4,6-Bis-(3-methyl-but-2-enylsulfanyl)-pyrimidine-5-carbaldehyde | 251989-04-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,6-Bis-(3-methyl-but-2-enylsulfanyl)-pyrimidine-5-carbaldehyde
• 英文别名: 4,6-Bis[(3-methyl-2-butenyl)sulfanyl]-5-pyrimidinecarbaldehyde；4,6-bis(3-methylbut-2-enylsulfanyl)pyrimidine-5-carbaldehyde
• CAS: 251989-04-5
• 化学式: C₁₅H₂₀N₂OS₂
• 分子量: 308.469
• InChiKey: VNNDQZQMABBQDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  吡咯 、 4,6-Bis-(3-methyl-but-2-enylsulfanyl)-pyrimidine-5-carbaldehyde 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 5,10,15,20-Tetrakis-[4,6-bis-(3-methyl-but-2-enylsulfanyl)-pyrimidin-5-yl]-porphyrinogene
  参考文献：
  名称：

  The use of 4,6-disubstituted pyrimidine-5-aldehydes in the synthesis of meso-tetraarylporphyrins

  摘要：

  A new type of double picket-fence porphyrin, bearing pyrimidine rings at the meso-positions was prepared from the corresponding pyrimidine-5-aldehydes using either Rothemund or McDonald condensation reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01571-3
• 作为产物：
  描述：

  4,6-二氯-5-嘧啶甲醛 、 1-溴-3-甲基-2-丁烯 在 硫脲 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以45%的产率得到4,6-Bis-(3-methyl-but-2-enylsulfanyl)-pyrimidine-5-carbaldehyde
  参考文献：
  名称：

  Diastereoselective intramolecular hetero Diels–Alder approach towards polycyclic heterocycles

  摘要：

  Several different heterocyclic aldehydes, derived from pyrazole. pyrimidine, pyridine, indole and thiazole, were converted to polyheterocyclic compounds containing four to seven rings. The key steps in the sequence were a Knoevenagel condensation of the aldehyde and a heterocyclic carbonyl compound, such as pyrazolone and isoxazolone, followed by an intramolecular hetero Diets-Alder reaction. Most final products were isolated with high yield and diastereoselecivity. The isoxazolo fused cycloadducts formed interesting spiro-adducts upon heating. The cis nature of the bridging hydrogens of the heterocycles was evidenced by X-ray diffraction analysis.(dagger) (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01153-x

文献信息

• Diastereoselective intramolecular hetero Diels–Alder approach towards polycyclic heterocycles
  作者：Erik Ceulemans、Marieke Voets、Sabine Emmers、Koen Uytterhoeven、Luc Van Meervelt、Wim Dehaen

  DOI：10.1016/s0040-4020(01)01153-x

  日期：2002.1

  Several different heterocyclic aldehydes, derived from pyrazole. pyrimidine, pyridine, indole and thiazole, were converted to polyheterocyclic compounds containing four to seven rings. The key steps in the sequence were a Knoevenagel condensation of the aldehyde and a heterocyclic carbonyl compound, such as pyrazolone and isoxazolone, followed by an intramolecular hetero Diets-Alder reaction. Most final products were isolated with high yield and diastereoselecivity. The isoxazolo fused cycloadducts formed interesting spiro-adducts upon heating. The cis nature of the bridging hydrogens of the heterocycles was evidenced by X-ray diffraction analysis.(dagger) (C) 2002 Elsevier Science Ltd. All rights reserved.
• The use of 4,6-disubstituted pyrimidine-5-aldehydes in the synthesis of meso-tetraarylporphyrins
  作者：Filip Motmans、Erik Ceulemans、Stefan Smeets、Wim Dehaen

  DOI：10.1016/s0040-4039(99)01571-3

  日期：1999.10

  A new type of double picket-fence porphyrin, bearing pyrimidine rings at the meso-positions was prepared from the corresponding pyrimidine-5-aldehydes using either Rothemund or McDonald condensation reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.