ethyl 5-hydroxy-2,4-dimethyl-5-(2-nitrophenyl)-2,3-pentadienoate

• 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 5-hydroxy-2,4-dimethyl-5-(2-nitrophenyl)-2,3-pentadienoate
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: UNIREDGVWZMIFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-hydroxy-2,4-dimethyl-5-(2-nitrophenyl)-2,3-pentadienoate 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以88%的产率得到ethyl 2,4-dimethyl-5-(2-nitrophenyl)-2,5-dihydro-2-furancarboxylate
  参考文献：
  名称：

  Guanidine-Catalyzed γ-Selective Morita–Baylis–Hillman Reactions on α,γ-Dialkyl-Allenoates: Access to Densely Substituted Heterocycles

  摘要：

  N-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) was discovered as an excellent catalyst for the Morita-Baylis-Hillman reaction for previously hard-to-activate ,-dialkyl allenoate substrates. The obtained densely substituted allenic alcohols, which are generally inaccessible with other Lewis base catalysts, could be further converted into 2,5-dihydrofuran and 2H-pyran-2-one heterocyclic structures with challenging substitution patterns.

  DOI：

  10.1055/s-0033-1339471
• 作为产物：
  描述：

  ethyl 2-methylpenta-2,3-dienoate 、 邻硝基苯甲醛 在 7-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以81%的产率得到ethyl 5-hydroxy-2,4-dimethyl-5-(2-nitrophenyl)-2,3-pentadienoate
  参考文献：
  名称：

  Guanidine-Catalyzed γ-Selective Morita–Baylis–Hillman Reactions on α,γ-Dialkyl-Allenoates: Access to Densely Substituted Heterocycles

  摘要：

  N-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) was discovered as an excellent catalyst for the Morita-Baylis-Hillman reaction for previously hard-to-activate ,-dialkyl allenoate substrates. The obtained densely substituted allenic alcohols, which are generally inaccessible with other Lewis base catalysts, could be further converted into 2,5-dihydrofuran and 2H-pyran-2-one heterocyclic structures with challenging substitution patterns.

  DOI：

  10.1055/s-0033-1339471

文献信息

• Guanidine-Catalyzed γ-Selective Morita–Baylis–Hillman Reactions on α,γ-Dialkyl-Allenoates: Access to Densely Substituted Heterocycles
  作者：Philipp Selig、Aleksej Turočkin、William Raven

  DOI：10.1055/s-0033-1339471

  日期：——

  N-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) was discovered as an excellent catalyst for the Morita-Baylis-Hillman reaction for previously hard-to-activate ,-dialkyl allenoate substrates. The obtained densely substituted allenic alcohols, which are generally inaccessible with other Lewis base catalysts, could be further converted into 2,5-dihydrofuran and 2H-pyran-2-one heterocyclic structures with challenging substitution patterns.