4-acetyl-1,8-bis(dimethylamino)naphthalene | 111967-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-acetyl-1,8-bis(dimethylamino)naphthalene
• 英文别名: Ethanone, 1-[4,5-bis(dimethylamino)-1-naphthalenyl]-；1-[4,5-bis(dimethylamino)naphthalen-1-yl]ethanone
• CAS: 111967-89-6
• 化学式: C₁₆H₂₀N₂O
• mdl: MFCD01305512
• 分子量: 256.348
• InChiKey: HFWWAGBASRAYLW-UHFFFAOYSA-N

物化性质

• 沸点：
  391.3±37.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetyl-1,8-bis(dimethylamino)naphthalene 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2-[4,5-bis(dimethylamino)-1-naphthyl]propene
  参考文献：
  名称：

  peri-Naphthylenediamines

  摘要：

  Tertiary alcohols containing the 4,5-bis(dimethylamino)-1-naphthyl group were synthesized. The carbocations that formed from n-methyl-containing alcohols in an acidic medium underwent smooth E1 elimination to give the corresponding unsaturated derivatives of the "proton sponge" in good yields. At the same time, the carbocation generated from 4-(alpha-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalene was converted into a benzo[a]fluorene derivative as a result of a complex reaction which has been previously unknown in the chemistry of "proton sponges." The structure of the latter derivative was established by X-ray diffraction analysis.

  DOI：

  10.1007/bf02494902
• 作为产物：
  描述：

  N,N-二甲基乙酰胺 、 4-bromo-1,8-bis(dimethylamino)naphthalene 在 正丁基锂 、 四甲基乙二胺 作用下， 以 正己烷 为溶剂， 反应 85.0h， 以20 mg的产率得到4-acetyl-1,8-bis(dimethylamino)naphthalene
  参考文献：
  名称：

  邻二取代萘质子海绵的合成中的非共价Li···H相互作用

  摘要：

  非共价Li···H相互作用被用作在己烷中TMEDA存在下，用n -BuLi对4-lithio-1,8-双（二​​甲基氨基）萘进行第二次锂化的工具。在第二个周边位置，金属化以100％的选择性进行，产率高达90％。在用不同的亲电子试剂淬灭反应物质后，已经以良好的产率制备了一系列的1，8-双（二​​甲基氨基）萘的4，5-二取代的衍生物。

  DOI：

  10.1055/s-0039-1690230

文献信息

• Vistorobskii, N.V.; Pozharskii, A.F., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 7, p. 1353 - 1358
  作者：Vistorobskii, N.V.、Pozharskii, A.F.

  DOI：——

  日期：——
• peri-Naphthylenediamines 18. 1,8-Bis(dimethylamino)-4-vinylnaphthalene
  作者：N. V. Vistorobskii、A. F. Pozharskii

  DOI：10.1007/bf01430735

  日期：1996.9

  The 1-[1,8-bis(dimethylamino)-4-naphthyl]ethyl carbocation generated from the corresponding alcohol in benzene in the presence of Al2O3 undergoes elimination according to the El mechanism to give previously unknown 1,8-bis(dimethylamino)-4-vinylnaphthalene in a good yield: This compound was also synthesized from 1,8-bis(dimethylamino)4-formylnaphthalene by the Wittig reaction. Polymerization of the vinylic derivative obtained was studied.
• Noncovalent Li···H Interaction in the Synthesis of peri-Disubstituted Naphthalene Proton Sponges
  作者：Alexander S. Antonov、Artyom A. Yakubenko

  DOI：10.1055/s-0039-1690230

  日期：2020.1

  Noncovalent Li···H interaction was utilised as a tool for the second lithiation of 4-lithio-1,8-bis(dimethylamino)naphthalene with n-BuLi in the presence of TMEDA in hexane. Metallation proceeds with 100% selectivity in the second peri-position and with up to 90% yield. A series of 4,5-disubstituted derivatives of 1,8-bis(dimethylamino)naphthalene has been prepared in good to excellent yield after

  非共价Li···H相互作用被用作在己烷中TMEDA存在下，用n -BuLi对4-lithio-1,8-双（二​​甲基氨基）萘进行第二次锂化的工具。在第二个周边位置，金属化以100％的选择性进行，产率高达90％。在用不同的亲电子试剂淬灭反应物质后，已经以良好的产率制备了一系列的1，8-双（二​​甲基氨基）萘的4，5-二取代的衍生物。
• peri-Naphthylenediamines
  作者：A. F. Pozharskii、O. V. Ryabtsova、N. V. Vistorobskii、Z. A. Starikova

  DOI：10.1007/bf02494902

  日期：2000.6

  Tertiary alcohols containing the 4,5-bis(dimethylamino)-1-naphthyl group were synthesized. The carbocations that formed from n-methyl-containing alcohols in an acidic medium underwent smooth E1 elimination to give the corresponding unsaturated derivatives of the "proton sponge" in good yields. At the same time, the carbocation generated from 4-(alpha-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalene was converted into a benzo[a]fluorene derivative as a result of a complex reaction which has been previously unknown in the chemistry of "proton sponges." The structure of the latter derivative was established by X-ray diffraction analysis.