2-(pentyloxy)aniline | 52464-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(pentyloxy)aniline
• 英文别名: 2-pentyloxyaniline；2-pentyloxy-aniline；2-Pentyloxy-anilin；Benzenamine, 2-(pentyloxy)-；2-pentoxyaniline
• CAS: 52464-51-4
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: IOEQZAIBXFYINW-UHFFFAOYSA-N

物化性质

• 沸点：
  143-144 °C(Press: 19 Torr)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(pentyloxy)aniline 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 二苯醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 N-(adamantan-1-yl)-4-oxo-8-(pentyloxy)-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 4. Identification of New Potent and Selective Ligands for the Cannabinoid Type 2 Receptor with Diverse Substitution Patterns and Antihyperalgesic Effects in Mice

  摘要：

  Experimental evidence suggests that selective CB2 receptor modulators may provide access to antihyperalgesic agents devoid of psychotropic effects. Talcing advantage of previous findings on structure-activity/selectivity relationships for a class of 4-quinolone-3-carboxamides, further structural modifications of the heterocyclic scaffold were explored, leading to the discovery of the 8-methoxy derivative 4a endowed with the highest affinity and selectivity ever reported for a CB2 ligand. The compound, evaluated in vivo in the formalin test, behaved as an inverse agonist by reducing at a dose of 6 mg/kg the second phase of the formalin-induced nocifensive response in mice.

  DOI：

  10.1021/jm200476p
• 作为产物：
  描述：

  1-碘戊烷 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 22.0h， 生成 2-(pentyloxy)aniline
  参考文献：
  名称：

  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 4. Identification of New Potent and Selective Ligands for the Cannabinoid Type 2 Receptor with Diverse Substitution Patterns and Antihyperalgesic Effects in Mice

  摘要：

  Experimental evidence suggests that selective CB2 receptor modulators may provide access to antihyperalgesic agents devoid of psychotropic effects. Talcing advantage of previous findings on structure-activity/selectivity relationships for a class of 4-quinolone-3-carboxamides, further structural modifications of the heterocyclic scaffold were explored, leading to the discovery of the 8-methoxy derivative 4a endowed with the highest affinity and selectivity ever reported for a CB2 ligand. The compound, evaluated in vivo in the formalin test, behaved as an inverse agonist by reducing at a dose of 6 mg/kg the second phase of the formalin-induced nocifensive response in mice.

  DOI：

  10.1021/jm200476p

文献信息

• Studies on antiallergy agents. III. Synthesis of 2-anilino-1,6-dihydro-6-oxo-5-pyrimidinecarboxylic acids and related compounds.
  作者：Kohji OZEKI、Teru ICHIKAWA、Hiroyuki TAKEHARA、Kenjiro TANIMURA、Makoto SATO、Hideya YAGINUMA

  DOI：10.1248/cpb.37.1780

  日期：——

  A series of 2-anilino-1,6-dihydro-6-oxo-5-pyrimidinecarboxylic acids with various substituents was synthesized and evaluated in the rat passive cutaneous anaphylaxis test for antiallergic activity. High activity by intraperitoneal and oral administrations was observed for the 3-trifluoromethyl and 2-alkoxyanilino derivatives (64, 79, 81, 82 and 85). Structure-activity relationships are discussed.

  合成了一系列具有各种取代基的2-苯胺基-1,6-二氢-6-氧代-5-嘧啶羧酸，并在大鼠被动皮肤过敏反应试验中评估了其抗过敏活性。对于3-三氟甲基和2-烷氧基苯胺基衍生物（64、79、81、82和85），观察到腹膜内和口服给药具有高活性。讨论了构效关系。
• Selective alkylation of aminophenols
  作者：Jiaxi Xu、Renchao Wang

  DOI：10.3998/ark.5550190.0011.927

  日期：——

  Oor N-Alkylated derivatives of aminophenols are important synthetic intermediates in organic synthesis. A series of aminophenols were selectively alkylated on their hydroxyl group in good yields via benzaldehyde protection of the amino group, subsequent alkylation, and hydrolysis; or on their amino group via imination and following reduction.

