diethyl (1E,4E)-1-ethoxy-3-hydroxy-5-methyl-1,4-hexadien-2-ylphosphonate | 286962-05-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl (1E,4E)-1-ethoxy-3-hydroxy-5-methyl-1,4-hexadien-2-ylphosphonate
• 英文别名: (1E)-2-diethoxyphosphoryl-1-ethoxy-5-methylhexa-1,4-dien-3-ol
• CAS: 286962-05-8
• 化学式: C₁₃H₂₅O₅P
• 分子量: 292.312
• InChiKey: FVGKGGHSQUEHPP-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (1E,4E)-1-ethoxy-3-hydroxy-5-methyl-1,4-hexadien-2-ylphosphonate 在 palladium on activated charcoal 三氟乙酸 、 氢气 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 18.0h， 以67%的产率得到diethyl 3,4-dihydro-2,2-dimethyl-2H-pyran-5-ylphosphonate
  参考文献：
  名称：

  Synthesis and Synthetic Application of α-Formylvinylphosphonates. Facile Synthesis of Phosphono-Substituted Heterocyclic Compounds

  摘要：

  The beta-ethoxy-alpha-phosphonovinyl anion, generated from beta-(ethoxy)vinylphosphonate 1 and LDA, reacted with aldehydes and ketones or phenyl isocyanate to give the corresponding allylic alcohols 2a-m or 1,3-diphenyl-5-phosphonouracil 4 in good or moderate yields. Treatment of the alcohols 2a-d,g,h,j with trifluoroacetic acid led to alpha-formylvinylphosphonates 5a-d,g,h,j in excellent yields. Synthetic application of the alpha-formylvinylphosphonates 5a-d,g,h to phosphono-substituted heterocyclic compounds was studied.

  DOI：

  10.1021/jo000149t
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 (E)-Diethyl 2-ethoxyethenylphosphonate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以96%的产率得到diethyl (1E,4E)-1-ethoxy-3-hydroxy-5-methyl-1,4-hexadien-2-ylphosphonate
  参考文献：
  名称：

  Synthesis and Synthetic Application of α-Formylvinylphosphonates. Facile Synthesis of Phosphono-Substituted Heterocyclic Compounds

  摘要：

  The beta-ethoxy-alpha-phosphonovinyl anion, generated from beta-(ethoxy)vinylphosphonate 1 and LDA, reacted with aldehydes and ketones or phenyl isocyanate to give the corresponding allylic alcohols 2a-m or 1,3-diphenyl-5-phosphonouracil 4 in good or moderate yields. Treatment of the alcohols 2a-d,g,h,j with trifluoroacetic acid led to alpha-formylvinylphosphonates 5a-d,g,h,j in excellent yields. Synthetic application of the alpha-formylvinylphosphonates 5a-d,g,h to phosphono-substituted heterocyclic compounds was studied.

  DOI：

  10.1021/jo000149t

文献信息

• Synthesis and Synthetic Application of α-Formylvinylphosphonates. Facile Synthesis of Phosphono-Substituted Heterocyclic Compounds
  作者：Ryoji Kouno、Terunobu Tsubota、Tatsuo Okauchi、Toru Minami

  DOI：10.1021/jo000149t

  日期：2000.7.1

  The beta-ethoxy-alpha-phosphonovinyl anion, generated from beta-(ethoxy)vinylphosphonate 1 and LDA, reacted with aldehydes and ketones or phenyl isocyanate to give the corresponding allylic alcohols 2a-m or 1,3-diphenyl-5-phosphonouracil 4 in good or moderate yields. Treatment of the alcohols 2a-d,g,h,j with trifluoroacetic acid led to alpha-formylvinylphosphonates 5a-d,g,h,j in excellent yields. Synthetic application of the alpha-formylvinylphosphonates 5a-d,g,h to phosphono-substituted heterocyclic compounds was studied.