4-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)benzaldehyde | 850222-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)benzaldehyde
• 英文别名: 4-[(Bicyclo[2.2.1]hept-5-en-2-yl)methoxy]benzaldehyde；4-(2-bicyclo[2.2.1]hept-5-enylmethoxy)benzaldehyde
• CAS: 850222-68-3
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: LGWVOAFXHXLMAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)benzaldehyde 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 28.0h， 生成 2,3-bis[4-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)benzylamino]but-2-enedinitrile
  参考文献：
  名称：

  ROM Polymerization-Capture-Release Strategy for the Chromatography-Free Synthesis of Novel Unsymmetrical Porphyrazines

  摘要：

  Crossover-Linstead macrocyclization reactions of two norbornenyl-tagged diaminomaleonitriles with dipropylmaleonitrile gave access to crude mixtures of porphyrazines containing diamino-hexapropyl-porphyrazine magnesium complexes. The mixtures were subjected to ring-opening metathesis polymerization to yield the insoluble diaminoporphyrazine-functionalized polymers. Acid-mediated cleavage from the polymer backbone followed by acylation of the resultant sensitive macrocyclic diamines gave monoacetyl-, monotrifluoroacetyl-, and ditrifluoroacetyl-substituted porphyrazinedi-amines. Conversion of these amido-porphyrazines to the corresponding zinc macrocycles and studies of their electronic absorption and emission spectra, electrochemistry, and photophysics are described.

  DOI：

  10.1021/jo047792q
• 作为产物：
  描述：

  2-Hydroxymethyl-bicyclo<2.2.1>hept-5-en-p-toluolsulfonat 、 对羟基苯甲醛 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以96%的产率得到4-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)benzaldehyde
  参考文献：
  名称：

  ROM Polymerization-Capture-Release Strategy for the Chromatography-Free Synthesis of Novel Unsymmetrical Porphyrazines

  摘要：

  Crossover-Linstead macrocyclization reactions of two norbornenyl-tagged diaminomaleonitriles with dipropylmaleonitrile gave access to crude mixtures of porphyrazines containing diamino-hexapropyl-porphyrazine magnesium complexes. The mixtures were subjected to ring-opening metathesis polymerization to yield the insoluble diaminoporphyrazine-functionalized polymers. Acid-mediated cleavage from the polymer backbone followed by acylation of the resultant sensitive macrocyclic diamines gave monoacetyl-, monotrifluoroacetyl-, and ditrifluoroacetyl-substituted porphyrazinedi-amines. Conversion of these amido-porphyrazines to the corresponding zinc macrocycles and studies of their electronic absorption and emission spectra, electrochemistry, and photophysics are described.

  DOI：

  10.1021/jo047792q

文献信息

• ROM Polymerization−Capture−Release:  Application to the Synthesis of Unsymmetrical Porphyrazinedithiols and Peripherally Metalated Derivatives
  作者：Matthew J. Fuchter、Brian M. Hoffman、Anthony G. M. Barrett

  DOI：10.1021/jo050369c

  日期：2005.6.1

  Crossover Linstead macrocyclization of a doubly norbornenyl-functionalized dimercaptornaleonitrile with dipropylmaleonitrile gave a crude mixture of porphyrazines containing the hexapropylpor-phyrazinedithiol magnesium complex. The mixture was subjected to ring-opening metathesis polymerization to yield the insoluble porphyrazinedithiol-functionalized polymers. Cleavage from the polymer backbone using mercury(II) acetate followed by reaction with electrophiles gave access to a range of thioporphyrazinedithiol derivatives including solitaire porphyrazines. Studies into the possible uses of hexapropyl-2,3-di-(carboxymethylthio)porphyrazine in sensing metal cations in solution are described.
• ROM Polymerization-Capture-Release Strategy for the Chromatography-Free Synthesis of Novel Unsymmetrical Porphyrazines
  作者：Matthew J. Fuchter、Benjamin J. Vesper、Karen A. Murphy、Hazel A. Collins、David Phillips、Anthony G. M. Barrett、Brian M. Hoffman

  DOI：10.1021/jo047792q

  日期：2005.4.1

  Crossover-Linstead macrocyclization reactions of two norbornenyl-tagged diaminomaleonitriles with dipropylmaleonitrile gave access to crude mixtures of porphyrazines containing diamino-hexapropyl-porphyrazine magnesium complexes. The mixtures were subjected to ring-opening metathesis polymerization to yield the insoluble diaminoporphyrazine-functionalized polymers. Acid-mediated cleavage from the polymer backbone followed by acylation of the resultant sensitive macrocyclic diamines gave monoacetyl-, monotrifluoroacetyl-, and ditrifluoroacetyl-substituted porphyrazinedi-amines. Conversion of these amido-porphyrazines to the corresponding zinc macrocycles and studies of their electronic absorption and emission spectra, electrochemistry, and photophysics are described.