2-ethenyl-N-2-propenyl-benzenemethanamine | 774181-39-4

• 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: 2-ethenyl-N-2-propenyl-benzenemethanamine
• 英文别名: N-(2-ethenylphenylmethyl)prop-2-enylamine；N-allyl-(2-vinylbenzyl)amine；N-[(2-ethenylphenyl)methyl]prop-2-en-1-amine
• CAS: 774181-39-4
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: VRIFFQMLYFOPQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2-ethenyl-N-2-propenyl-benzenemethanamine 在 [RuHCl(CO)(PPh₃)₃] 、 Hoveyda-Grubbs catalyst second generation 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 2.58h， 生成 8-phenylbenzo[5,6]isoindolo[1,2-a]isoquinoline-9,14-dione
  参考文献：
  名称：

  一锅烯烃异构化/脂胺式环封闭复分解/氧化/ 1,3-偶极环加成法合成异吲哚并[1,2-a]异喹啉

  摘要：

  N-烷基-N-（2-乙烯基苄基）prop-2-en-1-胺衍生物经历一锅烯烃异构化/脂族烯胺闭环复分解（RCM）/氧化/ 1,3-偶极环加成序列，钌络合物Ru（CO）HCl（PPh 3）3，第二代Hoveyda-Grubbs催化剂和1,3-双极性亲和剂。总体而言，在一次操作中，反应序列通过三个独特的钌催化转化，将简单的苄胺衍生物转化为具有π共轭四环系统的异吲哚并[1,2- a ]异喹啉。

  DOI：

  10.1002/adsc.201500680
• 作为产物：
  描述：

  2-乙烯基苯甲醛 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-ethenyl-N-2-propenyl-benzenemethanamine
  参考文献：
  名称：

  一锅烯烃异构化/脂胺式环封闭复分解/氧化/ 1,3-偶极环加成法合成异吲哚并[1,2-a]异喹啉

  摘要：

  N-烷基-N-（2-乙烯基苄基）prop-2-en-1-胺衍生物经历一锅烯烃异构化/脂族烯胺闭环复分解（RCM）/氧化/ 1,3-偶极环加成序列，钌络合物Ru（CO）HCl（PPh 3）3，第二代Hoveyda-Grubbs催化剂和1,3-双极性亲和剂。总体而言，在一次操作中，反应序列通过三个独特的钌催化转化，将简单的苄胺衍生物转化为具有π共轭四环系统的异吲哚并[1,2- a ]异喹啉。

  DOI：

  10.1002/adsc.201500680

文献信息

• Synthesis of 5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-ones: selective antagonists of muscarinic (M3) receptors
  作者：Benjamin Bradshaw、Paul Evans、Jane Fletcher、Alan T. L. Lee、Paul G. Mwashimba、Daniel Oehlrich、Eric J. Thomas、Robin H. Davies、Benjamin C. P. Allen、Kenneth J. Broadley、Amar Hamrouni、Christine Escargueil

