2-(5-羟基-1-戊炔-1-基)苯胺 | 380415-68-9

• 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: 2-(5-羟基-1-戊炔-1-基)苯胺
• 英文名称: 2-(5-hydroxy-1-pentyn-1-yl)aniline
• 英文别名: 2-(5-hydroxypent-1-ynyl)aniline；5-(2-aminophenyl)pent-4-yn-1-ol
• CAS: 380415-68-9
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: QYFMVNPOIHDQBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-羟基-1-戊炔-1-基)苯胺 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 C₃₁H₄₉P₃ 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 methyl (E)-3-(1-(2-acetamidophenyl)-5-hydroxypent-1-en-2-yl)-2-cyclopropyl-1-tosyl-1H-indole-5-carboxylate
  参考文献：
  名称：

  Rhodium-Catalyzed Selective Nucleophilic Cyclization/Cross-Coupling of Two ortho-Alkynylanilines Bearing Differential N-Substituents

  摘要：

  DOI：

  10.1021/acs.orglett.3c02180
• 作为产物：
  描述：

  4-戊炔-1-醇 、 2-碘苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 以99%的产率得到2-(5-羟基-1-戊炔-1-基)苯胺
  参考文献：
  名称：

  抗真菌环肽Rhopepteptin的新型拟肽：模拟物的合成及其抗真菌活性。

  摘要：

  [反应：请参见文字]。合成了新型的抗真菌环肽Rhodopeptin拟肽。与环状肽一样，发现所有三个杜鹃肽侧链的存在对于拟肽活性都是必不可少的。我们发现与母体化合物相比，新化合物表现出更大的抗真菌活性和改善的理化特性。

  DOI：

  10.1021/ol016394w

文献信息

• Sc(OTf)₃-Catalyzed Bicyclization of<i>o</i>-Alkynylanilines with Aldehydes: Ring-Fused 1,2-Dihydroquinolines
  作者：Can Zhu、Shengming Ma

  DOI：10.1002/anie.201406959

  日期：2014.12.1

  A Sc(OTf)3‐catalyzed cascade Prins‐type cyclization reaction of o‐alkynylanilines, bearing a hydroxy or amine functionality, with aldehydes affords 1,2‐dihydroquinoline derivatives having an extra fused ring efficiently under mild reaction conditions. It is interesting to observe the reversed reactivity in the highly selective formation of 1,2‐dihydroquinoline derivatives instead of the formation of

  带有羟基或胺官能团的邻炔基苯胺的Sc（OTf）3催化级联Prins型环化反应与醛可在温和的反应条件下有效地提供具有额外稠合环的1,2-二氢喹啉衍生物。有趣的是，在高选择性地形成1,2-二氢喹啉衍生物而不是通常偏爱的吲哚衍生物的过程中观察到逆反应性。
• Tandem cyclization of <i>o</i>-alkynylanilines with isocyanides triggered by intramolecular nucleopalladation: access to heterocyclic fused 2-aminoquinolines
  作者：Wanqing Wu、Meng Li、Jia Zheng、Weigao Hu、Chunsheng Li、Huanfeng Jiang

  DOI：10.1039/c8cc02028k

  日期：——

  Herein, a novel strategy for the synthesis of various heterocyclic fused 2-aminoquinolines via palladium-catalyzed tandem cyclization of o-alkynylanilines with isocyanides has been developed. This process includes trans-oxy/aminopalladation, isocyanide insertion, elimination and 1,3-hydrogen migration. Besides high atom and step economy, this method shows good functional group compatibility with excellent

  在本文中，已经开发了一种新的策略，该策略通过钯催化的邻炔基苯胺与异氰化物的串联环合反应来合成各种杂环稠合的2-氨基喹啉。该过程包括反式-氧/氨基palpalpalation，异氰酸酯插入，消除和1,3-氢迁移。该方法除具有较高的原子和步骤经济性外，在温和的反应条件下，还具有良好的官能团相容性以及出色的化学和区域选择性。
• Catalyzed Tandem C–N/C–C Bond Formation for the Synthesis of Tricyclic Indoles using Ir(III) Pyrazolyl-1,2,3-Triazolyl Complexes
  作者：Chin Min Wong、Khuong Q. Vuong、Mark R. D. Gatus、Carol Hua、Mohan Bhadbhade、Barbara A. Messerle

  DOI：10.1021/om300792b

  日期：2012.11.12

  C–C bond formation step. The C–N bond formation leading to the formation of indoles was found to proceed via two reaction pathways with 2-(hydroxyalk-1-ynyl)aniline substrates: (a) hydroamination and (b) hydroalkoxylation–Lewis acid mediated isomerization. Pathway (b) is likely to be the main pathway in the formation of indoles starting with 2-(hydroxyalk-1-ynyl)aniline substrates 17S, 18S, and 20S.

