3-methyldihydro-3,4-dibromo-2(3H)-furanone

• 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-methyldihydro-3,4-dibromo-2(3H)-furanone
• 英文别名: InChI=1/C5H6Br2O2/c1-5(7)3(6)2-9-4(5)8/h3H,2H2,1H；3,4-dibromo-3-methyloxolan-2-one
• 化学式: C₅H₆Br₂O₂
• 分子量: 257.909
• InChiKey: YKJURPJTZGVSML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  α-甲基-γ-丁内酯 在 溴 作用下， 以 四氯化碳 为溶剂， 生成 3-methyldihydro-3,4-dibromo-2(3H)-furanone
  参考文献：
  名称：

  Stereochemistry of alkyl 3-substituted 4-halotetrahydro-2-oxo-3-furancarboxylates: 2—1H and13C NMR spectra

  摘要：

  AbstractThe 1H NMR parameters of methyl 3‐substituted cis‐4‐halotetrahydro‐2‐oxo‐3‐furancarboxylates are reported, with assignments of the ring protons based on solvent‐induced changes in the vicinal trans coupling constants, 3J(H‐4, H‐5). Preferred conformations, ce with a pseudo‐equatorial halogen for the cis isomers and ta with a pseudo‐axial halogen for the trans isomers, have been suggested on comparison of the magnitudes of J(trans) and J(gem) in both series. The 3J(13CH3, H‐4) values measured for methyl cis‐4‐bromotetrahydro‐3‐methyl‐3‐furancarboxylate, methyl trans‐4‐bromotetrahydro‐3‐methyl‐3‐furancarboxylate and trans‐3,4‐dibromodihydro‐3‐methyl‐2(3H)‐furanone have confirmed the stereochemical assignments.

  DOI：

  10.1002/omr.1270210302

文献信息

• Stereochemistry of alkyl 3-substituted 4-halotetrahydro-2-oxo-3-furancarboxylates: 2—1H and13C NMR spectra
  作者：A. Gryff-Keller、W. Kołodziejek、J. Prejzner

  DOI：10.1002/omr.1270210302

  日期：1983.3

  AbstractThe 1H NMR parameters of methyl 3‐substituted cis‐4‐halotetrahydro‐2‐oxo‐3‐furancarboxylates are reported, with assignments of the ring protons based on solvent‐induced changes in the vicinal trans coupling constants, 3J(H‐4, H‐5). Preferred conformations, ce with a pseudo‐equatorial halogen for the cis isomers and ta with a pseudo‐axial halogen for the trans isomers, have been suggested on comparison of the magnitudes of J(trans) and J(gem) in both series. The 3J(13CH3, H‐4) values measured for methyl cis‐4‐bromotetrahydro‐3‐methyl‐3‐furancarboxylate, methyl trans‐4‐bromotetrahydro‐3‐methyl‐3‐furancarboxylate and trans‐3,4‐dibromodihydro‐3‐methyl‐2(3H)‐furanone have confirmed the stereochemical assignments.

表征谱图