N-(3-phenylpropyl)-1,3-propanediamine | 67884-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-phenylpropyl)-1,3-propanediamine
• 英文别名: N-(3-phenyl-propyl)-propanediyldiamine；N-(3-Phenyl-propyl)-propandiyldiamin；3-(3-Phenyl-propylamino)-propylamin；3-(3-Phenylpropylamino)-propylamin；(3-Aminopropyl)(3-phenylpropyl)amine；N'-(3-phenylpropyl)propane-1,3-diamine
• CAS: 67884-81-5
• 化学式: C₁₂H₂₀N₂
• mdl: MFCD12803558
• 分子量: 192.304
• InChiKey: KVQFEIUOCUWSAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-phenylpropyl)-1,3-propanediamine 以 乙腈 为溶剂， 反应 42.0h， 生成 12-[(E)-hydroxyimino]-3,4,5,6,7,12-hexahydro-2H-4a-aza-1-azoniadibenzo[a,d]cyclooctene trifluoromethanesulfonate
  参考文献：
  名称：

  由2-硝基亚甲基-1-（ω-苯基烷基）咪唑烷或2-硝基亚甲基-1-（ω-苯基烷基）六氢嘧啶在三氟甲磺酸中环化合成6至10元环（E）-羟基亚氨基氢氮杂氮杂苯并环烯烃衍生物

  摘要：

  在三氟甲磺酸中，对2-硝基亚甲基-1-（ω-苯基烷基）咪唑烷或2-硝基亚甲基-1-（ω-苯基烷基）六氢嘧啶衍生物进行分子内环化，得到三氟甲磺酸盐形式的（E）-羟基亚氨基氢氮杂氮杂苯并环烯烃。该反应可能是通过形成亲电的瞬态羟基腈离子（或O质子化的丁腈氧化物）而发生的。除了较高元的环衍生物以外，产率通常是好的。

  DOI：

  10.1016/j.tet.2006.01.057
• 作为产物：
  描述：

  3-((3-phenylpropyl)amino)propanenitrile 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 反应 18.0h， 生成 N-(3-phenylpropyl)-1,3-propanediamine
  参考文献：
  名称：

  Antimalarial polyamine analogs

  摘要：

  A series of novel tetraamines of the general formula RNH(CH2)(x)NH(CH2)(y)(NH(CH2)(x)NHR was synthesized and examined for activity against growth of Plasmodium falciparum in vitro. Within the series, dibenzyl analogues (R = benzyl) were found to be the most effective growth inhibitors, with IC50 values of about 10-6 M. Further modifications of the tetraamine provided the optimum chain length for antimalarial activity of y = 7, x = 3. Compound 8 (MDL 27,695) with the structure y = 7, x = 3, R = benzyl, in combination with the ornithine decarboxylase inhibitor alpha-(difluoromethyl)ornithine, resulted in radical cures when tested against experimental Plasmodium berghei infections in mice. The structure-activity relationships of the series are discussed.

  DOI：

  10.1021/jm00106a015

文献信息

• Design and synthesis of a library of tertiary amides: Evaluation as mimetics of the melanocortins’ active core
  作者：Felikss Mutulis、Jana Kreicberga、Sviatlana Yahorava、Ilze Mutule、Larisa Borisova-Jan、Aleh Yahorau、Ruta Muceniece、Sandra Azena、Santa Veiksina、Ramona Petrovska

  DOI：10.1016/j.bmc.2007.06.003

  日期：2007.9.1

  acceptable results. According to this approach an efficient formation of Schiff bases was achieved in the presence of TiCl(4). Substances were isolated by reversed phase chromatography; in some cases isomers were additionally separated by chiral chromatography on Chirobiotic T. When tested on human recombinant melanocortin receptors all the tertiary amides showed some binding affinities; for the highest affinity

  在固相上制备了201种叔酰胺。将二胺偶联到活化的羧化王聚合物上，并使所得的聚合物取代的苄氧羰基保护的二胺与原甲酸三甲酯中的醛或酮反应，得到树脂连接的席夫碱。然后将偶联的树脂通过在4％的乙酸/原甲酸三甲酯中的氰基硼氢化钠还原为仲胺，然后在PyBroP和二异丙基乙胺的存在下用羧酸酰化。在清除剂（主要是1，2-乙二硫醇）存在下，通过三氟乙酸从树脂上裂解叔酰胺。当制备吲哚衍生物时，与连接体片段发生平行烷基化，得到2-（4-羟基苄基）-吲哚的衍生物作为副产物。在上述方法未给出可接受的结果的情况下，标题化合物的溶液合成或液相/固相混合制备被证明是有利的。根据这种方法，在TiCl（4）存在的情况下实现了席夫碱的有效形成。物质经反相色谱分离。在某些情况下，还可以通过在Chirobiotic T上进行手性色谱分离来分离异构体。在人重组黑皮质素受体上进行测试时，所有叔酰胺都表现出一定的结合亲和力。对于具有最高
• Cesium Effect:  High Chemoselectivity in Direct N-Alkylation of Amines
  作者：Ralph Nicholas Salvatore、Advait S. Nagle、Kyung Woon Jung

  DOI：10.1021/jo010643c

  日期：2002.2.1

  A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this

  为了有效地制备仲胺，使用铯碱开发了一种用于伯胺，二胺和多胺的单N-烷基化的新方法。铯碱不仅促进伯胺的烷基化，而且抑制产生的仲胺的过度烷基化。检查了各种胺，烷基溴化物和烷基磺酸盐，结果表明该方法具有较高的化学选择性，比单烷基化更有利于单-N-烷基化。特别地，使用空间要求高的底物或氨基酸衍生物可专门提供仲胺，在拟肽合成中具有广泛的应用。
• A Nanocrystal Catalyst Incorporating a Surface Bound Transition Metal to Induce Photocatalytic Sequential Electron Transfer Events
  作者：Jovan San Martin、Xianghua Zeng、Xihan Chen、Collin Miller、Chuang Han、Yixiong Lin、Nobuyuki Yamamoto、Xiaoming Wang、Sadegh Yazdi、Yanfa Yan、Matthew C. Beard、Yong Yan

  DOI：10.1021/jacs.1c00503

  日期：2021.8.4
• Expedient Protocol for Solid-Phase Synthesis of Secondary and Tertiary Amines
  作者：Christian A. Olsen、Matthias Witt、Jerzy W. Jaroszewski、Henrik Franzyk

  DOI：10.1021/ol049575h

  日期：2004.6.1

  An expedient solid-phase synthetic approach to secondary and tertiary amines was developed. The protocol employs conversion of resin-bound amino alcohols to the corresponding iodides, followed by iodide displacement with primary or secondary amines or with unprotected amino alcohols, This two-step procedure, affording products in good to excellent yields, is suitable for solid-phase synthesis of polyamines.
• CsOH-promoted chemoselective mono-N-alkylation of diamines and polyamines
  作者：Ralph N Salvatore、Shaun E Schmidt、Seung Il Shin、Advait S Nagle、Jay H Worrell、Kyung Woon Jung

  DOI：10.1016/s0040-4039(00)01747-0

  日期：2000.12

  Selective N-alkylation of diamines and polyamines was carried out using cesium hydroxide, 4 Angstrom molecular sieves, and DMF. This protocol was highly chemoselective, favoring mono-N-alkylation over overalkylations. (C) 2000 Published by Elsevier Science Ltd.