3,5-dimethyl-N,N-diethylaniline | 3995-39-9

• 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: 3,5-dimethyl-N,N-diethylaniline
• 英文别名: N,N-diethyl-3,5-dimethylaniline；N,N-diethyl-3,5-xylidene；N,N-diethyl-m-xylidine；N,N-diethyl-3,5-dimethyl-aniline；N,N-Diaethyl-3,5-dimethyl-anilin；3,5-Dimethyl-N,N-diethylanilin；Benzenamine, N,N-diethyl-3,5-dimethyl-
• CAS: 3995-39-9
• 化学式: C₁₂H₁₉N
• 分子量: 177.29
• InChiKey: VFNOZYFHJTZTLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 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：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-N,N-diethylaniline 在 盐酸 、 ammonium peroxydisulfate 、 锌 、 sodium nitrite 作用下， 以 ammonium hydroxide 、 水 、 丙酮 为溶剂， 反应 2.5h， 生成 4-(4-diethylamino-2,6-dimethylphenylimino)-1,4-dihydronaphthylidenemalononitrile
  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
• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 在 三氟化硼 作用下， 以 环己烷 为溶剂， 反应 15.5h， 生成 3,5-dimethyl-N,N-diethylaniline
  参考文献：
  名称：

  Bunce, Nigel J.; Cater, Stephen R., Journal of the Chemical Society. Perkin transactions II, 1986, p. 169 - 174

  摘要：

  DOI：
• 作为试剂：
  描述：

  naphthalene-1,8-diylbis(diphenylmethylium) diperchlorate 在 3,5-dimethyl-N,N-diethylaniline 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,1,2,2-tetraphenylacenaphthene
  参考文献：
  名称：

  1,8-Bis(diphenylmethylium)naphthalenediyl Dication as an Organic Oxidant:  Synthesis of Benzidines via Self-Coupling of N,N-Dialkylanilines

  摘要：

  1,8-Bis(diphenylmethylium)naphthalenediyl dications promoted oxidative coupling of various N,N-dialkylanilines to afford the corresponding para-coupled bisanilines, benzidines, in good to excellent yield. The dications were readily prepared from a cyclic ether precursor, derived from 1,8-dibromonaphthalene, via deoxygenation with a silylating reagent in 1,1,1,3,3,3-hexafluoro-2-propanol under anhydrous conditions.

  DOI：

  10.1021/ol048058w

文献信息

• A New Organic Two‐Electron Oxidant: 9,10‐Diaryl‐9,10‐dihydroanthracene‐9,10‐bis(ylium)
  作者：Junji Ichikawa、Hiroyuki Tanabe、Suguru Yoshida、Takaharu Kawai、Masahiko Shinjo、Takeshi Fujita

  DOI：10.1002/asia.201300710

  日期：2013.11

  Strong as an Ox: A dicationic compound with a 9,10‐dihydroanthracene skeleton has been produced from the corresponding 9,10‐dialkoxy‐9,10‐dihydroanthracene, which was readily prepared from anthraquinone. The dication functions as a powerful two‐electron oxidant, comparable to aminium cation radicals, and has been employed in oxidative processes such as the self‐coupling of anilines and naphthols, and

  像牛一样强壮：从9,10-二烷氧基-9,10-二氢蒽制得的具有9,10-二氢蒽骨架的双效化合物可以很容易地从蒽醌制备。该指示剂可作为强大的双电子氧化剂，与铵阳离子自由基相当，并已用于氧化过程，例如苯胺和萘的自偶联，以及对甲氧基苄基（PMB）醚的氧化脱保护。
• Cu(ii)-catalyzed C–H (SP3) oxidation and C–N cleavage: base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source
  作者：Lei Zhang、Chen Peng、Dan Zhao、Yue Wang、Hai-Jian Fu、Qi Shen、Jian-Xin Li

  DOI：10.1039/c2cc32009f

  日期：——

  Base-switched methylenation and formylation using tetramethylethylenediamine (TMEDA) as a carbon source have been achieved under mild conditions, catalyzed by CuCl(2), with atmospheric oxygen as oxidant. Bisindolylmethanes, diphenylmethanes and 3-formylindoles were synthesized with excellent regioselectivity and good yield.

  使用四甲基乙二胺（TMEDA）作为碳源的碱转换的甲基化和甲酰化反应已在温和的条件下实现，由CuCl（2）催化，大气中的氧气作为氧化剂。合成了双吲哚甲烷，二苯基甲烷和3-甲酰基吲哚，具有良好的区域选择性和良好的收率。
• A metal- and oxidizing-reagent-free anodic <i>para</i>-selective amination of anilines with phenothiazines
  作者：Yan-Chen Wu、Shuai-Shuai Jiang、Ren-Jie Song、Jin-Heng Li

  DOI：10.1039/c9cc01332f

  日期：——

  A highly para-selective amination of anilines with phenothiazines for producing various functionalized 10-aryl-10H-phenothiazines is reported.

  一种高度para选择性的苯胺与吩噻嗪的胺化反应，用于制备各种官能化的10-芳基-10H-吩噻嗪。
• CuBr/H₂O₂-Mediated Oxidative Coupling of<i>N</i>,<i>N</i>-Dialkylarylamines in ­Water: A Practical Synthesis of Benzidine Derivatives
  作者：Chanjuan Xi、Yanfeng Jiang、Xianghua Yang

  DOI：10.1055/s-2005-868490

  日期：——

  CuBr/H2O2 was deployed into mediating the oxidative coupling reaction of N,N-dialkylarylamines in water, which gave benzidine derivatives in an economically and environmentally ­satisfying manner.

  CuBr/H2O2 被用于介导 N,N-二烷基芳胺在水中的氧化偶联反应，从而以经济和环保的方式得到联苯胺衍生物。
• Vernaudon, Pascal; Rajoharison, Harivelo G.; Roussel, Chritian, Bulletin de la Societe Chimique de France, 1987, # 1, p. 205 - 211
  作者：Vernaudon, Pascal、Rajoharison, Harivelo G.、Roussel, Chritian

  DOI：——

  日期：——