3-bromo-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-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: 3-bromo-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one
• 英文别名: endo-3-Bromo-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one；(3S,3aS,6aR)-3-bromo-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one
• 化学式: C₇H₇BrO₂
• 分子量: 203.035
• InChiKey: GSYTWSCJCDFRJG-JKUQZMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium diethylmalonate 、 3-bromo-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 在 四(三苯基膦)钯 作用下， 生成
  参考文献：
  名称：

  Palladium-Catalyzed Substitution of Unsaturated Lactones. Application to the Synthesis of Carbocyclic Polyoxins and Nikkomycins

  摘要：

  DOI：

  10.1021/jo952187w
• 作为产物：
  描述：

  3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 在 N-溴代丁二酰亚胺(NBS) 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-bromo-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  氨基苯甲酸雌三醇类似物的合成

  摘要：

  卡巴类似物1，14，15和16 Strigol的合成中的乙烯基醚的氧被亚甲基代替。化合物1是通过基团2与醛3的维蒂希反应制备的。使用Tanaka等人的方法，分别通过醛20与内酯17、18和19的反应来制备该方法失败的化合物14、15和16。35,36或膦酸酯32和33，在Wittig-Horner反应中。随后氧化消除硫醚部分，得到所需产物。

  DOI：

  10.1002/recl.19941130103

文献信息

• 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.
• Scope and Limitations in Palladium-Catalyzed Substitution Reactions of Unsaturated Fused Lactones
  作者：Varinder K. Aggarwal、Nuno Monteiro、Gary J. Tarver、Ray McCague

  DOI：10.1021/jo962106b

  日期：1997.7.1

  The palladium-catalyzed nucleophilic substitution of C-4-substituted 2-oxabicyclo[3.3.0]oct-7-en-3-ones (unsaturated, fused lactones) have been studied particularly in relation to how electronic and steric factors influenced the rate and efficiency of substitution reactions. Thus, a range of a-substituted lactones were prepared (X = H, Me, OH, OAc, Br, N-3, NHCBZ) and subjected to palladium-catalyzed substitution reaction with diethyl sodiomalonate, and it was found that reaction rates increased with increasing electron-withdrawing ability of the substituent and that there was a strong correlation between rate and pK(a) of the corresponding substituted acetic acids (XCH2-CO2H). The only exception to the correlation was with X = OH, in which case the endo isomer reacted considerably faster than expected and the exo isomer reacted much slower than expected. It was also found that the rates of reaction of the endo isomers were greater than the exo isomers. The increased rates have been accounted for by a shift in equilibrium between the lactone and the pi-allyl palladium intermediate toward the latter species due to the increased stability of the carboxylate (electronic effects) or relief of steric hindrance in the starting lactone. The scope and limitations of the palladium-catalyzed substitution reaction were studied by reacting a range of lactones with a range of nucleophiles. Lactones with unactivated leaving groups such as 2 (X = H) coupled efficiently with good nucleophiles such as malonate but only poorly with less reactive nucleophiles such as azide. Lactones with activated leaving groups such as 4a (X = OH) coupled efficiently with a broad range of nucleophiles.
• Palladium-Catalyzed Substitution of Unsaturated Lactones. Application to the Synthesis of Carbocyclic Polyoxins and Nikkomycins
  作者：Varinder K. Aggarwal、Nuno Monteiro、Gary J. Tarver、Steven D. Lindell

  DOI：10.1021/jo952187w

  日期：1996.1.1
• Synthesis of carba-strigol analogues
  作者：M. A. Kishimba、B. Zwanenburg

  DOI：10.1002/recl.19941130103

  日期：——

  Carba analogues 1, 14, 15 and 16 of Strigol were synthesised in which the vinyl ether oxygen is replaced by methylene. Compound 1 was prepared by the Wittig reaction of ylid 2 with aldehyde 3. Compounds 14, 15 and 16, for which this approach failed, were prepared by reaction of aldehyde 20 with lactones 17, 18 and 19, respectively, using the method of Tanaka et al.35,36, or with phosphonates 32 and

  卡巴类似物1，14，15和16 Strigol的合成中的乙烯基醚的氧被亚甲基代替。化合物1是通过基团2与醛3的维蒂希反应制备的。使用Tanaka等人的方法，分别通过醛20与内酯17、18和19的反应来制备该方法失败的化合物14、15和16。35,36或膦酸酯32和33，在Wittig-Horner反应中。随后氧化消除硫醚部分，得到所需产物。