2,6-dimethyl-4-(diethylamino)aniline | 2359-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dimethyl-4-(diethylamino)aniline
• 英文别名: 4-Diethylamino-2,6-dimethylaniline；N⁴,N⁴-diethyl-2,6-dimethyl-p-phenylenediamine；N⁴,N⁴-Diaethyl-2,6-dimethyl-p-phenylendiamin；3.5-Dimethyl-N.N-diethyl-p-phenylendiamin；4-Amino-3,5-dimethyl-N-diethyl-anilin；2,6-Dimethyl-4-diethylamino-anilin；4-N,4-N-diethyl-2,6-dimethylbenzene-1,4-diamine
• CAS: 2359-40-2
• 化学式: C₁₂H₂₀N₂
• mdl: MFCD09035947
• 分子量: 192.304
• InChiKey: YTEPJDDAQWIJEP-UHFFFAOYSA-N

物化性质

• 沸点：
  321.8±37.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-4-(diethylamino)aniline 生成 N-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-N-ethylethanaminium
  参考文献：
  名称：

  N-取代的醌单亚胺和二亚胺的脱氨活化参数及机理

  摘要：

  使用紫外光谱，通过停止流方法在278至323 K之间的温度，pH在1至9的pH范围内，通过水溶液测量了六个N-取代的醌单亚胺的脱氨速率。观测到的速率常数由k = k '[H 2 O] + k ” [OH – ]给出；ķ '和ķ “由12个数量级不同。k ′和k ′的激活焓几乎相等。活化的熵是强负对ķ '和强阳性ķ “。酸和碱脱氨的活化参数还测量了N-取代的醌二亚胺。关于活化熵，发现与醌单亚胺相似的结果。对于所有脱氨基，提出了具有预先溶剂化平衡的通用机理。

  DOI：

  10.1039/p29800001601
• 作为产物：
  描述：

  3,5-dimethyl-N,N-diethylaniline 在 盐酸 、 锌 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2,6-dimethyl-4-(diethylamino)aniline
  参考文献：
  名称：

  Experimental and theoretical study of near-infrared absorbing naphthoquinone methide dyes with a nonplanar geometry

  摘要：

  The bathochromic shift of the near-infrared absorption spectra of naphthoquinone methide dyes has been observed as a function of increased steric hindrance between the quinone imine and aniline segments. This novel shift that results from the loss of planarity has been examined by means of semiempirical INDO/S and AM1 models. Based on the configuration interaction (CI) analysis, the observed transitions in both the near-infrared and UV regions have been assigned. The introduction of an acetylamino group at the 2-position of aniline ring has caused a bathochromic shift with a remarkable increase in molecular extinction coefficient. In order to interpret these results, both an electronic factor and a steric effect have been analyzed. This interesting color-structure relationship of a nonplanar chromophoric system has been elucidated.

  DOI：

  10.1021/ja00008a012

文献信息

• Novel syntheses of di-iminonaphthalene type near-i.r. dyes
  作者：Yuji Kubo、Minoru Kuwana、Ken Okamoto、Katsuhira Yoshida

  DOI：10.1039/c39890000855

  日期：——

  New di-iminonaphthalene type near-i.r. dyes are conveniently synthesized by condensing 1-naphthylcyanamide with p-N,N-dialkylaminoanilines in the presence of an oxidising agent; their absorption properties are discussed.

  新二iminonaphthalene型近红外染料被冷凝1- naphthylcyanamide与方便地合成p - Ñ，Ñ -dialkylaminoanilines在氧化剂的存在; 讨论了它们的吸收性能。
• Tuning the Electronic Properties of N-Heterocyclic Carbenes
  作者：Steffen Leuthäußer、Daniela Schwarz、Herbert Plenio

  DOI：10.1002/chem.200700228

  日期：2007.8.27

  The electron-donating properties of N-heterocyclic carbenes ([N,N'-bis(2,6-dimethylphenyl)imidazol]-2-ylidene and the respective dihydro ligands) with 4,4'-R-substituted aryl rings (4,4'-R=NEt2, OC(12)H(25), Me, H, Br, S(4-tolyl), SO(4-tolyl), SO2(4-tolyl)) were studied. Twelve new N-heterocyclic carbene (NHC) ligands were synthesized as well as the respective iridium complexes [IrCl(cod)(NHC)] and

  具有4,4'-R-取代的芳基环的N-杂环卡宾（[N，N'-双（2,6-二甲基苯基）咪唑] -2-亚烷基和相应的二氢配体）的供电子性能（4 ，4'-R = NEt2，OC（12）H（25），Me，H，Br，S（4-tolyl），SO（4-tolyl），SO2（4-tolyl））。合成了十二个新的N-杂环卡宾（NHC）配体以及相应的铱配合物[IrCl（cod）（NHC）]和[IrCl（CO）2（NHC）]。循环伏安法（DeltaE1 / 2）和IR（nu（CO））可用于测量卡宾配体的给电子性。用吸电子取代基（4-R = -SO（2）Ar，DeltaE1 / 2 = + 0.92 V）修饰4位化合物，得到的NHC配体实际上具有与[IrCl（cod）的三烷基膦相同的给电子能力）（PCy3）]（DeltaE1 / 2 = + 0.95 V），
• π-Face Donor Properties of N-Heterocyclic Carbenes in Grubbs II Complexes
  作者：Steffen Leuthäußer、Volker Schmidts、Christina M. Thiele、Herbert Plenio

  DOI：10.1002/chem.200800139

  日期：2008.6.20

  NEt2, H) and in the cathodic isomer the electron rich aryl ring is located above the Ru=CHPh unit. This orientational effect provides clear evidence for strong pi-pi through-space interactions in the RuIII complexes, assuming that the alternative through-bond transfer of electron density is equally efficient in both isomers.

  18个带有4,4'-R取代的芳基环的N-杂环卡宾（N，N'-双（2,6-二甲基苯基）咪唑）-2-亚烷基和各自的二氢配体）的供电子特性使用电化学技术研究了各自的Grubbs II配合物中的4'-R = NEt2，OMe，Me，H，SMe，F，Cl，Br，I）。4-R取代基的性质对DeltaE1 / 2 = +0.196和+0.532 V之间的RuII / III氧化还原电势有很大的影响。4-R不等于4-R'的三种不对称Grubbs II配合物也是合成的。动态NMR光谱显示（NHC）C-Ru键（在333 K处DeltaG = 89 kJ mol（-1）周围）受限制的旋转，分别导致两种阻转异构体，其异构体比率接近于1。每种异构体，即4-R / 4-R'的两个方向 相对于R ＝ CHPh单元的取代的均三环，引起不同的氧化还原电势（4-R ＝ NEt 2，4-R′＝ Br：DeltaE1 / 2 ＝
• Kubo, Yuji; Kuwana, Minoru; Okamoto, Ken, Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 1975 - 1978
  作者：Kubo, Yuji、Kuwana, Minoru、Okamoto, Ken、Yoshida, Katsuhira

  DOI：——

  日期：——
• Chemical Constitution, Electrochemical, Photographic and Allergenic Properties of p-Amino-N-dialkylanilines¹
  作者：R. L. Bent、J. C. Dessloch、F. C. Duennebier、D. W. Fassett、D. B. Glass、T. H. James、D. B. Julian、W. R. Ruby、J. M. Snell、J. H. Sterner、J. R. Thirtle、P. W. Vittum、A. Weissberger

  DOI：10.1021/ja01151a037

  日期：1951.7