(4-Methylanilino) 2,2-dimethylpropanoate | 132540-70-6

• 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: (4-Methylanilino) 2,2-dimethylpropanoate
• CAS: 132540-70-6
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: LQEXLEBGILMRBD-UHFFFAOYSA-N

物化性质

• 沸点：
  277.3±33.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-Methylanilino) 2,2-dimethylpropanoate 在 sodium azide 、 三(2-氯乙基)胺 作用下， 以 氘代二甲亚砜 、 重水 为溶剂， 反应 0.5h， 生成 2-azido-4-methylaniline
  参考文献：
  名称：

  Involvement of Free Nitrenium Ions, Ion Pairs, and Preassociation Trapping in the Reactions of Ester Derivatives of N-Arylhydroxylamines and N-Arylhydroxamic Acids in Aqueous Solution

  摘要：

  Rate and product yield data for the decomposition of the ester derivatives of N-arylhydroxylamines and N-arylhydroxamic acids 1a-i in aqueous solution in the presence of N-3(-) support a mechanistic scheme (Scheme 5) in which the trapping by N-3(-) changes from trapping of the free ion, to trapping of an ion pair, to a preassociation process as the ion becomes more reactive. When the rate constant for trapping of the free ion by solvent, k(s), < similar to 10(8) s(-1), trapping by both N-3(-) and solvent occurs almost exclusively at the free ion. When 10(8) s(-1) < similar to k(s) < similar to 10(10) s(-1), a change in the mechanism occurs, and trapping of the ion pair by both solvent and N-3(-) becomes important. In this range of reactivity there is also evidence, based on the apparent magnitude of k(az)', the rate constant for N-3(-) trapping of the ion pair, that some of the reaction with N-3(-) occurs though a preassociation process. When k(s) > similar to 10(10) s(-1) essentially all of the observed N-3(-) trapping occurs by a preassociation process because N-3(-), which cannot react with the ion pair faster than the diffusion limit, can no longer compete with solvent for the ion pair. This progression in trapping mechanisms as the ion becomes more reactive with solvent is apparently an important factor in determining the carcinogenic potential of aromatic amines and amides which are metabolized into sulfuric and carboxylic acid esters of N-arylhydroxylamines and N-arylhydroxamic acids. Nitrenium ions that undergo slow reactions with solvent are selectively trapped by biologically relevant nucleophiles such as 2'-deoxyguanosine, As the rate constant for reaction with solvent increases, the nitrenium ion is no longer capable of undergoing selective trapping by nonsolvent nucleophiles because these reactions are rate limited by diffusion, but solvent trapping is not.

  DOI：

  10.1021/jo00130a034
• 作为产物：
  描述：

  N-(对甲苯基)羟胺 、 特戊酰氰 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (4-Methylanilino) 2,2-dimethylpropanoate
  参考文献：
  名称：

  来自烟草烟雾中甲基化苯胺的DNA加合物的合成，表征和构象分析。

  摘要：

  烟草烟雾中存在的一系列芳香胺（2-，3-和4-甲基苯胺，2,3-和2,4-二甲基苯胺）与DNA结合的能力已通过N-（酰氧基）芳基胺的反应进行了研究带有dG，dG核苷酸和DNA。通过光谱法和HPLC法将与dG和核苷酸反应的主要产物表征为N-（脱氧鸟苷-8-基）芳基胺。修饰DNA的HPLC和光谱分析表明相同的加合物。1 H和13 C NMR光谱的分析表明，含有在芳基胺氮上邻位的甲基取代基的加合物具有较高百分比的顺式构象异构体。这一观察结果得到理论模拟研究的支持，该研究表明低能同构异构体的百分比很高，并且随着取代模式的增加，其对位

  DOI：

  10.1021/tx950044z

文献信息

• Nucleophilic substitution at nitrogen and carboxyl carbon of N-aryl-O-pivaloylhydroxylamines in aqueous solution: competition with SN1 solvolysis of model carcinogens
  作者：John S. Helmick、Michael Novak

  DOI：10.1021/jo00008a064

  日期：1991.4
• Helmick, John S.; Martin, Kristy A.; Heinrich, Julie L., Journal of the American Chemical Society, 1991, vol. 113, # 9, p. 3459 - 3466
  作者：Helmick, John S.、Martin, Kristy A.、Heinrich, Julie L.、Novak, Michael

  DOI：——

  日期：——
• HELMICK, JOHN S.;NOVAK, MICHAEL, J. ORG. CHEM., 56,(1991) N, C. 2925-2927
  作者：HELMICK, JOHN S.、NOVAK, MICHAEL

  DOI：——

  日期：——