2-(but-2-yloxy)aniline | 52464-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(but-2-yloxy)aniline
• 英文别名: 2-sec-butoxyaniline；2-sec-butoxy-phenylamine；o-sec-butoxyaniline；(2-Sec-butoxyphenyl)amine；2-butan-2-yloxyaniline
• CAS: 52464-53-6
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: RDWZXAYXEUNBBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  2-(but-2-yloxy)aniline 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.17h， 生成 1-(2-sec-Butoxy-phenyl)-3-((1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-urea
  参考文献：
  名称：

  5-Hydroxytryptamine (5-HT3) receptor antagonists. 3. Ortho-substituted phenylureas

  摘要：

  A novel series of potent 5-HT3 receptor antagonists, ortho-substituted phenylureas 6a-z, is described in which the 5-membered ring of the previously reported indazoles and indolines has been replaced by an intramolecular hydrogen bond. High potency was found both for carbamate 6a and urea 6b. Granatane 6c was less potent than the equivalent tropane. Phenylurea 11c lacking the ortho substituent was inactive. Whereas further substitution could not be tolerated in the aromatic ring, activity was retained with a range of O-alkyl groups, compounds 6k-t. In addition, good activity was found for ortho ester 6u and sulfonamide 6x. The ortho-substituted phenylureas can therefore be regarded as bioisosteres of the 6,5-heterocycles indole, indazole, and indoline.

  DOI：

  10.1021/jm00169a018
• 作为产物：
  描述：

  2-碘丁烷 、 2-(苯基亚甲基氨基)苯酚 在 potassium carbonate 、 盐酸 作用下， 以 丙酮 、 二氯甲烷 、 水 为溶剂， 反应 21.0h， 以31.5%的产率得到2-(but-2-yloxy)aniline
  参考文献：
  名称：

  氨基酚的选择性烷基化

  摘要：

  氨基苯酚的O或N-烷基化衍生物是有机合成中重要的合成中间体。通过氨基苯甲醛保护，随后烷基化和水解，一系列氨基酚在其羟基上以良好的收率被选择性烷基化；或通过亚胺化和随后的还原作用在其氨基上。

  DOI：

  10.3998/ark.5550190.0011.927

文献信息

• [EN] METHOD FOR PRODUCING 1-HEXENE<br/>[FR] PROCÉDÉ DE PRODUCTION D'1-HEXÈNE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2012133937A1

  公开（公告）日：2012-10-04

  Disclosed is a method for producing 1-hexene that is capable of reducing the amount of by-product polymers when 1-hexene is produced through the trimerization reaction of ethylene. The method for producing 1-hexene comprises the following steps 1 and 2: step 1: the step of preparing a catalytic component by bringing a transition metal complex represented by any one of formulae (1-1) to (1-3) into contact with a specific organic aluminum compound in the absence of ethylene; and step 2: the step of trimerizing ethylene in the presence of a catalyst obtainable by bringing the catalytic component obtained in step 1 into contact with a specific boron compound.

  公开了一种生产1-己烯的方法，该方法能够在通过乙烯的三聚反应生产1-己烯时减少副产物聚合物的数量。生产1-己烯的方法包括以下步骤1和2：步骤1：通过将由式（1-1）到（1-3）中的任一表示的过渡金属配合物与特定有机铝化合物接触而制备催化组分，在没有乙烯的情况下；步骤2：在将在步骤1中获得的催化组分与特定硼化合物接触而获得的催化剂存在下，三聚乙烯。
• [EN] METHOD FOR PRODUCING THE TRANSITION METAL ION COMPLEX, CATALYST FOR TRIMERIZATION, AND METHOD FOR PRODUCING 1-HEXENE<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN COMPLEXE ION MÉTAL DE TRANSITION, CATALYSEUR DE TRIMÉRISATION, ET PROCÉDÉ DE PRODUCTION DE 1-HEXÈNE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2012133929A1

  公开（公告）日：2012-10-04

  An object of the present invention is to provide a silicon-bridged Cp-Ar transition metal complex that serves as a catalytic component capable of efficiently and highly selectively producing 1-hexene through the trimerization reaction of ethylene. The present invention provides a transition metal ion complex represented by any of formulae (1-1) to (1-3), etc.: wherein M represents a transition metal atom of Group 4 of the Periodic Table of the Elements; A represents a counter anion; R1, R2, R3, R4, R5, R6, R7, R8, R9, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, X1 and X2 each independently represent a hydrogen atom or the like; R10 and R11 each independently represent a hydrogen atom or the like.

  本发明的一个目的是提供一种硅桥联的Cp-Ar过渡金属配合物，作为一种催化组分，能够通过乙烯三聚反应高效且高选择性地产生1-己烯。本发明提供了一种过渡金属离子配合物，其表示为任一化学式（1-1）至（1-3）等：其中M表示元素周期表第4族的过渡金属原子；A表示反离子；R1、R2、R3、R4、R5、R6、R7、R8、R9、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、X1和X2每个独立地表示氢原子或类似物；R10和R11每个独立地表示氢原子或类似物。
• Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides
  作者：Tomas Gonec、Iveta Zadrazilova、Eoghan Nevin、Tereza Kauerova、Matus Pesko、Jiri Kos、Michal Oravec、Peter Kollar、Aidan Coffey、Jim O'Mahony、Alois Cizek、Katarina Kralova、Josef Jampilek

  DOI：10.3390/molecules20069767

  日期：——

  A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 µM against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 µM and 24 µM against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 µM) was the most active PET inhibitor. The structure-activity relationships are discussed.

