4-methyl-N-[(2E)-3-phenylprop-2-en-1-yl]aniline | 127598-83-8

• 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: 4-methyl-N-[(2E)-3-phenylprop-2-en-1-yl]aniline
• 英文别名: N-trans-cinnamyl-4-methylbenzeneamine；N-cinnamyl-4-methylaniline；N-cinnamyl-p-toluidine；4-methyl-N-[(E)-3-phenylprop-2-enyl]aniline
• CAS: 127598-83-8
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: XCQQNUAZHXOTJO-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  4-methyl-N-[(2E)-3-phenylprop-2-en-1-yl]aniline 在 polyphosphoric acid 作用下， 反应 6.0h， 生成 4-Phenyl-6-methyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  铜催化水合二羧酸二叔丁酯的氧催化氧化成偶氮二甲酸二叔丁酯及其在温和条件下对1,2,3,4-四氢喹啉的脱氢作用

  摘要：

  用均相的CuI和偶氮二甲酸二叔丁酯开发了一种新型的共催化体系，用于在温和条件下对1,2,3,4-四氢喹啉进行好氧脱氢。发达共催化体系是由二-叔丁基偶氮二羧酸酯介导的二- 1,2,3,4-四氢喹啉和好氧氧化再生的脱氢叔丁基偶氮二羧酸酯选自二叔使用分子氧作为丁基hydrazodicarboxylate终端氧化剂。发达的铜和偶氮二羧酸二叔丁酯助催化体系有效地合成了各种喹啉。

  DOI：

  10.1021/acs.orglett.6b03166
• 作为产物：
  描述：

  cinnamaldehyde anil 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以17.75 g的产率得到4-methyl-N-[(2E)-3-phenylprop-2-en-1-yl]aniline
  参考文献：
  名称：

  级联酰化/ IMDAV /烯反应序列的第一个例子，导致N-芳基苯并[ f ]异吲哚-4-羧酸具有抗病毒活性

  摘要：

  易于获得的N-芳基-3-苯基烯丙基胺与马来酸酐之间的反应产生了意想不到的产物-多取代的氢化苯并[ f ]异吲哚-4-羧酸。：这种转变通过的步骤的以前未知的序列前进Ñ与马来酸酐，在中间的乙烯基芳烃的分子内Diels-Alder反应的烯丙胺的酰化Ñ -maleamide，并且前两个步骤的产物的阿尔德烯反应。选定的苯并[ f ]异吲哚显示出抗病毒活性。

  DOI：

  10.1016/j.tetlet.2018.02.015

文献信息

• Co(II) PCP Pincer Complexes as Catalysts for the Alkylation of Aromatic Amines with Primary Alcohols
  作者：Matthias Mastalir、Gerald Tomsu、Ernst Pittenauer、Günter Allmaier、Karl Kirchner

  DOI：10.1021/acs.orglett.6b01647

  日期：2016.7.15

  Efficient alkylations of amines by alcohols catalyzed by well-defined Co(II) complexes are described that are stabilized by a PCP ligand (N,N′-bis(diisopropylphosphino)-N,N′-dimethyl-1,3-diaminobenzene) based on the 1,3-diaminobenzene scaffold. This reaction is an environmentally benign process implementing inexpensive, earth-abundant nonprecious metal catalysts and is based on the acceptorless alcohol

  描述了由定义明确的Co（II）配合物催化的醇对胺的有效烷基化作用，并通过PCP配体（基于N，N'-双（二异丙基膦基）-N，N'-二甲基-1,3-二氨基苯）稳定化在1,3-二氨基苯支架上 该反应是一种环境友好的方法，采用廉价的，富含地球的非贵金属催化剂，并且基于无受体醇脱氢概念。一系列伯醇和芳族胺以良好或优异的分离收率有效地转化为单-N-烷基化胺。
• Solvent-Free Synthesis, DNA-Topoisomerase II Activity and Molecular Docking Study of New Asymmetrically N,N'-Substituted Ureas
  作者：Andressa Esteves-Souza、Claudio Rodrigues-Santos、Catarina Del Cistia、Daniel Silva、Carlos Sant'Anna、Aurea Echevarria

  DOI：10.3390/molecules171112882

  日期：——

  A new series of asymmetrically N,N'-substituted ureas 20–25 was prepared using solvent free conditions, which is an eco-friendly methodology, starting with Schiff bases derived from cinnamaldehyde and p-substituted anilines, which are subsequently submitted to reduction reactions that afford the corresponding asymmetric secondary amines. All of the intermediates were prepared using solvent free reactions, which were compared to traditional methodologies. All of the reactions required a remarkably short amount of time and provided good yields when solvent free conditions were employed compared to other methodologies. The DNA-topoisomerase II-α (topo II-α) activity was evaluated in relaxation assays, which showed that all of the compounds inhibited the enzyme activity at 10 μM, except for urea 24. Furthermore, a molecular docking study indicated that the compounds 20–25 binding to the topo II-α are able to interact with the same binding site as the anticancer drug etoposide, suggesting that the ureas could inhibit the enzyme by the same mechanism of action observed for etoposide, which prevents re-ligation of the DNA strands.

