4,5-bis(dimethylamino)-1-naphthyllithium | 372988-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-bis(dimethylamino)-1-naphthyllithium
• 英文别名: 4-lithio-1,8-bis(dimethylamino)-naphthalene
• CAS: 372988-68-6
• 化学式: C₁₄H₁₇LiN₂
• 分子量: 220.243
• InChiKey: YAYHUHVXWLNHFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,5-bis(dimethylamino)-1-naphthyllithium 在 碘 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以87%的产率得到4-iodo-1,8-bis(dimethylamino)naphthalene
  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
• 作为产物：
  描述：

  1,8-双二甲氨基萘 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 2.5h， 生成 4,5-bis(dimethylamino)-1-naphthyllithium
  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

• Aggregation Behavior of Lithionaphthalenes in Solution: Experimental and Theoretical Study
  作者：Alexander S. Antonov、Valerii V. Karpov、Elena Yu. Tupikina、Peter M. Tolstoy、Mikhail A. Vovk

  DOI：10.1021/acs.organomet.0c00524

  日期：2020.10.26

  The aggregation of a series of mono- and dilithionaphthalenes in THF solutions in the presence of tetramethylethylenediamine (TMEDA) and pentamethyldiethylenetriamine (PMDTA) was studied by NMR spectroscopy and quantum chemical calculations. The stability of dimeric species in diluted solutions as well as reasons of their disaggregation in some cases has been discussed. For the lithioderivatives of

  通过NMR光谱和量子化学计算研究了在四甲基乙二胺（TMEDA）和五甲基二乙三胺（PMDTA）存在下在THF溶液中一系列单和双锂酞菁的聚集。讨论了二聚体在稀释溶液中的稳定性，以及在某些情况下其分解的原因。对于1,8-双（二​​甲基氨基）萘（DMAN）的硫代衍生物，在取代基的空间压力下，NMe 2基团在萘核的邻位与锂原子配位的可能性得到了证明。首次在1 H，13 C和7下研究了二锂基萘Li NMR光谱。结果表明，尽管β-二锂基萘在溶液中形成低聚物，但α-二锂基萘仅作为单体形式存在，每个锂原子均在两个周边位置配位。
• VISTOROBSKIJ, N. V.;POZHARSKIJ, A. F., ZH. ORGAN. XIMII, 25,(1989) N0, S. 2154-2161
  作者：VISTOROBSKIJ, N. V.、POZHARSKIJ, A. F.

  DOI：——

  日期：——