,5-dihydrofuran using catalyst (III) or (IV). The 2,5-dihydrofuran can be reduced to tetrahydrofuran. 3,4-Epoxy-1-butene substrate is converted to 2,5-dihydrofuran which in turn is converted to tetrahydrofuran. Substrate for making 3-methyltetrahydrofuran is prepared from isoprene. Substrate for making 2-methyltetrahydrofuran is prepared from piperylene. Reactions analogous to that with vinyl oxiranes are carried out with vinyl thiiranes and vinyl aziridines.

  乙烯基环氧烷通过催化剂（III）或（IV）重排成2,5-二氢呋喃。2,5-二氢呋喃可以还原成四氢呋喃。3,4-环氧-1-丁烯底物被转化为2,5-二氢呋喃，然后转化为四氢呋喃。制备3-甲基四氢呋喃的底物来自异戊二烯。制备2-甲基四氢呋喃的底物来自戊二烯。与乙烯基环氧硫烷和乙烯基氮杂环丙烷类似的反应也可以进行。
• WO2007/108999
  申请人：——

  公开号：——

  公开（公告）日：——
• US8404872B2
  申请人：——

  公开号：US8404872B2

  公开（公告）日：2013-03-26
• Copper-Catalyzed Rearrangement of Vinyl Oxiranes
  作者：Lindsay A. Batory、Christine E. McInnis、Jon T. Njardarson

  DOI：10.1021/ja067073o

  日期：2006.12.1

  A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.