(3Z,5E)-4-hydroxy-8-methylnona-3,5,7-triene-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3Z,5E)-4-hydroxy-8-methylnona-3,5,7-triene-2-one
• 英文别名: (3Z,5E)-4-hydroxy-8-methyl-3,5,7-nonatrien-2-one；(3z,5e)-4-Hydroxy-8-methylnona-3,5,7-triene-2-one；(3Z,5E)-4-hydroxy-8-methylnona-3,5,7-trien-2-one
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: MMIQJWNHNFVCFI-JSRXJHBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-2,4-戊二酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.71h， 生成 (3Z,5E)-4-hydroxy-8-methylnona-3,5,7-triene-2-one
  参考文献：
  名称：

  An Efficient Separation Method for Enol Phosphate and Corresponding β-Ketophosphonate from Their Mixtures Under Aqueous Conditions

  摘要：

  Separation of a mixture beta-ketophosphonate 3 and their corresponding enol phosphate 4 is efficiently carried out in aqueous alkaline solutions. Enol phosphate 4 is first extracted with hexanes:dichloromethane (19:1). Acidification of the aqueous layer followed by extraction of the beta-ketophosphonate 3 with dichloromethane completes the separation. Thus, when 1-bromo-2,4-pentadione 1a reacted with triethyl phosphite to give diethyl (2,4-dioxopentyl)phosphonate 3a (Arbuzov-product) and the corresponding enol phosphate 4a (Perkow-product), separation of the two compounds was carried out using this method.

  DOI：

  10.1081/scc-120021033

文献信息

• Condensations of ?-Acetylacetonephosphonium Ylide (1-(Triphenylphosphoranylidene) pentane-2,4-dione) with Carbonyl Compounds
  作者：Cornelis M. Moorhoff

  DOI：10.1007/s00706-002-0548-x

  日期：2003.2.1

  pentane-2,4-dione. Dianion Wittig - and Michael Wittig condensations of the last mentioned phosphonium ylide with carbonyl compounds gave unsaturated 2,4-diketones which were almost totally enolised in deutero chloroform as 4-hydroxy-2-oxo-3,5-dienes (24–70% yields). These products closely resembled the type of compounds derived from similar condensations with alkyl 3-oxo-4-(triphenylphosphoranylidene)butanoate

  2,4-二氧戊基三苯基溴化with与碳酸氢钠水溶液在二氯甲烷中反应，以几乎定量的产率得到1-（三苯基正膦亚基）戊烷-2,4-二酮。最后提到的叶立德phospho叶立德与羰基化合物的Dianion Wittig 和 Michael Wittig 缩合反应生成不饱和的2,4-二酮，几乎完全在氘代氯仿中烯醇化为4-羟基-2-氧代-3,5-二烯（24-70％产量）。这些产物与3​​-氧代-4-（三苯基正膦亚基）丁酸酯的类似缩合反应衍生的化合物的类型非常相似。
• An Efficient Separation Method for Enol Phosphate and Corresponding β-Ketophosphonate from Their Mixtures Under Aqueous Conditions
  作者：Cornelis M. Moorhoff

  DOI：10.1081/scc-120021033

  日期：2003.7

  Separation of a mixture beta-ketophosphonate 3 and their corresponding enol phosphate 4 is efficiently carried out in aqueous alkaline solutions. Enol phosphate 4 is first extracted with hexanes:dichloromethane (19:1). Acidification of the aqueous layer followed by extraction of the beta-ketophosphonate 3 with dichloromethane completes the separation. Thus, when 1-bromo-2,4-pentadione 1a reacted with triethyl phosphite to give diethyl (2,4-dioxopentyl)phosphonate 3a (Arbuzov-product) and the corresponding enol phosphate 4a (Perkow-product), separation of the two compounds was carried out using this method.