  制备并表征了一系列15种新的N-烷氧基苯基苯胺衍生物，针对3-羟基萘-2-羧酸。对合成化合物进行的初步体外筛选涉及金黄色葡萄球菌、三种耐甲氧西林金黄色葡萄球菌株、结核分枝杆菌H37Ra和副结核分枝杆菌。部分测试化合物显示出对所测试菌株的抗菌和抗分枝杆菌活性，与标准药物青霉素或利福平相当或更强。3-羟基-N-(2-丙氧基苯基)萘-2-羧酰胺和N-[2-(丁-2-氧基)苯基]-3-羟基萘-2-羧酰胺对所有耐甲氧西林金黄色葡萄球菌株的最低抑制浓度为12 µM，因此它们的活性是青霉素的4倍。第二种提到的化合物以及3-羟基-N-[3-(丙-2-氧基)苯基]-萘-2-羧酰胺对结核分枝杆菌的最低抑制浓度分别为23 µM和24 µM。N-[2-(丁-2-氧基)苯基]-3-羟基萘-2-羧酰胺对副结核分枝杆菌显示出比利福平更高的活性。使用THP-1细胞对最有效的抗分枝杆菌化合物进行的细胞毒性筛选中，观察到大多数有效化合物未表现出显著的致死效应。此外，这些化合物还被测试了其对菠菜(Spinacia oleracea L.) 叶绿体中光合电子传递(PET)的抑制活性。N-(3-乙氧基苯基)-3-羟基萘-2-羧酰胺(半数抑制浓度 = 4.5 µM)是最活跃的PET抑制剂。讨论了结构-活性关系。
• Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides †
  作者：Iva Kapustikova、Andrzej Bak、Tomas Gonec、Jiri Kos、Violetta Kozik、Josef Jampilek

  DOI：10.3390/molecules23071635

  日期：——

  series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity

  对于ADMET量身定制的结构活性模型的合理设计，评估生物活性剂的亲脂特性是必不可少的。N-烷氧基-3-羟基萘-2-甲酰苯胺，N-烷氧基-1-羟基萘-2-甲酰苯胺和N-烷氧基-2-羟基萘-1-甲酰苯胺最近被报道为一系列具有抗分枝杆菌，抗菌素和除草活性。由于发现这些生物活性剂的亲脂性决定了它们的活性，因此在本研究中对这三个系列的亲脂性进行了研究。使用反相高效液相色谱法分析所有57种苯胺类化合物的亲脂性。该过程是在等度条件下，使用封端的非极性C18固定反相色谱柱在甲醇中作为流动相的有机改性剂进行的。在本研究中，使用了一系列亲脂性预测软件来估算一组N-烷氧基苯基羟基萘甲酰胺的clogP值，随后与实验参数进行了交叉比较。因此，将亲脂性（logk）和分布参数（π）的经验值与使用推论亲脂性特征的替代方法计算出的相应计算机特性进行了比较。为了研究衍生物之间的（不相似）相似性，采用了PCA程序以可视化方式观察分子在亲脂性方面的主要性能差异，
• N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity
  作者：Tomas Gonec、Sarka Pospisilova、Tereza Kauerova、Jiri Kos、Jana Dohanosova、Michal Oravec、Peter Kollar、Aidan Coffey、Tibor Liptaj、Alois Cizek、Josef Jampilek

  DOI：10.3390/molecules21081068

  日期：——

  compounds showed antimycobacterial activity comparable with or higher than that of rifampicin. For example, 2-hydroxy-N-(4-propoxyphenyl)-naphthalene-1-carboxamide showed the highest activity (MIC = 12 µM) against M. tuberculosis with insignificant cytotoxicity. N-[3-(But-2-yloxy)phenyl]- and N-[4-(but-2-yloxy)phenyl]-2-hydroxy-naphthalene-1-carboxamide demonstrated high activity against all tested

  制备并表征了一系列十九个 N-(烷氧基苯基)-2-羟基萘-1-甲酰胺及其十九个位置异构体 N-(烷氧基苯基)-1-羟基萘-2-甲酰胺。针对结核分枝杆菌 H37Ra、堪萨斯分枝杆菌和耻垢分枝杆菌对所有合成化合物进行初步体外筛选。使用人单核细胞白血病THP-1细胞对化合物的细胞毒性进行筛选。一些测试化合物显示出与利福平相当或高于利福平的抗分枝杆菌活性。例如，2-羟基-N-(4-丙氧基苯基)-naphthalene-1-carboxamide 对结核分枝杆菌的活性最高 (MIC = 12 µM)，细胞毒性不明显。N-[3-(But-2-yloxy)phenyl]- 和 N-[4-(but-2-yloxy)phenyl]-2-hydroxy-naphthalene-1-carboxamide 对所有测试的分枝杆菌菌株表现出很高的活性，并且不显着细胞毒性。N-(烷氧基苯基)-1-羟基萘-2-甲酰胺对