9-endo-hydroxy-7-oxabicyclo<4.3.0>non-4-en-8-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 9-endo-hydroxy-7-oxabicyclo<4.3.0>non-4-en-8-one
• 英文别名: endo-9-hydroxy-7-oxabicyclo<4.3.0>non-4-en-8-one；3,3a,4,5-tetrahydro-3-hydroxybenzofuran-2(7aH)-one；(3S,3aR,7aR)-3-hydroxy-3a,4,5,7a-tetrahydro-3H-1-benzofuran-2-one
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: CVSZHDPJIGWVDS-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-endo-hydroxy-7-oxabicyclo<4.3.0>non-4-en-8-one 在 4-二甲氨基吡啶 、 抗氧剂300 、 偶氮二异丁腈 、 氢碘酸 、 三正丁基氢锡 、 间氯过氧苯甲酸 作用下， 以 吡啶 、 1,2-二氯乙烷 、 丙酮 、 苯 为溶剂， 反应 5.0h， 生成 5-exo,9-endo-diacetoxy-7-oxabicyclo<4.3.0>nonan-8-one
  参考文献：
  名称：

  由4-羟基-2-氧杂双环[3.3.0] oct-7-en-3-one和9-羟基-7-氧杂双环[4.3.0] non-4-en-8-one形成溴代醇和环氧化物

  摘要：

  羟基内酯1和甲硅烷基化衍生物8与HOBr选择性反应，可进入多官能双环系统，如溴酸酯10。内酯3或相应的衍生物20反应更少选择性，得到的化合物的混合物16，17，18，19，21，22。羟基双环[4.3.0]壬烯酮2和4的行为与内酯3相似，与HOBr和m发生非选择性反应氯过苯甲酸，以产生化合物双环取代的高度过多23 - 31，33 - 39，41和42。对于四种化合物，二乙酸酯25和37以及环氧化物26和27，获得了X射线晶体结构。

  DOI：

  10.1039/p19940001311
• 作为产物：
  描述：

  (-)-endo-(1R,6R,9S)-9-acetoxy-7-oxabicyclo<4.3.0>non-4-en-8-one 在 sodium hydroxide 、 phosphate buffer pH 7.0 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以73.2%的产率得到9-endo-hydroxy-7-oxabicyclo<4.3.0>non-4-en-8-one
  参考文献：
  名称：

  Hibbs, David E.; Hursthouse, Michael B.; Knutsen, Lars J. S., Acta Chemica Scandinavica, 1995, vol. 49, # 2, p. 122 - 127

  摘要：

  DOI：

文献信息

• Solvent effects in asymmetric hetero Diels-Alder and ene reactions
  作者：Mogens Johannsen、Karl Anker Jørgensen

  DOI：10.1016/0040-4020(96)00254-2

  日期：1996.5

  The use of polar solvents such as nitromethane or 2-nitropropane leads to a significant improvement of the catalytic properties of a cationic copper-Lewis acid in the hetero Diels-Alder reaction of alkyl glyoxylates with dienes. The scope of a newly developed copper(II)-bisoxazoline catalyst for the hetero Diels-Alder reaction is demonstrated by the reaction of different dienes with alkyl glyoxylates

  在乙醛酸烷基酯与二烯的杂Diels-Alder反应中，使用极性溶剂（例如硝基甲烷或2-硝基丙烷）可显着改善阳离子铜-路易斯酸的催化性能。不同二烯与乙醛酸烷基酯在硝基烷溶剂中的反应，以及高对映体过量的杂Diels-Alder加合物的形成，证明了新开发的杂Diels-Alder反应铜（II）-双恶唑啉催化剂的范围。主要产品。该反应的合成应用以倍半萜内酯的高度有趣的合成子的改进合成为例。
• Practical enantiodivergent syntheses of both enantiomers of carbovir, 1592U89 and six-membered ring analogues
  作者：Horacio F. Olivo、Jiaxin Yu

  DOI：10.1039/a708261d

  日期：——

  The hydroxylactones 4a–b (both available in optically pure form from biocatalytic processes) have been used in the preparation of carbovir, 1592U89, and their six-membered ring analogues.

  羟基内酯 4a-b（均可通过生物催化过程获得光学纯品）已被用于制备卡巴韦、1592U89 及其六元环类似物。
• Asymmetric hetero Diels-Alder reactions and ene reactions catalyzed by chiral copper(II) complexes
  作者：Mogens Johannsen、Karl Anker Joergensen

  DOI：10.1021/jo00123a007

  日期：1995.9

  A new copper(II) bisoxazoline-catalyzed reaction of glyoxylate esters with dienes leading to the hetero Diet-Alder product and the ene product in high yield and with a high enantiomeric excess (ee) has been developed. The hetero Diels-Alder product:ene product ratio is in the range 1:0.6 to 1:1.8 and is dependent on both the chiral ligand attached to the metal, the glyoxylate ester, and the reaction temperature. The scope of the copper(II) bisoxazoline-catalyzed reaction of glyoxylate esters with dienes is demonstrated by the reaction of a variety of different dienes with ethyl and isopropyl glyoxylate, and it is shown that a simple substrate such as 1,3-butadiene reacts to give the hetero Diels-Alder product in 55% yield with an ee of 87%. Furthermore, the synthetic application of the reaction is demonstrated by the synthesis of a highly interesting synthon for sesquiterpene lactones in high yield and diastereoselectivity, and with a very high ee from 1,3-cyclohexadiene and ethyl glyoxylate using a copper(II) bisoxazoline as the catalyst. A mechanism for the hetero Diels-Alder reaction, which accounts for the enantioselectivity in the reactions, is proposed.
• Hetero Diels-Alder reaction in water. Synthesis of α-hydroxy-γ-lactones
  作者：André Lubineau、Jacques Augé、Nadège Lubin

  DOI：10.1016/0040-4039(91)80525-b

  日期：1991.12

  The hetero Diels-Alder reaction of cyclopentadiene or cyclohexadiene with aqueous solution of glyoxylic acid produces alpha-hydroxy-gamma-lactones arising from the rearrangement of the cycloadducts.
• Aqueous hetero Diels-Alder reactions: The carbonyl case.
  作者：A. Lubineau、J. Augé、E. Grand、N. Lubin

  DOI：10.1016/s0040-4020(01)81759-2

  日期：1994.8

  Commercially available aqueous solution of glyoxylic acid, pyruvaldehyde and glyoxal were shown to react with cyclic or non-cyclic dienes to give the corresponding cycloadducts and/or alpha-hydroxy gamma-lactones. Activated ketone (Pyruvic acid) was shown to react as well in the same conditions.