N-(2-Methoxy-1-methylethyl)aniline | 78923-90-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-Methoxy-1-methylethyl)aniline
• 英文别名: N-(2-methoxymethylethyl)aniline；N-(1-methoxypropan-2-yl)aniline
• CAS: 78923-90-7
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: HMGCMVSYMJILQV-UHFFFAOYSA-N

物化性质

• 沸点：
  68-70 °C(Press: 0.01 Torr)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-Methoxy-1-methylethyl)aniline 在 盐酸 、 三乙胺 作用下， 以 氯仿 、 水 为溶剂， 反应 9.0h， 生成 N-(羟基-2-丙基)苯胺
  参考文献：
  名称：

  在醚键的酸水解中异常的嵌合助剂的机理研究。第4部分

  摘要：

  N-（甲氧基丙-2-基）苯甲腈（1）的酸水解动力学研究是在75.1°C的8.84 M HCl和/或DCl中进行的。对2-（N-苯基氨基）丙醇（4）的形成进行了解释，并阐明了由酰胺基团辅助通过胺基异构体进行的初始醚裂解的机理。整个过程通过涉及两个中间体的三个步骤发展。各个过程的速率常数已通过UV和1 H NMR光谱技术确定。

  DOI：

  10.1016/s0040-4020(01)00285-x
• 作为产物：
  描述：

  1-甲氧基-2-丙酮 、 苯胺 在 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 反应 4.0h， 生成 N-(2-Methoxy-1-methylethyl)aniline
  参考文献：
  名称：

  新型吲哚烷基哌嗪衍生物作为选择性5-HT1A受体激动剂的设计，合成和结构-活性关系研究。

  摘要：

  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。

  DOI：

  10.1021/acs.jcim.9b00926

文献信息

• Mercury(II) Oxide/Tetrafluoroboric Acid; A Convenient Reagent for the Hydroxy(alkoxy)-phenylamination of Alkenes
  作者：José Barluenga、Luisa Alonso-Cires、Gregorio Asensio

  DOI：10.1055/s-1981-29456

  日期：——
• Comparative metabolism and elimination of acetanilide compounds by rat
  作者：K. L. Davison、G. L. Larsen、V. J. Feil

  DOI：10.3109/00498259409043297

  日期：1994.1

  1. C-14-labelled propachlor, alachlor, butachlor, metolachlor, methoxypropachlor and some of their mercapturic acid pathway metabolites (MAP) were given to rat either by gavage or by perfusion into a renal artery. MAP metabolites were isolated from bile and urine.2. Rat gavaged with propachlor and methoxypropachlor eliminated C-14 mostly in urine, whereas rat gavaged with alachlor, butachlor and metolachlor eliminated C-14 about equally divided between urine and faeces. When bile ducts were cannulated, the gavaged rat eliminated most of the C-14 in bile for all compounds. The amount of C-14 in bile from the propachlor-gavaged rat was less than that for the other acetanilides, with the difference being in the urine.3. The mercapturic acid metabolites 2-methylsulphinyl-N-(1-methylhydroxyethyl)-N-phenylacetamide and 2-methylsulphinyl-N-(1-methylmethoxyethyl)-N-phenylacetamide were isolated from the urine and bile of the methoxypropachlor-gavaged rat.4. Bile was the major route for C-14 elimination when MAP metabolites of alachlor, butachlor and metolachlor were perfused into a renal artery. Urine was the major route for C-14 elimination when MAP metabolites of propachlor and methoxypropachlor were perfused. Mercapturic acid conjugates were major metabolites in bile and urine when MAP metabolites were perfused.5. We conclude that alkyl groups on the phenyl portion of the acetanilide causes biliary elimination to be favoured over urinary elimination.
• 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。
• Mechanistic investigation of an anomalous anchimeric assistance in the acid hydrolysis of the ether linkage. Part 4
  作者：Antonio Arcelli、Romina Cecchi、Gianni Porzi、Samuele Rinaldi、Sergio Sandri

  DOI：10.1016/s0040-4020(01)00285-x

  日期：2001.4

  Kinetic investigation of the acid hydrolysis of N-(methoxyprop-2-yl)benzanilide (1) was performed in 8.84 M HCl and/or DCl at 75.1°C. The formation of 2-(N-phenylamino)propanol (4) was explained and the mechanism, involving an initial ether cleavage anchimerically assisted by the amide group, was clarified. The overall process evolves through three steps involving two intermediates. The rate constants

  N-（甲氧基丙-2-基）苯甲腈（1）的酸水解动力学研究是在75.1°C的8.84 M HCl和/或DCl中进行的。对2-（N-苯基氨基）丙醇（4）的形成进行了解释，并阐明了由酰胺基团辅助通过胺基异构体进行的初始醚裂解的机理。整个过程通过涉及两个中间体的三个步骤发展。各个过程的速率常数已通过UV和1 H NMR光谱技术确定。