diethyl (E)-1-formyl-2-phenylvinylphosphonate | 286962-09-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: diethyl (E)-1-formyl-2-phenylvinylphosphonate
• 英文别名: (E)-2-diethoxyphosphoryl-3-phenylprop-2-enal
• CAS: 286962-09-2
• 化学式: C₁₃H₁₇O₄P
• 分子量: 268.249
• InChiKey: XFXDJDFKVOZIHH-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (E)-1-formyl-2-phenylvinylphosphonate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 diethyl 4,5-dihydro-5-phenyl-1H-pyrazol-4-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：

  (E)-Diethyl 2-ethoxyethenylphosphonate 在 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 diethyl (E)-1-formyl-2-phenylvinylphosphonate
  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.