1-(m-nitrophenoxy)-2-anilinoethane | 68157-89-1

• 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: 1-(m-nitrophenoxy)-2-anilinoethane
• 英文别名: N-[2-(3-nitro-phenoxy)-ethyl]-aniline；N-[2-(3-Nitrophenoxy)ethyl]aniline
• CAS: 68157-89-1
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: XACSTGHKJXYHMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(m-nitrophenoxy)-2-anilinoethane 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 3-[3-(2-anilinoethoxy)anilino]-4-(1H-indol-3-yl)pyrrole-2,5-dione
  参考文献：
  名称：

  Anilino-monoindolylmaleimides as potent and selective JAK3 inhibitors

  摘要：

  We designed a series of anilino-indoylmaleimides based on structural elements from literature JAK3 inhibitors 3 and 4, and our lead 5. These new compounds were tested as inhibitors of JAKs 1, 2 and 3 and TYK2 for therapeutic intervention in rheumatoid arthritis (RA). Our requirements, based on current scientific rationale for optimum efficacy against RA with reduced side effects, was for potent, mixed JAK1 and 3 inhibition, and selectivity over JAK2. Our efforts yielded a potent JAK3 inhibitor 11d and its eutomer 11e. These compounds were highly selective for inhibition of JAK3 over JAK2 and TYK. The compounds displayed only modest JAK1 inhibition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.001
• 作为产物：
  描述：

  1-(2-溴乙氧基)-3-硝基苯 、 苯胺 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(m-nitrophenoxy)-2-anilinoethane
  参考文献：
  名称：

  Anilino-monoindolylmaleimides as potent and selective JAK3 inhibitors

  摘要：

  We designed a series of anilino-indoylmaleimides based on structural elements from literature JAK3 inhibitors 3 and 4, and our lead 5. These new compounds were tested as inhibitors of JAKs 1, 2 and 3 and TYK2 for therapeutic intervention in rheumatoid arthritis (RA). Our requirements, based on current scientific rationale for optimum efficacy against RA with reduced side effects, was for potent, mixed JAK1 and 3 inhibition, and selectivity over JAK2. Our efforts yielded a potent JAK3 inhibitor 11d and its eutomer 11e. These compounds were highly selective for inhibition of JAK3 over JAK2 and TYK. The compounds displayed only modest JAK1 inhibition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.001

文献信息

• Photoinduced intramolecular substitution-III photocyclization of ω-anilinoalkyl m-nitrophenyl ethers
  作者：Klyoshi Mutai、Keiji Kobayashi、Kenji Yokoyama

  DOI：10.1016/s0040-4020(01)91127-5

  日期：1984.1

  1-(2-methoxy-5-nitrophenoxy) analogs induced intramolecular cyclization in which a hydrogen or methoxyl group at the para position with respect to the nitro group is replaced. Although the replacement of the meta Ar-O bond attached to the polymethylene chain was expected by the analogy with intermolecular photosubstitution, no such product was detected. Several reaction features and laser flash study suggests

  辐射1-（间硝基苯氧基）-ω-苯胺基烷烃，mO 2 NC 6 H 4 O（CH 2）n NHPh（n = 2和3）及其1-（2-甲氧基-5-硝基苯氧基）类似物诱导的分子内环化，其中相对于硝基的对位上的氢或甲氧基被取代。尽管通过与分子间光吸收的类比，预期取代了连接至多亚甲基链的间位Ar-O键，但未检测到这种产物。一些反应特征和激光闪光研究表明，通过光致电子转移机制形成的自由基对在反应的初始阶段参与。
• Magnetic Field Effect as a Probe for Radical Pair Intermediates in the Photoreactions of Nitroaromatic Ethers
  作者：Kiyoshi Mutai、Ryoichi Nakagaki、Hideyuki Tukada

  DOI：10.1246/cl.1987.2261

  日期：1987.11.5

  Intermediacy of a radical ion pair in the photo-Smiles rearrangement of N-[2-(4-nitro-1-naphthoxy)ethyl]aniline in CH3CN was suggested on the basis of magnetic field effects on the photoreaction of its higher homolog.

  N-[2-(4-硝基-1-萘氧基)乙基]苯胺在 CH3CN 中的 photo-Smiles 重排中存在自由基离子对的中介作用，这是基于磁场对其高级同系物光反应的影响。
• PHOTOCYCLIZATION IN 3-[ω-(ANILINO) ALKOXY] NITROBENZENES
  作者：Kiyoshi Mutai、Sei-ichiro Kanno、Keiji Kobayashi

  DOI：10.1246/cl.1978.931

  日期：1978.9.5

  Irradiation of solutions of 3-[ω-(anilino) alkoxy]nitrobenzenes, 3 (n=2 and 3), with 313 nm light gave cyclized products, 5, and 6. No intramolecular substitution at the meta C–O bond was observed. The methylamino analogs, 4, showed only degradation under the same conditions.

  用313 nm的光照射3-[ω-(苯胺基)烷氧基]硝基苯（3）（n=2和3）的溶液，得到环化产物5和6。未观察到间位C-O键的分子内取代反应。甲基氨基类似物4在相同条件下仅出现降解。
• MUTAI, KIYOSHI;KOBAYASHI, KEIJI;YOKOYAMA, KENJI, TETRAHEDRON, 1984, 40, N 10, 1755-1759
  作者：MUTAI, KIYOSHI、KOBAYASHI, KEIJI、YOKOYAMA, KENJI

  DOI：——

  日期：——
• Anilino-monoindolylmaleimides as potent and selective JAK3 inhibitors
  作者：Mark E. McDonnell、Haiyan Bian、Jay Wrobel、Garry R. Smith、Shuguang Liang、Haiching Ma、Allen B. Reitz

  DOI：10.1016/j.bmcl.2014.01.001

  日期：2014.2

  We designed a series of anilino-indoylmaleimides based on structural elements from literature JAK3 inhibitors 3 and 4, and our lead 5. These new compounds were tested as inhibitors of JAKs 1, 2 and 3 and TYK2 for therapeutic intervention in rheumatoid arthritis (RA). Our requirements, based on current scientific rationale for optimum efficacy against RA with reduced side effects, was for potent, mixed JAK1 and 3 inhibition, and selectivity over JAK2. Our efforts yielded a potent JAK3 inhibitor 11d and its eutomer 11e. These compounds were highly selective for inhibition of JAK3 over JAK2 and TYK. The compounds displayed only modest JAK1 inhibition. (C) 2014 Elsevier Ltd. All rights reserved.