ethyl (2E,4E)-3-methyl-5-phenyl-2-propan-2-ylpenta-2,4-dienoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (2E,4E)-3-methyl-5-phenyl-2-propan-2-ylpenta-2,4-dienoate
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: OPHSXYIJMXZKOW-SIDAKMONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  triethyl 3-methyl-4-phosphonocrotonate 在 氢氧化钾 、 18-冠醚-6 、 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 1.0h， 生成 ethyl (2E,4E)-3-methyl-5-phenyl-2-propan-2-ylpenta-2,4-dienoate
  参考文献：
  名称：

  Regioselectivity in the C-alkylation of triethyl 3-methyl-4-phosphonobut-2-enoate

  摘要：

  The reaction of triethyl 3-methyl-4-phosphonobut-2-enoate (1) with three alkyl halides AlkX (Alk = Pr-i, Me2CHCH2CH2, and c-C5H9; X = Br, I) in the system KOH(solid)-DMF-(Bu4NBr)-N-n at similar to 20 degrees C gives exclusively products of alkylation at C(2) with Delta(2) and/or Delta(3) position of the double bond. Under the same conditions, the reaction of 1 with MeI gives a mixture of products with different substitution pat erns. Only the use of an ion pair extraction technique affords 2-methyl-Delta(2)-products selectively, albeit in rather moderate yields. The Horner-Emmons olefination of PhCHO with the resulting phosphonates gives ethyl 2-alkyl-3-methyl-5-phenylpenta-2,4-dienoates in high yields.

  DOI：

  10.1007/bf02495128

文献信息

• Regioselectivity in the C-alkylation of triethyl 3-methyl-4-phosphonobut-2-enoate
  作者：G. V. Kryshtal'、G. M. Zhdankina、E. P. Serebryakov

  DOI：10.1007/bf02495128

  日期：1997.10

  The reaction of triethyl 3-methyl-4-phosphonobut-2-enoate (1) with three alkyl halides AlkX (Alk = Pr-i, Me2CHCH2CH2, and c-C5H9; X = Br, I) in the system KOH(solid)-DMF-(Bu4NBr)-N-n at similar to 20 degrees C gives exclusively products of alkylation at C(2) with Delta(2) and/or Delta(3) position of the double bond. Under the same conditions, the reaction of 1 with MeI gives a mixture of products with different substitution pat erns. Only the use of an ion pair extraction technique affords 2-methyl-Delta(2)-products selectively, albeit in rather moderate yields. The Horner-Emmons olefination of PhCHO with the resulting phosphonates gives ethyl 2-alkyl-3-methyl-5-phenylpenta-2,4-dienoates in high yields.