1,8-bis(dimethylamino)-4-naphthyltrimethylsilane

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,8-bis(dimethylamino)-4-naphthyltrimethylsilane
• 英文别名: 4-trimethylsilyl-1,8-bis(dimethylamino)naphthalene；1-N,1-N,8-N,8-N-tetramethyl-4-trimethylsilylnaphthalene-1,8-diamine
• 化学式: C₁₇H₂₆N₂Si
• 分子量: 286.492
• InChiKey: AQRQSWGSAGYTSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-bromo-1,8-bis(dimethylamino)naphthalene 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 5.0h， 生成 1,8-bis(dimethylamino)-4-naphthyltrimethylsilane
  参考文献：
  名称：

  摘要：

  The 4-deuterio, 4-methyl, 4-iodo, 4-methylthio, 4-trimethylsilyl, and 4-ethoxycarbonyl derivatives of 1,8-bis(dimethylamino)naphthalene ("proton sponge") and some related alcohols were prepared by the reactions of 4,5-bis(dimethylamino)-1-naphthyllithium or 4.5-bis(dimethylamino)-1-naphthylmagnesittm bromide with the corresponding electrophilic reagents. New representatives of double "proton sponges" with the structures of 1,1 ' -binaphthyl ketone and 1,1 ' -binaphthylmethanol were synthesized. The pK(a) values of selected compounds in DMSO were measured by competitive protonation.

  DOI：

  10.1023/a:1011311226664

文献信息

• 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。
• ——
  作者：O. V. Ryabtsova、A. F. Pozharskii、V. A. Ozeryanskii、N. V. Vistorobskii

  DOI：10.1023/a:1011311226664

  日期：——

  The 4-deuterio, 4-methyl, 4-iodo, 4-methylthio, 4-trimethylsilyl, and 4-ethoxycarbonyl derivatives of 1,8-bis(dimethylamino)naphthalene ("proton sponge") and some related alcohols were prepared by the reactions of 4,5-bis(dimethylamino)-1-naphthyllithium or 4.5-bis(dimethylamino)-1-naphthylmagnesittm bromide with the corresponding electrophilic reagents. New representatives of double "proton sponges" with the structures of 1,1 ' -binaphthyl ketone and 1,1 ' -binaphthylmethanol were synthesized. The pK(a) values of selected compounds in DMSO were measured by competitive protonation.