3,4-dimethoxy-N-methyl-N-nitrosoaniline

• 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: 3,4-dimethoxy-N-methyl-N-nitrosoaniline
• 英文别名: N-methyl-N-nitroso-3,4-dimethoxyaniline；N-(3,4-dimethoxyphenyl)-N-methylnitrous amide
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: JFDDPDSGAANXLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1Z)-2-偶氮基-1-乙氧基-3-氧代-3-苯基-1-丙烯-1-醇 、 3,4-dimethoxy-N-methyl-N-nitrosoaniline 在 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 、 zinc diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以82%的产率得到
  参考文献：
  名称：

  Co（III）催化芳基CH键与涉及Wolff重排的α-重氮酮的偶联偶联环化

  摘要：

  N-亚硝基苯胺与α-重氮-β-酮酸酯的钴（III）催化的不寻常交叉偶联/环化反应已经实现。该协议具有Csp 2 -H激活/ Wolff重排过程的独特组合，可快速组装四级2-氧吲哚。经验证据和密度泛函理论（DFT）计算揭示了钴金属环对瞬态受体乙烯酮中间体的捕获过程。

  DOI：

  10.1021/acscatal.7b03668
• 作为产物：
  描述：

  3,4-二甲氧基-n-甲基苯胺 在 盐酸 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到3,4-dimethoxy-N-methyl-N-nitrosoaniline
  参考文献：
  名称：

  Structure–Activity Relationship and Rational Design of 3,4-Dephostatin Derivatives as Protein Tyrosine Phosphatase Inhibitors

  摘要：

  Several alkyl- and O-methylated-3,3-dephostatin were synthesized and evaluated for their inhibitory activity toward protein tyrosine phosphatase. Alkyl chains with a length up to that of the pentyl group gave tolerable inhibition, whereas methylation of hydroxyl groups resulted in a decrease in the activity. Based on the structure-activity relationship and X-ray crystallographic analysis of C215S PTP1B-phosphotyrosine containing peptide complex, the mode of binding of 3,4-dephostatins to the active site was speculated with the aid of calculation. Several hydrogen bonds and CH/pi interactions were suggested to be important for inhibition of PTPase. A novel nitroso-free methoxime compound was designed so that all the attractive interactions were maintained. The methoxime compound was synthesized and shown to inhibit PTP1B. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01058-3

文献信息

• 一种3,3-二取代-2-吲哚酮的绿色合成方法
  申请人：海南医学院

  公开号：CN110577483B

  公开（公告）日：2020-05-12

  本发明提供一种3,3‑二取代‑2‑吲哚酮的绿色合成方法，该方法包括以下步骤：在金属盐和碱存在的条件下，以水为溶剂，N‑亚硝基芳胺和乙烯酮在室温条件发生反应，反应完成后，经后处理得到所述的3,3‑二取代‑2‑吲哚酮衍生物。该合成方法主要以水为溶剂，比较绿色环保，同时反应产率较高，反应条件温和，对水和空气都不敏感，操作简便。
• Co(III)-Catalyzed Coupling-Cyclization of Aryl C–H Bonds with α-Diazoketones Involving Wolff Rearrangement
  作者：Xinwei Hu、Xun Chen、Youxiang Shao、Haisheng Xie、Yuanfu Deng、Zhuofeng Ke、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/acscatal.7b03668

  日期：2018.2.2

  cobalt(III)-catalyzed cross-coupling/cyclization of aryl C–H bonds of N-nitrosoanilines with α-diazo-β-ketoesters has been achieved. This protocol features a unique combination of Csp2-H activation/Wolff rearrangement process, allowing for the rapid assembly of quaternary 2-oxindoles. The empirical evidence and density functional theory (DFT) calculations reveal the trapping process of transient acceptor ketene

  N-亚硝基苯胺与α-重氮-β-酮酸酯的钴（III）催化的不寻常交叉偶联/环化反应已经实现。该协议具有Csp 2 -H激活/ Wolff重排过程的独特组合，可快速组装四级2-氧吲哚。经验证据和密度泛函理论（DFT）计算揭示了钴金属环对瞬态受体乙烯酮中间体的捕获过程。
• Structure–Activity Relationship and Rational Design of 3,4-Dephostatin Derivatives as Protein Tyrosine Phosphatase Inhibitors
  作者：Takumi Watanabe、Takayuki Suzuki、Yoji Umezawa、Tomio Takeuchi、Masami Otsuka、Kazuo Umezawa

  DOI：10.1016/s0040-4020(99)01058-3

  日期：2000.1

  Several alkyl- and O-methylated-3,3-dephostatin were synthesized and evaluated for their inhibitory activity toward protein tyrosine phosphatase. Alkyl chains with a length up to that of the pentyl group gave tolerable inhibition, whereas methylation of hydroxyl groups resulted in a decrease in the activity. Based on the structure-activity relationship and X-ray crystallographic analysis of C215S PTP1B-phosphotyrosine containing peptide complex, the mode of binding of 3,4-dephostatins to the active site was speculated with the aid of calculation. Several hydrogen bonds and CH/pi interactions were suggested to be important for inhibition of PTPase. A novel nitroso-free methoxime compound was designed so that all the attractive interactions were maintained. The methoxime compound was synthesized and shown to inhibit PTP1B. (C) 2000 Elsevier Science Ltd. All rights reserved.