  通过Cu（I）催化的1-炔丙基吡唑与4-取代的苯基之间的惠斯根环加成反应，制备了一系列新的吡唑基-1,2,3-三唑基N - N'双齿供体配体（2a - c，3a - d）叠氮化物。取代基的吸电子能力遵循趋势PhCH 2 < p -CH 3 Ph 1000 h –1。然而，铱（III）配合物5 - 8被发现是用于串联C-N和C-C键形成的唯一的活性催化剂，因为铑（I）配合物是不为C-C键形成的活性催化剂步。发现导致吲哚形成的C–N键的形成是通过与2-（羟基烷基-1-炔基）苯胺底物的两个反应途径进行的：（a）加氢胺化和（b）加氢烷氧基化-路易斯酸介导的异构化。途径（b）可能是从2-（羟基烷-1-炔基）苯胺底物17S，18S和20S开始形成吲哚的主要途径。
• Direct Electrooxidative Selenylamination of Alkynes: Access to 3‐Selenylindoles
  作者：Balati Hasimujiang、Yong Zeng、Shifeng Zou、Kaihui Zhong、Lebin Su、Xinwei Hu、Zhixiong Ruan

  DOI：10.1002/ijch.202300088

  日期：2024.1

  A novel metal‐ and oxidant‐free electrooxidative selenylamination of o‐aminophenacetylenes with diselenides for achieving 3‐selenylindoles has been developed with moderate to excellent yield. The reaction proceeded smoothly with a broad substrate scope and highly functional group tolerance. The synthetic practicality of this innovative approach was demonstrated by its easy scalability. Moreover, mechanistic studies revealed that an in‐situ generated selenium cation might be the key intermediate for the electrochemical selenocyclization process.

  摘要 研究人员开发了一种新型的无金属和氧化剂的邻氨基苯乙炔与二硒化物的电氧化硒化反应，以获得 3-硒基吲哚，该反应具有中等到极好的收率。反应进行顺利，底物范围广，官能团耐受性高。这种创新方法的易扩展性证明了其合成的实用性。此外，机理研究表明，原位生成的硒阳离子可能是电化学硒环化过程的关键中间体。
• Discovery, Synthetic Methodology, and Biological Evaluation for Antiphotoaging Activity of Bicyclic[1,2,3]triazoles: In Vitro and in Vivo Studies
  作者：Hsin-Yu Hsieh、Wen-Chun Lee、Gopal Chandru Senadi、Wan-Ping Hu、Jium-Jia Liang、Tong-Rong Tsai、Yu-Wei Chou、Kung-Kai Kuo、Chung-Yu Chen、Jeh-Jeng Wang

  DOI：10.1021/jm400394s

  日期：2013.7.11

  Novel bicyclic[1,2,3]triazoles (4, 7, 11, 15) have been synthesized using a one-pot metal free strategy with high structural diversity as photoprotective agents, and their effect on UVA-induced senescence in human dermal fibroblast cells (FB) and the associated mechanism are delineated. lid plus UVA can induce a decrease in reactive oxygen species (ROS) production and senescence-associated beta-galactosiclase (SA-beta-gal) activity but an increase in adenosine triphosphate (ATP) synthesis and mitochondrial membrane potential (Delta psi(mt)). The mRNA levels of six senescence-associated genes, matrix metalloproteinase-1 (MMP-1), was decreased, while elastin, procollagen I type I, fibronectin, COL1 alpha 1, and tissue inhibitor of metalloproteinase-1 (TIMP-1) were increased. lid plus UVA also decreased MMP-1 and increased TIMP-1 protein levels. Additionally, the thickness of the minim dorsal skin and epidermis, by UVA, was decreased by topical lid treatment. Our results indicate that bicyclic[1,2,3]triazoles protect UVA-induced senescence-like characteristics in FB cells, which may provide potential prevention against photoaging.