1-{[(4-甲基苯基)氨基]氧基}乙酮 | 126875-83-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-{[(4-甲基苯基)氨基]氧基}乙酮
• 中文别名: 噁丙环甲醛,3-苯基-,(2R,3S)-(9CI)
• 英文名称: N-(Acetoxy)toluidin
• 英文别名: N-acetoxy-4-methylaniline；O-acetyl-N-(p-tolyl)hydroxylamine；1-[(4-Methylanilino)oxy]ethan-1-one；(4-methylanilino) acetate
• CAS: 126875-83-0
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: RXHZTWUCCZNGCI-UHFFFAOYSA-N

物化性质

• 沸点：
  235.4±33.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1-{[(4-甲基苯基)氨基]氧基}乙酮 以3%的产率得到
  参考文献：
  名称：

  MEIER, CHRIS;BOCHE, GERNOT, TETRAHEDRON LETT., 31,(1990) N2, C. 1685-1688

  摘要：

  DOI：
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 二氯甲烷-D2 为溶剂， 生成 1-{[(4-甲基苯基)氨基]氧基}乙酮
  参考文献：
  名称：

  Reactions of 2-acylthiazolium salts with N-arylhydroxylamines

  摘要：

  2-Acylthiazolium salts, easily obtained by alkylation of the corresponding 2-acylthiazoles with methyl triflate, react with N-arylhydroxylamines to furnish the O-acyl derivatives of relevance in the induction of cancer by aromatic amines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01161-2

文献信息

• Synthesis, Characterization, and Conformational Analysis of DNA Adducts from Methylated Anilines Present in Tobacco Smoke
  作者：M. Matilde Marques、Luísa L. G. Mourato、M. Amélia Santos、Frederick A. Beland

  DOI：10.1021/tx950044z

  日期：1996.1.1

  to the arylamine nitrogen had a higher percentage of syn conformers. This observation was supported by theoretical simulation studies that indicated substantial percentages of low energy syn conformers, increasing with the substitution pattern in the order para < meta < ortho < ortho,para < ortho,meta. The results demonstrate that, although single-ring arylamines are considered weak carcinogens, their

  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
• A nanostarch functionalized ionic liquid containing imidazolium cation and cobalt chelate anion for the synthesis of carbamates from amines and dimethyl carbonate
  作者：Subodh Kumar、Suman L. Jain

  DOI：10.1039/c3dt52127c

  日期：——

  A new nanostarch functionalized ionic liquid containing imidazolium cation and cobalt chelate anion was synthesized and tested for the one pot synthesis of carbamates by the reaction of amines and dimethyl carbonate (DMC), affording excellent yield of the products under solvent free mild reaction conditions. The synthesized ionic liquid was easily recovered and reused several times without any loss

  合成了一种新的含咪唑鎓阳离子和钴螯合阴离子的纳米淀粉功能化离子液体，并通过胺与碳酸二甲酯（DMC）的反应进行了一次锅法合成氨基甲酸酯的试验，在无溶剂温和的反应条件下提供了优异的收率。合成的离子液体易于回收并重复使用数次，而催化效率没有任何损失。
• Amine organocatalysts for highly <i>ortho</i>-selective chlorination of anilines with sulfuryl chloride
  作者：Xinzhe Wang、Zhihuang Chen、Qingqing Liu、Wenqing Lin、Xiaodong Xiong

  DOI：10.1039/d2cc05320a

  日期：——

  A metal catalyst free approach for regioselective ortho-chlorination of anilines has been developed using a secondary amine as the organocatalyst and sulfuryl chloride as the halogen source under mild conditions. A wide range of substrates were compatible with this catalytic system. In addition, this catalytic protocol has been applied to the efficient synthesis of bioactive compounds and modification

  使用仲胺作为有机催化剂和硫酰氯作为卤素源，在温和条件下开发了一种用于苯胺区域选择性邻氯化的无金属催化剂方法。多种底物与该催化系统相容。此外，该催化方案已应用于生物活性化合物的高效合成和药物衍生物的修饰。进一步的研究表明阴离子三氯化物是邻位选择性的原因。
• Synthesis and Quantification of DNA Adducts of 4,4‘-Methylenedianiline
  作者：Dietrich Schütze、Peter Sagelsdorff、Ovnair Sepai、Gabriele Sabbioni

  DOI：10.1021/tx950194+

  日期：1996.1.1

  4,4'-Methylenedianiline (MDA) is used as a hardener in the manufacture of plastics and polyurethanes. MDA has been classified as a carcinogen in animals and is a suspected human carcinogen. Assuming that MDA would yield similar DNA adducts to other arylamines, we synthesized the following C-8 guanine adducts: N'-acetyl-N-(deoxyguanosin-8-yl)-MDA, N-(deoxyguanosin-8-yl)-MDA, N-(deoxyguanosin-8-yl)-4MA, and their corresponding 3'-monophosphate derivatives. We developed methods to identify these adducts of MDA in liver DNA using P-32-postlabeling, HPLC, and GC-MS techniques. Liver DNA was obtained from rats treated with radiolabeled MDA (1.11 and 116.5 mu mol/kg body weight). The total radioactivity bound to the DNA corresponded to 0.06 and 2.7 adducts per 10(7) nucleotides [covalent binding index (CBI=(mu mol of adduct per mol of nucleotide)/(mmol of compound per kg body weight)) of 1.05 and 2.3]. This DNA-binding potency is in the range of weakly genotoxic compounds. The liver DNA was analyzed for the presence of the synthesized adducts by the following methods: (I) HPLC analysis of nucleotides and purines after enzymatic and acid hydrolysis, and (II) P-32-postlabeling after enzymatic hydrolysis. The major adducts found in vivo did not correspond to the synthesized standards. Further work was carried out to determine the structure of the unidentified adducts. It was possible to release MDA and MDA-d(4) from DNA of rats dosed with MDA and/or MDA-d(4) and from the synthesized adducts using strong base hydrolysis. Liver of two female Wistar rats given 500 mu mol/kg MDA . 2HCl was hydrolyzed in 0.1 M NaOH overnight at 110 degrees C. GC-MS analysis of the heptafluorobutyric anhydride derivatized dichloromethane extracts detected 428+/-40 fmol of MDA/mg of DNA. In the control animals no MDA was found. The experiment was repeated with livers from animals dosed 500 mu mol/kg MDA-d(4) . 2HCl. In these rats 488+/-19 fmol MDA-d(4) was found to be bound at liver DNA. Taking into account a 68% yield of the method, the CBI found in these cases was 0.82 and 1.0, respectively.
• Meier, Chris; Boche, Gernot, Chemische Berichte, 1990, vol. 123, # 8, p. 1699 - 1705
  作者：Meier, Chris、Boche, Gernot

  DOI：——

  日期：——