(+/-)-4-exo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (+/-)-4-exo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one
• 英文别名: 3a,4-dihydro-3-hydroxy-3H-cyclopenta[b]furan-2(6aH)-one；(3R,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one；3-hydroxy-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one；Rel-(3R,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one；(3R,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: LOTRXPYWDQSASJ-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (+/-)-4-exo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以93%的产率得到(1R*,5S*)-5-[(1R*)-1,2-dihydroxyethyl]-cyclopent-2-en-1-ol
  参考文献：
  名称：

  A Facile Synthesis of cis-9-[4-(1,2-Dihydroxyethyl)-cyclopent-2-enyl]guanine and Its Derivative

  摘要：

  The synthesis of carbocyclic nucleosides, cis-9-[4-(1,2-dihydroxyethyl)-cyclopent-2-enyl]guanine (3) and cis-2-amino-6-cyclopropylamino-9-[4-(1,2-dihydroxyethyl)-cyclopent-2- enyl]purine (4), was achieved from cyclopentadiene (5) in five and six steps, respectively. This route involves a hetero Diels-Alder reaction and a Pd(0)-catalyzed coupling reaction.

  DOI：

  10.1080/15257770008035034
• 作为产物：
  描述：

  环戊二烯 、 乙醛酸 在 bismuth(lll) trifluoromethanesulfonate 、 水 作用下， 反应 2.0h， 生成 (3S,3aR,6aR)-3a,4-dihydro-3-hydroxy-3H-cyclopenta[b]furan-2(6aH)-one 、 (+/-)-4-exo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one
  参考文献：
  名称：

  Enhancement of Dienophilic and Enophilic Reactivity of the Glyoxylic Acid by Bismuth(III) Triflate in the Presence of Water

  摘要：

  三氟甲烷磺酸铋(III)（1）在水的存在下，能够高效催化羟基乙酸与经典二烯或取代烯烃之间的羰基-达尔斯-阿尔德反应或羰基-烯反应。

  DOI：

  10.1055/s-1998-1869

文献信息

• Enhancement of Dienophilic and Enophilic Reactivity of the Glyoxylic Acid by Bismuth(III) Triflate in the Presence of Water
  作者：H. Laurent-Robert、C. Le Roux、J. Dubac

  DOI：10.1055/s-1998-1869

  日期：1998.10

  Bismuth(III) trifluoromethanesulfonate (1) is found to efficiently catalyze carbonyl-Diels-Alder or carbonyl-ene reactions between glyoxylic acid and classical dienes or substituted olefins, in the presence of water.

  三氟甲烷磺酸铋(III)（1）在水的存在下，能够高效催化羟基乙酸与经典二烯或取代烯烃之间的羰基-达尔斯-阿尔德反应或羰基-烯反应。
• Conversion of (–)-4-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one into the anti-HIV agent carbovir
  作者：Rosemary A. MacKeith、Ray McCague、Horacio F. Olivo、Christopher F. Palmer、Stanley M. Roberts

  DOI：10.1039/p19930000313

  日期：——

  The lactone (±)-1 was resolved using Pseudomonas fluorescens lipase and vinyl acetate; the ester (–)-3 obtained by this process was subsequently converted into the anti-HIV agent carbovir (–)-9.

  使用荧光假单胞菌脂肪酶和乙酸乙烯酯拆分内酯（±）-1。随后将通过此方法获得的酯（–）- 3转化为抗HIV药剂carbovir（–）- 9。
• Formation of bromohydrins and epoxides from 4-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one and 9-hydroxy-7-oxabicyclo[4.3.0] non-4-en-8-one
  作者：Antonio Garofalo、Michael B. Hursthouse、K. M. Abdul Malik、Horacio F. Olivo、Stanley M. Roberts、Vladimir Sik

  DOI：10.1039/p19940001311

  日期：——

  The hydroxy lactone 1 and the silylated derivative 8 react selectively with HOBr to give access to polyfunctional bicyclic systems such as the bromo ester 10. The lactone 3 or the corresponding derivative 20 react less selectively to give mixtures of compounds 16, 17, 18, 19, 21, 22. The hydroxybicyclo[4.3.0]nonenones 2 and 4 behave in a similar fashion to the lactone 3, reacting non-selectively with

  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。
• Kinetic Resolution of Racemic 2-Hydroxy-γ-butyrolactones by Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst
  作者：Kenya Nakata、Kouya Gotoh、Keisuke Ono、Kengo Futami、Isamu Shiina

  DOI：10.1021/ol303453j

  日期：2013.3.15

  Various optically active 2-hydroxy-γ-butyrolactone derivatives are produced via the kinetic resolution of racemic 2-hydroxy-γ-butyrolactones with diphenylacetic acid using pivalic anhydride and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst. Importantly, the substrate scope of this novel protocol is fairly broad (12 examples, s-value; up to over 1000). In addition, we succeeded in

  使用新戊酸酐和（R）-苯并四咪唑（（R）-BTM），手性酰基-转移催化剂。重要的是，该新颖方案的底物范围相当广泛（12个例子，s值；最大超过1000）。此外，我们通过理论计算成功地揭示了提供高对映选择性的反应机理，并阐述了2-羟基内酯在C-3位置的取代基效应。
• A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters
  作者：Hao Chen、Srinivas Nagabandi、Steven Smith、Jonathan M. Goodman、Erika Plettner

  DOI：10.1016/j.tetasy.2009.02.007

  日期：2009.3

  The (+/-)-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol 1 was prepared in a one-pot procedure, and was resolved using lipase AK and vinyl acetate with high ee. This provides a readily available chiral synthon for the synthesis of a wide variety of biologically interesting molecules. Further, the absolute configuration of diol 1 was confirmed directly by the Mosher ester method. (c) 2009 Elsevier Ltd. All rights reserved.