isoferulaldehyde | 192120-46-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: isoferulaldehyde
• 英文别名: 3-(4-methoxy-3-methylphenyl)prop-2-enal
• CAS: 192120-46-0
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: IJNZQGWGATTXNO-UHFFFAOYSA-N

物化性质

• 沸点：
  315.8±27.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  isoferulaldehyde 、 4-(diethoxyphosphoryl)-but-2-enoic acid ethyl ester 在 potassium tert-butylate 、 氧气 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以65%的产率得到ethyl 4-hydroxy-4'-methoxy-3'-methylbiphenyl-2-carboxylate
  参考文献：
  名称：

  Oxygenative and Dehydrogenative [3 + 3] Benzannulation Reactions of α,β-Unsaturated Aldehydes and γ-Phosphonyl Crotonates Mediated by Air: Regioselective Synthesis of 4-Hydroxybiaryl-2-carboxylates

  摘要：

  Regioselective synthesis of 4-hydroxybiphenyl-2-carboxylates via the base-mediated oxygenative [3 + 3] benzannulation reaction of alpha,beta-unsaturated aldehydes and gamma-phosphonyl crotonates is reported. A hydroxyl group is installed in the final product on the originally phosphorus-bound carbon via a novel oxygenative and dehydrogenative transformation. The reaction proceeds rapidly in an open flask, uses atmospheric oxygen as an oxidant, and affords good yields of substituted biaryl phenols.

  DOI：

  10.1021/acs.orglett.6b00016
• 作为产物：
  描述：

  4-甲氧基-3-甲基苯甲醛 、 甲酰甲撑基三苯基磷 以 甲苯 为溶剂， 生成 isoferulaldehyde
  参考文献：
  名称：

  Oxygenative and Dehydrogenative [3 + 3] Benzannulation Reactions of α,β-Unsaturated Aldehydes and γ-Phosphonyl Crotonates Mediated by Air: Regioselective Synthesis of 4-Hydroxybiaryl-2-carboxylates

  摘要：

  Regioselective synthesis of 4-hydroxybiphenyl-2-carboxylates via the base-mediated oxygenative [3 + 3] benzannulation reaction of alpha,beta-unsaturated aldehydes and gamma-phosphonyl crotonates is reported. A hydroxyl group is installed in the final product on the originally phosphorus-bound carbon via a novel oxygenative and dehydrogenative transformation. The reaction proceeds rapidly in an open flask, uses atmospheric oxygen as an oxidant, and affords good yields of substituted biaryl phenols.

  DOI：

  10.1021/acs.orglett.6b00016

文献信息

• Oxygenative and Dehydrogenative [3 + 3] Benzannulation Reactions of α,β-Unsaturated Aldehydes and γ-Phosphonyl Crotonates Mediated by Air: Regioselective Synthesis of 4-Hydroxybiaryl-2-carboxylates
  作者：Prabhakar Ramchandra Joshi、Jagadeesh Babu Nanubolu、Rajeev S. Menon

  DOI：10.1021/acs.orglett.6b00016

  日期：2016.2.19

  Regioselective synthesis of 4-hydroxybiphenyl-2-carboxylates via the base-mediated oxygenative [3 + 3] benzannulation reaction of alpha,beta-unsaturated aldehydes and gamma-phosphonyl crotonates is reported. A hydroxyl group is installed in the final product on the originally phosphorus-bound carbon via a novel oxygenative and dehydrogenative transformation. The reaction proceeds rapidly in an open flask, uses atmospheric oxygen as an oxidant, and affords good yields of substituted biaryl phenols.