(1-methylbutyl)phenylamine | 2716-62-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1-methylbutyl)phenylamine
• 英文别名: N-(pentan-2-yl)aniline；N-2-pentylaniline；N-(1-methyl-butyl)-aniline；N-(1-Methyl-butyl)-anilin；N-(1-methylbutyl)-benzenamine；N-(1-methylbutyl)aniline；N-pentan-2-ylaniline
• CAS: 2716-62-3
• 化学式: C₁₁H₁₇N
• 分子量: 163.263
• InChiKey: HULIKQJHXKLBMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1-methylbutyl)phenylamine 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Higher-Affinity Agonists of 5-HT_1AR Discovered through Tuning the Binding-Site Flexibility

  摘要：

  Discovery of high-affinity and high-selectivity agonists of 5-HT1AR. has become very attractive due to their potential therapeutic effects on multiple 5-HT1AR-related psychological and neurological problems. On the basis of our previously designed lead compound FW01 (K-i = 51.9 nM, denoted as 9a in the present study), we performed large-scale molecular dynamics simulations and molecular docking operations on 5-HT1AR-9a binding. We found the flip-packing events for the headgroup of 9a, and we also found that its tail group could bind flexibly at the agornst-binding site of 5-HT1AR. By finely tuning the flip-packing phenomenon of the 9a headgroup and tuning the binding flexibility of 9a tail group, we virtually designed a series of new 9a derivatives through molecular docking operations and first-principles calculations and predicted that these newly designed 9a derivatives should be higher-affinity agonists of 5-HT1AR. The computational predictions on the new 9a derivatives have been confirmed by our wet-experimental studies as chemical synthesis, binding affinity assays, and agonistic-function assays. The consistency between our computational design and wet-experimental measurements has led to our discovery of higher-affinity agonists of 5-HT1AR, with,similar to 50-fold increase in receptor-binding affinity and similar to 25-fold improvements in agonistic function. In addition, our newly designed 5-HT1AR agonists showed very high selectivity of 5-HT1AR over subtype 5-HT2AR and also over three subtypes of dopamine receptors (D-1, D-2, and D-3).

  DOI：

  10.1021/acs.jcim.5b00164
• 作为产物：
  描述：

  苯胺 以 丙酮 为溶剂， 生成 (1-methylbutyl)phenylamine
  参考文献：
  名称：

  Blue to green disperse dyes for synthetic fiber material

  摘要：

  一种化学式（1）的染料：##STR1## 其中：D是化学式（2）的基团：##STR2## 或化学式（3）的基团：##STR3## 或化学式（4）的基团：##STR4## 变量在披露中有定义。这些染料和染料混合物可在合成纺织材料（如聚酯）上产生蓝色到绿色的色调，具有良好的建立和良好的耐光和耐湿性。

  公开号：

  US05865857A1

文献信息

• [EN] NOVEL N-SUBSTITUTED DIHYDROBENZOTHIEPINO, DIHYDROBENZOXEPINO AND TETRAHYDRO BENZOCYCLOHEPTA INDOLES AS SELECTIVE ESTROGEN RECEPTOR MODULATORS<br/>[FR] NOUVEAUX DIHYDROBENZOTHIEPINO, DIHYDROBENZOXEPINO ET TETRAHYDRO BENZOCYCLOHEPTA INDOLES N-SUBSTITUES UTILISES EN TANT QUE MODULATEURS DU RECEPTEUR DES OESTROGENES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2005094833A1

  公开（公告）日：2005-10-13

  The invention provides a novel class of N-substituted dihydrobenzothiepino, dihydrobenzoxepino and tetrahydro benzocyclohepta indoles of Formula (I) and their pharmaceutically acceptable salts, and methods for of synthesizing these compounds. The invention further comprises pharmaceutical compositions and methods of use for these compounds for the treatment of estrogen related diseases or disorders.

  这项发明提供了一类新型的Formula (I)的N-取代二氢苯并噻吩、二氢苯并氧吩和四氢苯并环庚哌啉以及它们的药用盐，以及合成这些化合物的方法。该发明还包括用于治疗雌激素相关疾病或紊乱的这些化合物的药用组合物和使用方法。
• Facile and efficient reductive N-alkylation of nitrobenzenes with alcohols catalyzed by Cu–Cr/γ-Al2O3
  作者：Ge Song、Jun Tian、Ligong Chen、Yang Li

  DOI：10.1007/s11164-014-1641-6

  日期：2015.8

  A facile and efficient method for reductive N-alkylation of nitrobenzenes with alcohols catalyzed by the bimetallic catalyst Cu30Cr5/γ-Al2O3, in a fixed-bed reactor, was successfully established. X-ray diffraction, temperature-programmed reduction, and X-ray photoelectron spectroscopy were used to characterize the catalyst. Introduction of Cr to Cu30/γ-Al2O3 was found to substantially enhance the dispersion of Cu0 particles, which are believed to be the active sites for the reductive N-alkylation. The reaction conditions were optimized and a series of alcohols and nitrobenzenes were converted into N-alkylated anilines in more than 90 % yield by use of this catalyst.

