苯胺,3,4-二甲基-N-(2-甲基丙基)- | 105336-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯胺,3,4-二甲基-N-(2-甲基丙基)-
• 英文名称: N-isopropyl-3,4-dimethylaniline
• 英文别名: N-sec-Butyl-3,4-xylidin；N-isobutyl-3,4-dimethylaniline；3,4-dimethyl-N-(2-methylpropyl)aniline
• CAS: 105336-24-1
• 化学式: C₁₂H₁₉N
• mdl: MFCD11144373
• 分子量: 177.29
• InChiKey: AEYPGCGYILRJRO-UHFFFAOYSA-N

物化性质

• 沸点：
  82-86 °C(Press: 0.25 Torr)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  苯胺,3,4-二甲基-N-(2-甲基丙基)- 在 sodium dithionite 、 sodium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.5h， 生成 N(3)-methyl,N(10)-isobutyl-7,8-dimethylisoalloxazine
  参考文献：
  名称：

  Model Systems for Flavoenzyme Activity:  One- and Two-Electron Reduction of Flavins in Aprotic Hydrophobic Environments

  摘要：

  The processes occurring during the electrochemically irreversible reduction of flavins in aprotic organic medium have been the cause of considerable controversy. To provide insight into these events we have investigated the reduction of flavins alkylated at N(3). We have demonstrated that the reversible reduction of N(3)-methylated flavin can be converted to the irreversible reduction observed with unalkylated flavins through addition of the weak external proton donor phthalimide. Proton transfer to the flavin radical anion generated at the electrode leads to partial formation of the neutral flavin radical; which is instantaneously further reduced to the fully reduced flavin anion. This mirrors the reduction of unalkylated flavins, where the proton source is the imide proton at N(3) of fully oxidized flavin in bulk solution. Simultaneous electrochemistry and EPR experiments confirm the disappearance of electrogenerated flavin radical anion both methylated and non-methylated at N(3), upon addition of phthalimide. UV/vis spectroelectrochemistry likewise confirmed the generation of the radical anion in the absence of proton donors and fully reduced flavin in the presence of proton donors.

  DOI：

  10.1021/ja963704a
• 作为产物：
  描述：

  异丁腈 、 4-硝基邻二甲苯 在 10% palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 以63%的产率得到苯胺,3,4-二甲基-N-(2-甲基丙基)-
  参考文献：
  名称：

  使用腈作为烷基化试剂的芳香硝基化合物的一锅还原单-N-烷基化

  摘要：

  摘要 说明了在常压和环境温度下在四氢呋喃中，在 H2 和 10% Pd/C 催化剂存在下，由各种硝基芳烃和腈合成芳香仲胺的一锅法、简单、选择性和高效的方案。已经检查了该方法的范围和局限性。

  DOI：

  10.1080/00397911.2010.493627

文献信息

• Synthesis and Structure-Activity Relationships of Substituted 2-((2-Imidazolylsulfinyl)methyl)anilines as a New Class of Gastric H+/K+ -ATPase Inhibitors. II.
  作者：Tomio YAMAKAWA、Hitoshi MATSUKURA、Yutaka NOMURA、Mitsuko YOSHIOKA、Mitsuo MASAKI、Hiroyuki HARADA、Susumu OKABE

  DOI：10.1248/cpb.40.675

  日期：——

  2-[(2-imidazolylsulfinyl)methyl]anilines (2) having various substituents on their imidazole and aniline rings was synthesized and examined for their H+/K(+)-ATPase (adenosine triphosphatase) inhibitory effects and antisecretory activity against histamine-stimulated gastric acid secretions in Heidenhain pouch dogs. Although substitutions on the imidazole ring did not enhance biological activity, substitutions

  合成了一系列在咪唑和苯胺环上具有各种取代基的2-[（2-咪唑基亚磺酰基）甲基]苯胺（2），并研究了其对H + / K（+）-ATPase（腺苷三磷酸酶）的抑制作用和对分泌的抗分泌活性组胺刺激海登海袋犬的胃酸分泌。尽管在咪唑环上的取代不能增强生物活性，但是通过给电子取代基在苯胺环上的取代可以有效地增强酶的抑制活性，并且在口服后对组胺刺激的胃酸分泌也显示出抑制作用。特别是二甲基（2u--w）和三甲基（2ac）衍生物的体外活性约为奥美拉唑的十倍。另外，4-甲基（2k），4-甲氧基-5-甲基（2y）和3，5-二甲基-4-甲氧基（2ab）衍生物在6 mg / kg口服后显示出超过80％的有效抗分泌作用。尽管这些苯胺衍生物在水溶液中具有相对较低的稳定性，但是用N-（2-甲氧基乙基）基团代替苯胺氮原子上的异丁基基团可以提高稳定性。
• Reaction of 4-bromo-1,2-dimethylbenzene with various nucleophiles via aryne reaction
  作者：Edward R. Biehl、Aziz Razzuk、Misa V. Jovanovic、Subhash P. Khanapure

  DOI：10.1021/jo00376a020

  日期：1986.12
• BIEHL E. R.; RAZZUK A.; JOVANOVIC M. V.; KHANAPURE SUBHASH P., J. ORG. CHEM., 51,(1986) N 26, 5157-5160
  作者：BIEHL E. R.、 RAZZUK A.、 JOVANOVIC M. V.、 KHANAPURE SUBHASH P.

  DOI：——

  日期：——
• One-Pot Reductive Mono-N-alkylation of Aromatic Nitro Compounds Using Nitriles as Alkylating Reagents
  作者：Subhasish Neogi、Dinabandhu Naskar

  DOI：10.1080/00397911.2010.493627

  日期：2011.7.1

  Abstract A one-pot, simple, selective, and efficient protocol for the synthesis of aromatic secondary amines from various nitro arenes and nitriles in the presence of 10% Pd/C catalyst under H2 at atmospheric pressure and ambient temperature in tetrahydrofuran is illustrated. The scope and limitations of this method have been examined.

  摘要 说明了在常压和环境温度下在四氢呋喃中，在 H2 和 10% Pd/C 催化剂存在下，由各种硝基芳烃和腈合成芳香仲胺的一锅法、简单、选择性和高效的方案。已经检查了该方法的范围和局限性。
• Model Systems for Flavoenzyme Activity:  One- and Two-Electron Reduction of Flavins in Aprotic Hydrophobic Environments
  作者：Angelika Niemz、Jason Imbriglio、Vincent M. Rotello

  DOI：10.1021/ja963704a

  日期：1997.2.1

  The processes occurring during the electrochemically irreversible reduction of flavins in aprotic organic medium have been the cause of considerable controversy. To provide insight into these events we have investigated the reduction of flavins alkylated at N(3). We have demonstrated that the reversible reduction of N(3)-methylated flavin can be converted to the irreversible reduction observed with unalkylated flavins through addition of the weak external proton donor phthalimide. Proton transfer to the flavin radical anion generated at the electrode leads to partial formation of the neutral flavin radical; which is instantaneously further reduced to the fully reduced flavin anion. This mirrors the reduction of unalkylated flavins, where the proton source is the imide proton at N(3) of fully oxidized flavin in bulk solution. Simultaneous electrochemistry and EPR experiments confirm the disappearance of electrogenerated flavin radical anion both methylated and non-methylated at N(3), upon addition of phthalimide. UV/vis spectroelectrochemistry likewise confirmed the generation of the radical anion in the absence of proton donors and fully reduced flavin in the presence of proton donors.