1,2,2,3-tetramethyl-2,3-dihydroperimidin-6-carboxaldehyde | 253780-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,2,3-tetramethyl-2,3-dihydroperimidin-6-carboxaldehyde
• 英文别名: 1,2,2,3-tetramethyl-2,3-dihydroperimidine-6-carbaldehyde；1,2,2,3-tetramethylperimidine-6-carbaldehyde
• CAS: 253780-84-6
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: DMZKUCIYVLWYRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  23.55
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,2,2,3-tetramethyl-2,3-dihydroperimidin-6-carboxaldehyde 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以100%的产率得到1,2,2,3-tetramethyl-2,3-dihydro-1H-perimidine-6-ylmethanol
  参考文献：
  名称：

  Resonance-stabilized α-naphthylmethyl carbocations and spiro compounds based thereon: VII. Transformations of α-naphthylmethyl carbocations stabilized by one electron-donor group or peri-fused heteroring

  摘要：

  1-Hydroxymethyl- and 1-alkoxymethylnaphthalenes containing dimethylamino and methoxy groups or a heteroring in positions 4 and 5 react with protic and Lewis acids to give 1-naphthylmethyl carbocations. Reactions of the latter with the initial alcohol molecule lead to the formation of oligomerization or dehydrogenation (to aldehyde) products or the corresponding dinaphthylmethanes. In some cases, the process was accompanied by cyclodimerization to form cyclohexadienone spiro derivatives in a small yield.

  DOI：

  10.1134/s107042800603002x
• 作为产物：
  描述：

  1,2,2,3-tetramethyl-2,3-dihydro-1H-perimidine-6-ylmethanol 在 aluminum oxide 作用下， 以 苯 为溶剂， 反应 2.0h， 以16%的产率得到
  参考文献：
  名称：

  Resonance-stabilized α-naphthylmethyl carbocations and spiro compounds based thereon: VII. Transformations of α-naphthylmethyl carbocations stabilized by one electron-donor group or peri-fused heteroring

  摘要：

  1-Hydroxymethyl- and 1-alkoxymethylnaphthalenes containing dimethylamino and methoxy groups or a heteroring in positions 4 and 5 react with protic and Lewis acids to give 1-naphthylmethyl carbocations. Reactions of the latter with the initial alcohol molecule lead to the formation of oligomerization or dehydrogenation (to aldehyde) products or the corresponding dinaphthylmethanes. In some cases, the process was accompanied by cyclodimerization to form cyclohexadienone spiro derivatives in a small yield.

  DOI：

  10.1134/s107042800603002x

文献信息

• Near-Infrared Fluorescent 2,3-Dicyanopyrazines
  作者：Masaki Matsui、Takaya Maehashi、Kazumasa Funabiki

  DOI：10.1246/bcsj.80.999

  日期：2007.5.15

  Novel non-ionic near-infrared (NIR) fluorescent 2,3-dicyanopyrazines were prepared. 5-[6-(9-julolidyl)-1,3,5-hexatrienyl]- and 5-[8-(9-julolidyl)-1,3,5,7-octatetraenyl]-2,3-dicyanopyrazines showed fluorescence maxima (Fmax) at 716 and 751 nm with fluorescence quantum yields (Φf) 0.12 and 0.03 in toluene, respectively. MO calculations showed that these compounds have an intramolecular charge-transfer chromophoric system from the julolidyl to dicyanopyrazine moieties. The calculations also showed that since the HOMO energy level was unstabilized, and at the same time, the LUMO energy level was stabilized by expanding the conjugated system at 5-position, NIR fluorescent derivatives were obtained. They showed clear positive solvatochromism in the fluorescence spectroscopy. The fluorescence intensity drastically decreased in polar solvents.

  制备了新型非离子近红外（NIR）荧光 2,3-二氰基吡嗪。5-[6-(9-julolidyl)-1,3,5-hexatrienyl]-和 5-[8-(9-julolidyl)-1,3,5,7-octatetraenyl]-2,3-二氰基吡嗪在甲苯中的荧光最大值（Fmax）分别为 716 纳米和 751 纳米，荧光量子产率（Φf）分别为 0.12 和 0.03。MO 计算表明，这些化合物具有一个分子内电荷转移的发色系统，即从巨烷基到二氰基吡嗪的电荷转移。计算还表明，由于 HOMO 能级不稳定，同时通过扩大 5 位共轭体系使 LUMO 能级稳定，因此得到了近红外荧光衍生物。它们在荧光光谱中显示出明显的正溶色性。在极性溶剂中，荧光强度急剧下降。
• Heterocyclic analogs of pleiadiene. 67. Formylation of perimidones, 2,3-dihydroperimidines, and perimidines
  作者：A. F. Pozharskii、E. A. Filatova、N. V. Vistorobskii、I. V. Borovlev

  DOI：10.1007/bf02259363

  日期：1999.3
• peri-Naphthylenediamines: XL. Solvatochromism of 1-methyl-4-[2-(1-naphthyl)ethenyl]pyridinium salts, including that containing “proton sponge” residue
  作者：A. F. Pozharskii、N. V. Vistorobskii、A. A. Bardin、E. A. Filatova

  DOI：10.1134/s1070428006010209

  日期：2006.1

  A number of 1-methyl-4-[2-(1-naphthyl)ethenyl]pyridinium salts were synthesized by condensation of 1,4-dimethylpyridinium iodide with naphthalene-1-carbaldehydes containing dimethylamino groups in positions 4 and 5. The obtained salts are characterized by negative solvatochromism which is the most pronounced for those possessing 1,8-bis(dimethylamino)naphthalene ("proton sponge") and 1,2,2,3-tetramethyl-2,3-di-hydroperimidine residues.