  成功建立了一种简便高效的方法，通过双金属催化剂Cu30Cr5/γ-Al2O3在固定床反应器中，用醇还原烷基化亚硝基苯。采用X射线衍射、温度程序还原和X射线光电子能谱对催化剂进行了表征。研究发现，将Cr引入Cu30/γ-Al2O3显著增强了Cu0颗粒的分散性，而Cu0颗粒被认为是还原烷基化反应的活性位点。对反应条件进行了优化，使用该催化剂将一系列醇和亚硝基苯转化为N-烷基化的苯胺，产率超过90%。
• Direct Catalytic Asymmetric Reductive Amination of Aliphatic Ketones Utilizing Diphenylmethanamine as Coupling Partner
  作者：Haizhou Huang、Yunfei Zhao、Yang Yang、Le Zhou、Mingxin Chang

  DOI：10.1021/acs.orglett.7b00212

  日期：2017.4.21

  The highly efficient direct catalytic reductive amination of ketones with diphenylmethanamine catalyzed by iridium–phosphoramidite complexes is described. As an effective coupling partner, diphenylmethanamine is suitable for a wide range of ketones to provide chiral amines in high yields and enantioselectivity. The chiral monodentate phosphoramidite ligands are tunable and competent to accommodate

  描述了铱-亚磷酰胺配合物催化的二苯甲胺对酮的高效直接催化还原胺化反应。作为有效的偶合伴侣，二苯基甲胺适用于多种酮，以高收率和对映选择性提供手性胺。手性单齿亚磷酰胺配体是可调的，并且能够容纳具有不同结构的底物。
• Design, Synthesis, and Structure–Activity Relationship Studies of Novel Indolyalkylpiperazine Derivatives as Selective 5-HT_1A Receptor Agonists
  作者：Wenli Wang、Lan Zheng、Wei Li、Chen Zhu、Weiqing Peng、Bing Han、Wei Fu

  DOI：10.1021/acs.jcim.9b00926

  日期：2020.1.27

  5-HT1A receptor (5-HT1AR) agonists have been implicated in the treatment of a variety of central nervous system (CNS) diseases such as depression and anxiety, et al. Based on our previously found compound FW01 (Ki = 51 ± 16 nM) obtained by virtual screening, a series of FW01 derivatives were designed and synthesized by the modification of the amide tail group as well as indole headgroup of FW01. SAR

  5-HT1A受体（5-HT1AR）激动剂已涉及多种中枢神经系统（CNS）疾病的治疗，例如抑郁症和焦虑症等。基于我们先前发现的通过虚拟筛选获得的化合物FW01（Ki = 51±16 nM），通过修饰FW01的酰胺尾基和吲哚基团设计并合成了一系列FW01衍生物。SAR探索发现，酰胺尾基和吲哚基团在确定对多巴胺和5-羟色胺受体亚型的结合亲和力和选择性中起着关键作用。在所有测试的化合物中，9_24的Ki值为5±0.6 nM，对5-HT1AR的选择性很好。[35S]GTPγS分析显示9_24是对5-HT1AR的完全激动剂，EC50值为0.059 nM，显示为266.2和146。对5-HT2A和D3的选择性是4倍。用5-HT1AR-9_24进行了分子动力学模拟和分子对接研究，以揭示其高活性和选择性的机理。最后，提出了5-HT1AR的逐步9_24诱导信号转导机制。
• [EN] LIPOXYGENASE INHIBITORS<br/>[FR] INHIBITEURS DE LIPOXYGÉNASE
  申请人：STANFORD RES INST INT

  公开号：WO2021195346A1

  公开（公告）日：2021-09-30

  Various embodiments of the present disclosure are directed to compounds having Formula (I), Formula (IA), Formula (IB), Formula (IC), Formula (ID), Formula (IE), and/or pharmaceutically acceptable salts thereof. The compounds can be suitable for inhibiting lipoxygenases, and/or treating associated diseases, such as Alzheimer's disease. In some embodiments, the compounds may be administered to a patient as part of a pharmaceutical formulation.

  本公开的各种实施例涉及具有化学式(I)、化学式(IA)、化学式(IB)、化学式(IC)、化学式(ID)、化学式(IE)和/或其药学上可接受的盐的化合物。这些化合物可适用于抑制脂氧化酶，并/或治疗相关疾病，如阿尔茨海默病。在某些实施例中，这些化合物可作为药物配方的一部分向患者施用。

表征谱图