6-(2-Iodophenyl)-3,3,5,5-tetramethyldihydro-2H-pyran-2,4(3H)-dione

• 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: 6-(2-Iodophenyl)-3,3,5,5-tetramethyldihydro-2H-pyran-2,4(3H)-dione
• 英文别名: 6-(2-iodophenyl)-3,3,5,5-tetramethyloxane-2,4-dione
• 化学式: C₁₅H₁₇IO₃
• 分子量: 372.203
• InChiKey: YOWBFWKVCTVKTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘苯甲醛 、 ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate 在 锌 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 0.5h， 以70%的产率得到6-(2-Iodophenyl)-3,3,5,5-tetramethyldihydro-2H-pyran-2,4(3H)-dione
  参考文献：
  名称：

  摘要：

  Zinc enolates formed from ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate react under the conditions of one- of two-stage synthesis with aliphatic, unsaturated, or aromatic aldehydes to form 6-R-2,2,4,4-tetramethyl-2,3,5,6-tetrahydropyran-2,4-diones. Zinc enolates obtained from ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate, -hexanoate, and -2,2,5-trimethyl-3-oxohexanoate under the similar conditions react with aliphatic or aromatic aldehydes to give mainly 5-R-1-6-R-2-3,3-dimethyl-2,3,5,6-tetrahydropyran-2,4-diones as E or Z isomers or their mixtures. Zinc enolates generated from the ethyl 4-bromo-2,2-diethyl- or 2-benzyl-2-ethyl-3-oxobutanoates react with aromatic aldehydes to give ethyl 5-R-2-R-2-ethyl-3-oxo-4-pentenoates as E isomers.

  DOI：

  10.1023/a:1025600905960

文献信息

• ——
  作者：V. V. Shchepin、Yu. Kh. Sazhneva、D. N. Litvinov

  DOI：10.1023/a:1025600905960

  日期：——

  Zinc enolates formed from ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate react under the conditions of one- of two-stage synthesis with aliphatic, unsaturated, or aromatic aldehydes to form 6-R-2,2,4,4-tetramethyl-2,3,5,6-tetrahydropyran-2,4-diones. Zinc enolates obtained from ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate, -hexanoate, and -2,2,5-trimethyl-3-oxohexanoate under the similar conditions react with aliphatic or aromatic aldehydes to give mainly 5-R-1-6-R-2-3,3-dimethyl-2,3,5,6-tetrahydropyran-2,4-diones as E or Z isomers or their mixtures. Zinc enolates generated from the ethyl 4-bromo-2,2-diethyl- or 2-benzyl-2-ethyl-3-oxobutanoates react with aromatic aldehydes to give ethyl 5-R-2-R-2-ethyl-3-oxo-4-pentenoates as E isomers.