  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。
• Determination of Critical Micellar Concentration of Homologous 2-Alkoxyphenylcarbamoyloxyethyl-Morpholinium Chlorides
  作者：Lenka Stopková、Jana Gališinová、Zuzana Šuchtová、Jozef Čižmárik、Fils Andriamainty

  DOI：10.3390/molecules23051064

  日期：——

  The critical micellar concentrations of selected alkyloxy homologues of local anesthetic 4-(2-[(2-alkoxyphenyl)carbamoyl]oxy}ethyl)morpholin-4-ium chloride with nc = 2, 4, 5, 6, 7, 8, and 9 carbons in alkyloxy tail were determined by absorption spectroscopy in the UV–vis spectral region with the use of a pyrene probe. Within the homologous series of the studied amphiphilic compounds, the ln(cmc) was

  局部麻醉剂 4-(2-[(2-alkoxyphenyl)carbamoyl]oxy}ethyl)morpholin-4-ium 氯化物的选定烷氧基同系物的临界胶束浓度，nc = 2, 4, 5, 6, 7, 8,烷氧基尾中的 9 个碳原子是通过使用芘探针在紫外-可见光谱区的吸收光谱测定的。在研究的两亲化合物的同源系列中，观察到 ln(cmc) 与疏水尾中的碳原子数 nc 线性相关：ln(cmc) = 0.705–0.966 nc。发现在 25 °C 和 pH ≈ 4.5–5.0 的温度下，烷氧基链的亚甲基从水相转移到胶束内部所必需的吉布斯自由能为 -2.39 kJ/摩尔。
• Dibasic Derivatives of Phenylcarbamic Acid Against Mycobacterial Strains: Old Drugs and New Tricks?
  作者：Ivan Malík、Jozef Csöllei、Ivan Solovič、Šárka Pospíšilová、Hana Michnová、Josef Jampílek、Alois Čížek、Iva Kapustíková、Jana Čurillová、Mária Pecháčová、Jiřina Stolaříková、Daniel Pecher、Michal Oravec

  DOI：10.3390/molecules23102493

  日期：——

  provide a more detailed view on the structure⁻antimycobacterial activity relationship (SAR) of phenylcarbamic acid derivatives containing two centers of protonation, 1-[2-[([2-/3-(alkoxy)phenyl]amino}carbonyl)oxy]-3-(dipropylammonio)propyl]pyrrolidinium oxalates (1a⁻d)/dichlorides (1e⁻h) as well as 1-[2-[([2-/3-(alkoxy)phenyl]amino}carbonyl)oxy]-3-(di-propylammonio)propyl]azepanium oxalates (1i⁻l)/dichlorides

  研究了实验log kw数据集，以及主要基于原子或原子与碎片结合原理通过各种方法生成的分配系数的计算对数（log P）。通过非标度主成分分析（PCA）分析了实验性和计算机模拟的亲脂性描述子之间的异同。检查化合物1a⁻p的体外活性是否与结核分枝杆菌CNCTC My 331/88（分别与H37Rv和ATCC 2794相同），结核分枝杆菌H37Ra ATCC 25177，堪萨斯分枝杆菌CNCTC My 235/80（与ATCC 12478相同） ），堪萨斯分枝杆菌6509/96临床分离株，堪萨斯分枝杆菌DSM 44162，鸟分枝杆菌CNCTC My 330/80（与ATCC 25291相同），耻垢分枝杆菌ATCC 700084和海藻分枝杆菌CAMP 5644。还测试了分枝杆菌对参考药物异烟肼，乙胺丁醇，氧氟沙星或环丙沙星的体外敏感性。该研究的一个非常独特的方面是，来自1a⁻p的许多化合物几乎对所有
• Aryl carbonyl derivatives as therapeutic agents
  申请人：——

  公开号：US20040122235A1

  公开（公告）日：2004-06-24

  This invention relates to aryl carbonyl derivatives which are activators of glucokinase which may be useful for the management, treatment, control, or adjunct treatment of diseases, where increasing glucokinase activity is beneficial.

  本发明涉及芳基羰基衍生物，其是葡萄糖激酶的激活剂，可用于管理、治疗、控制或辅助治疗增加葡萄糖激酶活性有益的疾病。