(R/S)-N,N-dimethyl-(3-phenylbutyl)amine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R/S)-N,N-dimethyl-(3-phenylbutyl)amine
• 英文别名: 1-Dimethylamino-3-phenylbutan；N,N-Dimethyl-3-phenyl-butylamin；N,N-dimethyl-3-phenylbutanamine；(+/-)-dimethyl-(3-phenyl-butyl)-amine；Dimethyl-(γ-phenyl-butyl)-amin；4-Dimethylamino-2-phenyl-butan；N,N-dimethyl-3-phenylbutan-1-amine
• 化学式: C₁₂H₁₉N
• 分子量: 177.29
• InChiKey: GAICVPVDFBPSME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R/S)-N,N-dimethyl-(3-phenylbutyl)amine 在 双氧水 作用下， 125.0 ℃ 、133.32 Pa 条件下， 生成 丁-3-烯-2-基苯
  参考文献：
  名称：

  Rokstad,O.A. et al., Acta Chemica Scandinavica (1947), 1969, vol. 23, p. 782 - 790

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-N,N-dimethyl-3-phenylbut-2-en-1-amine 在 氢气 作用下， 以 乙醇 为溶剂， 反应 30.0h， 以95%的产率得到(R/S)-N,N-dimethyl-(3-phenylbutyl)amine
  参考文献：
  名称：

  Gaining in pan-affinity towards sigma 1 and sigma 2 receptors. SAR studies on arylalkylamines

  摘要：

  Sigma Receptor (SR) modulators are involved in different signal transduction pathways, representing important pharmacological/therapeutic tools in several pathological conditions, such as neurodegenerative diseases and cancers. To this purpose, numerous compounds have been developed in order to target selectively one of the two subtypes (S1R and S2R) as chemotherapeutic agent. However, experiments have also shown that ligands which are able to bind both SR subtypes can be useful for the diagnosis and/or the treatment of cancers. Therefore, the discovery of compounds with good affinity towards both S1R and S2R ('pan-modulators') is also of great interest and still represents a challenge up to now. For this reason, we synthesized novel arylalkylamines with the aim to obtain compounds with S1R and S2R affinity in the nM range and, by modeling quantitative structure-activity relationships (QSARs), we identified the essential structural features to obtain promising pan-compounds. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.10.005

文献信息

• MOF-derived cobalt nanoparticles catalyze a general synthesis of amines
  作者：Rajenahally V. Jagadeesh、Kathiravan Murugesan、Ahmad S. Alshammari、Helfried Neumann、Marga-Martina Pohl、Jörg Radnik、Matthias Beller

  DOI：10.1126/science.aan6245

  日期：2017.10.20

  preparation entailed template assembly of cobalt-diamine-dicarboxylic acid metal organic frameworks on carbon and subsequent pyrolysis under inert atmosphere. The resulting stable and reusable catalysts were active for synthesis of primary, secondary, tertiary, and N-methylamines (more than 140 examples). The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines

  MOF 为制造胺奠定了基础 还原胺化是化学家用来制造碳氮键的常用方法。该反应通常需要贵金属催化剂，将氨或其他胺与羰基化合物偶联，然后与氢气偶联。贾加迪什等人。报告了一类非贵重的钴纳米粒子，可在非常广泛的底物上催化这种反应，包括具有药用价值的复杂分子（参见 Chen 和 Xu 的观点）。钴首先嵌入金属有机框架 (MOF) 中，加热后转变为石墨壳。催化剂可以方便地从产品中分离出来，最多可循环使用六次。科学，这个问题 p。326; 另见第。304 由金属-有机骨架前体制备的钴纳米颗粒可催化非常广泛的还原胺化反应。用于合成药物相关化合物的贱金属催化剂的开发仍然是化学研究的一个重要目标。在这里，我们报告说，由石墨壳包裹的钴纳米颗粒是广泛有效的还原胺化催化剂。它们方便实用的制备需要在碳上模板组装钴-二胺-二羧酸金属有机骨架，然后在惰性气氛下热解。所得稳定且可重复使用的催化剂对于合成伯胺、仲胺、叔胺和 N-甲胺（超过
• Ultra-small cobalt nanoparticles from molecularly-defined Co–salen complexes for catalytic synthesis of amines
  作者：Thirusangumurugan Senthamarai、Vishwas G. Chandrashekhar、Manoj B. Gawande、Narayana V. Kalevaru、Radek Zbořil、Paul C. J. Kamer、Rajenahally V. Jagadeesh、Matthias Beller

  DOI：10.1039/c9sc04963k

  日期：——

  situ generated cobalt nanoparticles from molecularly defined complexes as efficient and selective catalysts for reductive amination reactions. In the presence of ammonia and hydrogen, cobalt–salen complexes such as cobalt(II)–N,N′-bis(salicylidene)-1,2-phenylenediamine produce ultra-small (2–4 nm) cobalt-nanoparticles embedded in a carbon–nitrogen framework. The resulting materials constitute stable,

  我们报告从分子定义的复合物为还原胺化反应的有效和选择性催化剂原位生成钴纳米粒子的合成。在存在氨和氢的情况下，钴-salen络合物，例如钴（II）-N，N'-双（水杨基亚烷基）-1,2-苯二胺产生嵌入碳-氮骨架中的超小（2-4 nm）钴纳米颗粒。所得的材料构成稳定的，可重复使用的和磁性可分离的催化剂，其使得能够由羰基化合物和氨合成直链和支链的苄基，杂环和脂族伯胺。分离的纳米颗粒还代表了用于合成伯胺，仲胺和叔胺（包括生物学上相关的N-甲基胺）的出色催化剂。
• Mechanistic Variations in Ionic Hydrogenation of Unsaturated Phosphine and Amine Boranes
  作者：Timothy S. De Vries、Supriyo Majumder、Angela M. Sandelin、Guoqiang Wang、Edwin Vedejs

  DOI：10.1021/ol2031203

  日期：2012.2.3

  Internal hydride transfer occurs when tethered carbocations are generated from unsaturated phosphine or phosphinite boranes. 3-Methylenecyclohexyl-derived boranes 12 or 18 react with MsOH to give ionic hydrogenation products with high syn-selectivity. With unsaturated amine boranes, initial hydrogen evolution gives BH2(OMs) complexes, but IH occurs using excess MsOH in a slower second stage. A diastereoselective

  当不饱和膦或次膦酸硼烷生成束缚碳正离子时，会发生内部氢化物转移。3-亚甲基环己基衍生的硼烷12或18与 MsOH 反应得到具有高顺选择性的离子氢化产物。对于不饱和胺硼烷，初始析氢产生 BH 2 (OMs) 配合物，但 IH 在较慢的第二阶段使用过量的 MsOH 发生。使用樟脑磺酸（第一阶段）和 MsOH（第二阶段）从26b发生非对映选择性反应，水解后得到 33（68% ee）。
• The Aminomethylation of Olefins. I. The Reaction of Secondary Amines, Formaldehyde, and Olefins
  作者：Claude J. Schmidle、Richard C. Mansfield

  DOI：10.1021/ja01622a058

  日期：1955.9
• v.Braun; Seemann; Schultheiss, Chemische Berichte, 1922, vol. 55, p. 3809
  作者：v.Braun、Seemann、Schultheiss

  DOI：——

  日期：——