4,6-dichloro-2-(p-methoxyphenyl)pyrimidine-5-carbaldehyde | 948863-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,6-dichloro-2-(p-methoxyphenyl)pyrimidine-5-carbaldehyde
• 英文别名: 4,6-Dichloro-2-(4-methoxyphenyl)pyrimidine-5-carbaldehyde；4,6-dichloro-2-(4-methoxyphenyl)pyrimidine-5-carbaldehyde
• CAS: 948863-46-5
• 化学式: C₁₂H₈Cl₂N₂O₂
• 分子量: 283.114
• InChiKey: VLVCPMIWUANLKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-2-(p-methoxyphenyl)pyrimidine-5-carbaldehyde 、 2-(二吡咯-2-基)甲基三甲苯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  meso-Pyrimidinyl-Substituted A₂B-Corroles

  摘要：

  [GRAPHICS]meso-Pyrimidinyl-substituted A(2)B-corroles were synthesized in good yields by condensation of 5-mesityldipyrromethane and 2-substituted 4,6-dichloropyrimidine-5-carbaldehydes. A simple reduction of the amount of Lewis acid (BF3 center dot OEt2) resulted in the formation of A(2)B-corroles, which was optimized to maximize the corrole yield. Nucleophilic aromatic substitution, Suzuki, and Stille cross-coupling reactions were performed on the Cu-metalated pyrimidinylcorroles to obtain sterically encumbered triarylcorroles, while the substitution pattern at the 2-position of the pyrimidinyl substituent was altered through Liebeskind-Srogl cross-couplings.

  DOI：

  10.1021/ol071226a
• 作为产物：
  描述：

  Vilsmeier-Haack reagent 、 4,6-dihydroxy-2-(p-methoxyphenyl)pyrimidine 反应 5.5h， 以57%的产率得到4,6-dichloro-2-(p-methoxyphenyl)pyrimidine-5-carbaldehyde
  参考文献：
  名称：

  meso-Pyrimidinyl-Substituted A₂B-Corroles

  摘要：

  [GRAPHICS]meso-Pyrimidinyl-substituted A(2)B-corroles were synthesized in good yields by condensation of 5-mesityldipyrromethane and 2-substituted 4,6-dichloropyrimidine-5-carbaldehydes. A simple reduction of the amount of Lewis acid (BF3 center dot OEt2) resulted in the formation of A(2)B-corroles, which was optimized to maximize the corrole yield. Nucleophilic aromatic substitution, Suzuki, and Stille cross-coupling reactions were performed on the Cu-metalated pyrimidinylcorroles to obtain sterically encumbered triarylcorroles, while the substitution pattern at the 2-position of the pyrimidinyl substituent was altered through Liebeskind-Srogl cross-couplings.

  DOI：

  10.1021/ol071226a

文献信息

• Synthetic, Structural, and Photophysical Exploration of<i>meso</i>-Pyrimidinyl-Substituted AB₂-Corroles
  作者：Thien H. Ngo、Fausto Puntoriero、Francesco Nastasi、Koen Robeyns、Luc Van Meervelt、Sebastiano Campagna、Wim Dehaen、Wouter Maes

  DOI：10.1002/chem.201000008

  日期：2010.5.17

  distances and a saddled corrole plane. The absorption spectra and photophysical properties of some representative free‐base AB2‐pyrimidinylcorroles were examined in depth. The absorption spectra displayed typical corrole features: intense spin‐allowed π–π* bands, which can be classified as Soret‐ and Q‐type bands. The photophysical properties, investigated both in fluid solution at room temperature

  从5-间苯二甲酰氯甲烷和各种2-取代的4,6-二氯嘧啶-5-甲醛开始，有效合成了内消旋-嘧啶基取代的AB 2-苯酚。所述corrole产量通过路易斯酸催化剂（BF的量的优化显著增强3 ⋅ OET 2）。嘧啶基Corroles相对于其他内消旋体的主要优势三芳基cor杂醇是它们广泛的功能化可能性，已通过亲核和亲电芳族取代以及Pd催化的交叉偶联反应进行了探索。氯官能团的逐步取代得到不对称取代的嘧啶基Corroles。由于游离碱腐蚀物大环化合物的不稳定性，腐蚀物外围的功能化优先在金属铜化的对应物上进行。但是，通过可逆的序列Cu插入和随后的还原性脱金属操作，可以轻松获得功能化的游离碱AB 2-嘧啶基硬脂醇。因此，AB 2-嘧啶基Corroles被认为是通向更复杂的Corrole系统的高度通用的平台。双（4叔）的X射线分析-2-丁基苯氧基）取代的铜-嘧啶基corrole表现出了铜-corrole的典型