  采用无溶剂条件，以肉桂醛和p位取代的苯胺衍生的希夫碱为原料，经还原反应制得相应的非对称次级胺，进而合成了新系列非对称N,N'-取代的脲类化合物20–25。该方法是一种绿色环保的方法。所有中间体的制备均采用无溶剂反应，并与传统方法进行了比较。所有反应所需时间都极短，且在采用无溶剂条件时的产率普遍高于其他方法。通过松弛实验评估了这些化合物对DNA拓扑异构酶II-α（topo II-α）的活性。结果表明，除脲24外，所有化合物在10 μM浓度下均抑制酶活性。此外，分子对接研究显示，化合物20–25与topo II-α的结合位点与抗癌药物依托泊苷相同，这表明脲类化合物可能通过类似依托泊苷的机制抑制酶活性，即阻止DNA链的再连接。
• Efficient Protocol for Reductive Amination of Aldehydes and Ketones with Sodium Borohydride in an Ionic Liquid/H₂O System
  作者：K. Nagaiah、V. Naveen Kumar、R. Srinivasa Rao、B. V. S. Reddy、A. V. Narsaiah、J. S. Yadav

  DOI：10.1080/00397910600941356

  日期：2006.11.1

  Abstract The imines were generated in situ from carbonyl compounds and amines, which undergo smooth reduction with sodium borohydride in an ionic liquid/H2O solvent system. The reaction conditions were very mild and neutral to afford the corresponding highly functionalized amines in excellent yields. IICT Communication No. 041013.

  摘要 亚胺是由羰基化合物和胺原位生成的，它们在离子液体/H2O 溶剂系统中与硼氢化钠进行平滑还原。反应条件非常温和和中性，以极好的收率提供相应的高度官能化胺。IICT 通讯第 041013 号。
• Air Stable Iron(II) PNP Pincer Complexes as Efficient Catalysts for the Selective Alkylation of Amines with Alcohols
  作者：Matthias Mastalir、Berthold Stöger、Ernst Pittenauer、Michael Puchberger、Günter Allmaier、Karl Kirchner

  DOI：10.1002/adsc.201600689

  日期：2016.12.7

  A series of well‐defined iron(II) complexes of the types [Fe(PNP)Br2] and [Fe(PNP)(CO)Br2] with PNP pincer ligands based on triazine and pyridine backbones were prepared and fully characterized. These complexes were tested as catalysts for the alkylation of amines by alcohols. The high‐spin complexes [Fe(PNP)Br2] are catalytically inactive. The low‐spin complexes [Fe(PNP)(CO)Br2] bearing a carbonyl

  制备了一系列具有明确定义的铁（II）配合物，其类型为[Fe（PNP）Br 2 ]和[Fe（PNP）（CO）Br 2 ]，具有基于三嗪和吡啶骨架的PNP钳形配体。测试了这些络合物作为胺被醇烷基化的催化剂。高自旋络合物[Fe（PNP）Br 2 ]具有催化活性。带有羰基共配体的低自旋络合物[Fe（PNP）（CO）Br 2 ]有效地和选择性地将伯醇以及芳族和苄基胺选择性地转化为单N烷基化胺，分离率高至优异。给出了机械的建议。
• Observations on the vilsmeier reaction Part 2. The anomalaus reaction of N-benzyl N-cyanoethyl-4-methylaniline derivatives
  作者：Andrew P. Shawcross、Stephen P. Stanforth

  DOI：10.1016/s0040-4020(01)89174-2

  日期：——

  The reaction of a series of the title anilines (1) with variously substituted benzyl groups under Vilsmeier conditions was investigated. Only perfluorobenzyl derivatives showed normal formylation while other fluoro derivatives gave mixed results and other substituents gave solely the anomalous amine (5) together with the aldehyde (6) derived from the benzyl group.

  研究了一系列标题苯胺（1）在Vilsmeier条件下与各种取代的苄基的反应。仅全氟苄基衍生物显示出正常的甲酰化，而其他氟衍生物给出了混合的结果，其他取代基仅给出了异常胺（5）和衍生自苄基的醛（6）。