ethyl 2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-oxo-6-carboxilate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: ethyl 2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-oxo-6-carboxilate
• 英文别名: ethyl (1R,2S,4R,5R)-2,4-dimethyl-3-oxo-8-oxabicyclo[3.2.1]oct-6-ene-6-carboxylate
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: CVDFVQREOANIGU-RHXIMWGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-糠酸 在 氯化亚砜 、 铜 、 sodium iodide 、 锌 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 ethyl 2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-oxo-6-carboxilate
  参考文献：
  名称：

  [4+3] Cycloaddition of C-3 substituted furans. Stereoselectivity induced by coordination effects

  摘要：

  Several C-3 substituted furans with chelating groups have been reacted with 2,3-dibromo-3-pentanone in the presence of a reducing metal, resulting in the formation of [4+3]-cycloadducts with complete cis-trans and endo-exo diastereoselectivity and in excellent yield. A certain variability of the conversion and reaction yield could be observed, when changing the reaction conditions, but in all cases the stereoselectivity was complete, compared to that of C-3 substituted furans with non-chelating groups. Also, a general method of assignment of stereochemistry of cycloadducts has been established by NMR, considering diagnostic patterns of signals with different multiplicity and chemical shifts depending on the stereochemistry of diastereomeric cycloadducts. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.070

文献信息

• [4+3] Cycloaddition of C-3 substituted furans. Stereoselectivity induced by coordination effects
  作者：Ángel M. Montaña、Pedro M. Grima、María Castellví、Consuelo Batalla、Mercè Font-Bardia

  DOI：10.1016/j.tet.2012.09.070

  日期：2012.12

  Several C-3 substituted furans with chelating groups have been reacted with 2,3-dibromo-3-pentanone in the presence of a reducing metal, resulting in the formation of [4+3]-cycloadducts with complete cis-trans and endo-exo diastereoselectivity and in excellent yield. A certain variability of the conversion and reaction yield could be observed, when changing the reaction conditions, but in all cases the stereoselectivity was complete, compared to that of C-3 substituted furans with non-chelating groups. Also, a general method of assignment of stereochemistry of cycloadducts has been established by NMR, considering diagnostic patterns of signals with different multiplicity and chemical shifts depending on the stereochemistry of diastereomeric cycloadducts. (C) 2012 Elsevier Ltd. All rights reserved.