(E)-non-5-eno-9-lactone | 110189-59-8

• 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: (E)-non-5-eno-9-lactone
• 英文别名: (E)-non-5-en-9-olide；(6E)-3,4,5,8,9,10-hexahydro-2H-oxecin-2-one；(5E)-2,3,4,7,8,9-hexahydrooxecin-10-one
• CAS: 110189-59-8
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: ZMWLDAFJOZSOOT-OWOJBTEDSA-N

物化性质

• 沸点：
  284.7±29.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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 (E)-non-5-eno-9-lactone
  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

• Hypervalent Organoiodine-Promoted Oxidative Ring Expansions of Tributylstannyl Lactols. New and General Synthesis of Unsaturated Medium-Ring Lactones
  作者：Masahito Ochiai、Shigeru Iwaki、Tatsuzo Ukita、Yoshimitsu Nagao

  DOI：10.1246/cl.1987.133

  日期：1987.1.5

  A new ring expansion route to olefinic lactones was developed. Oxidative 1,4-fragmentation of tributylstannyl lactols utilizing (diacetoxyiodo)bezene under mild conditions gave unsaturated medium-ring lactones stereospecifically in good yields. The relative stereochemistry of tributylstannyl group of the lactols determines the double bond geometry of the lactones.

  开发了烯烃内酯的新扩环路线。在温和条件下利用（二乙酰氧基碘）苯对三丁基甲锡基内酯进行氧化 1,4-断裂，以良好的收率立体特异性地得到不饱和中环内酯。内酯的三丁基甲锡烷基的相对立体化学决定了内酯的双键几何结构。
• Efficient synthesis of functionalised ten-membered lactones via acid-catalysed intramolecular reactions of 5-(tetrahydro 2-furyl)pentanoic trifluoroacetic anhydride
  作者：David H. Grayson、Edwin D. Roycroft

  DOI：10.1039/c39930000269

  日期：——

  5-(Tetrahydro-2-furyl)pentanoic trifluoroacetic anhydride reacts in the presence of trifluoroacetic acid to yield 6-trifluoroacetoxy-9-nonanolide together with (E)-non-5-en-9-olide; treatment of the same mixed anhydride with titanium(IV) chloride gives 6-chloro-9-nonanolide, and its reaction with trifluoroacetic acid in the presence of sodium iodide leads to 6-iodo-9-nonanolide.

  5-（四氢-2-呋喃基）戊酸三氟乙酸酐在三氟乙酸存在下发生反应，生成 6-三氟乙酰氧基-9-壬醇内酯和 (E)-壬-5-烯-9-醇内酯；将相同的混合酸酐与氯化钛（IV）处理，可生成 6-氯-9-壬醇内酯，其与三氟乙酸在碘化钠存在下发生反应，可生成 6-碘-9-壬醇内酯。
• 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.
• OCHIAI MASAHITO; IWAKI SHIGERU; UKITA TATSUZO; NAGAO YOSHIMITSU, CHEM. LETT.,(1987) N 1, 133-136
  作者：OCHIAI MASAHITO、 IWAKI SHIGERU、 UKITA TATSUZO、 NAGAO YOSHIMITSU

  DOI：——

  日期：——
• ——
  作者：Yu. N. Ogibin、A. O. Terent"ev、V. P. Ananikov、G. I. Nikishin

  DOI：10.1023/a:1015009603719

  日期：——

  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.

表征谱图