6,7,5'-tris(dimethylamino)-1,1',3,4'-tetrahydrospiro[phenalene-1,1'-naphthalene]-4'-one | 135260-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 6,7,5'-tris(dimethylamino)-1,1',3,4'-tetrahydrospiro[phenalene-1,1'-naphthalene]-4'-one
• 英文别名: 5,6',7'-tris(dimethylamino)-2',3'-dihydro-4H-spiro[naphthalene-1,1'-phenalen]-4-one；6,7,8'-tris(dimethylamino)spiro[1,2-dihydrophenalene-3,4'-naphthalene]-1'-one
• CAS: 135260-62-7
• 化学式: C₂₈H₃₁N₃O
• 分子量: 425.574
• InChiKey: BUCXQKQWSZDMOG-UHFFFAOYSA-N

物化性质

• 沸点：
  613.2±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-ethoxymethyl-N,N,N',N'-tetramethylnaphthalene-1,8-diamine 在 氢溴酸 作用下， 以78%的产率得到6,7,5'-tris(dimethylamino)-1,1',3,4'-tetrahydrospiro[phenalene-1,1'-naphthalene]-4'-one
  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

• Resonance-stabilized ?-naphthylmethyl carbocations and derived spiro compounds 4. T-ansformations of 4-dimethylamino-5-methoxynaphthylmethyl carbocation in the presence of protic and Lewis acids. The formation of an asymmetrical spiro compound
  作者：A. F. Pozharskii、N. V. Vistorobskii、M. I. Rudnev、A. I. Chernyshev

  DOI：10.1007/bf01457780

  日期：1996.8

  carbocation generated from 1-hydroxy methyl-4-dimethylamino-5-methoxynaphthalene in trifluoroacetic acid behaves as both diene and dienophile and undergoes (4π + 2π) cycloaddition to give an asymmetrical spiro compound. The other reaction product is 4,4'-bis(dimethylamino)-5,5'-dimethoxy 1,l'-dinaphthylmethane, which is formedvia ipso-substitution of the hydroxymethyl group in the initial alcohol. When this cation

  摘要 1-羟基甲基-4-二甲氨基-5-甲氧基萘在三氟乙酸中生成的4-二甲基（氨基-5-甲氧基萘甲基碳正离子）既是二烯又是亲二烯体，经过（4π+2π）环加成生成不对称螺环化合物。反应产物是 4,4'-双(二甲氨基)-5,5'-二甲氧基 1,1'-二萘甲烷，它是通过初始醇中的羟甲基同位取代形成的。当这种阳离子在 Al2O3 上生成时，4 -二甲氨基-5-甲氧基1-萘醛与取代的二萘甲烷一起形成。
• Vistorobskii, N. V.; Pozharskii, A. F.; Chernyschev, A. I., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 5.2, p. 895 - 903
  作者：Vistorobskii, N. V.、Pozharskii, A. F.、Chernyschev, A. I.、Shorshnev, S. V.

  DOI：——

  日期：——