  DOI：10.1039/b801206g

  日期：——

  Two approaches to tetrahydro-[1H]-2-benzazepin-4-ones of interest as potentially selective, muscarinic (M3) receptor antagonists have been developed. Base promoted addition of 2-(tert-butoxycarbonylamino)methyl-1,3-dithiane 5 with 2-(tert-butyldimethylsiloxymethyl)benzyl chloride 14 gave the corresponding 2,2-dialkylated 1,3-dithiane 15 which was taken through to the dithiane derivative 19 of the parent 2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-one by desilylation, oxidation and cyclisation via a reductive amination. After conversion into the N-tert-butyloxycarbonyl, N-toluene p-sulfonyl and N-benzyl derivatives 20–22, hydrolysis of the dithiane gave the N-protected tetrahydro-[1H]-2-benzazepin-4-ones 23–25. However, preliminary attempts to convert these into 5-cycloalkyl-5-hydroxy derivatives were not successful. In the second approach, ring-closing metathesis was used to prepare 2,3-dihydro-[1H]-2-benzazepines which were hydroxylated and oxidized to give the required 5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-ones. Following preliminary studies, ring-closing metathesis of the dienyl N-(2-nitrophenyl)sulfonamide 48 gave the dihydrobenzazepine 50 which was converted into the 2-butyl-5-cyclobutyl-5-hydroxytetrahydrobenzazepin-4-one 55 by hydroxylation and N-deprotection followed by N-alkylation via reductive amination, and oxidation. This chemistry was then used to prepare the 2-[(N-arylmethyl)aminoalkyl analogues 69, 72, 76 and 78. N-Acylation followed by amide reduction using the borane–tetrahydrofuran complex was also used to achieve N-alkylation of dihydrobenzazepines and this approach was used to prepare the 5-cyclopentyl-5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-one 103 and the 5-cyclobutyl-8-fluoro-5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-one 126. The structures of 2-tert-butyloxycarbonyl-4,4-propylenedithio-2,3,4,5-tetrahydro-[1H]-2-benzazepine 20 and (4RS,5SR)-2-butyl-5-cyclobutyl-4,5-dihydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepine 53 were confirmed by X-ray diffraction. The racemic 5-cycloalkyl-5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-ones were screened for muscarinic receptor antagonism. For M3 receptors from guinea pig ileum, these compounds had log10KB values of up to 7.2 with selectivities over M2 receptors from guinea pig left atria of approximately 40.

  针对四氢-[1H]-2-苯并氮杂环-4-酮作为潜在选择性毒蕈碱（M3）受体拮抗剂，已开发出两种合成途径。通过碱促反应，将2-(叔丁氧羰基氨基)甲基-1,3-二硫杂环烷-5与2-(叔丁基二甲基硅氧基甲基)苯甲基氯化物-14反应，得到了相应的2,2-二烷基化的1,3-二硫杂环烷-15，然后通过去硅化、氧化和还原胺化反应合成了母体2,3,4,5-四氢-[1H]-2-苯并氮杂环-4-酮的二硫杂环烷衍生物-19。在转化为N-叔丁氧羰基、N-甲苯p-磺酰基和N-苄基衍生物-20至-22后，二硫杂环烷的水解得到了N保护的四氢-[1H]-2-苯并氮杂环-4-酮-23至-25。然而，初步尝试将这些化合物转化为5-环烷基-5-羟基衍生物未成功。在第二种方法中，采用环闭合钠发生反应制备了2,3-二氢-[1H]-2-苯并氮杂环，并对其进行羟基化和氧化，得到所需的5-羟基-2,3,4,5-四氢-[1H]-2-苯并氮杂环-4-酮。经过初步研究，dienyl N-(2-硝基苯基)磺酰胺-48的环闭合钠发生反应生成了二氢苯并氮杂环-50，随后通过羟基化和去保护N基，再通过还原胺化进行N-烷基化和氧化，得到了2-丁基-5-环丁基-5-羟基四氢苯并氮杂环-4-酮-55。该化学反应进一步用于合成2-[(N-芳基甲基)氨基烷基]类似物-69、72、76和78。采用N-酰化，然后使用硼烷–四氢呋喃络合物进行酰胺还原，也用于实现二氢苯并氮杂环的N-烷基化，此方法可合成5-环戟基-5-羟基-2,3,4,5-四氢-[1H]-2-苯并氮杂环-4-酮-103和5-环丁基-8-氟-5-羟基-2,3,4,5-四氢-[1H]-2-苯并氮杂环-4-酮-126。2-叔丁氧羰基-4,4-丙烯二硫-2,3,4,5-四氢-[1H]-2-苯并氮杂环-20和(4RS,5SR)-2-丁基-5-环丁基-4,5-二羟基-2,3,4,5-四氢-[1H]-2-苯并氮杂环-53的结构通过X射线衍射得到确认。对外消旋的5-环烷基-5-羟基-2,3,4,5-四氢-[1H]-2-苯并氮杂环-4-酮进行了毒蕈碱受体拮抗活性筛选。在来自豚鼠回肠的M3受体实验中，这些化合物的log10KB值最高可达7.2，对来自豚鼠左心房的M2受体的选择性约为40。
• [EN] CYCLOPROPENIUM POLYMERS AND METHODS FOR MAKING THE SAME<br/>[FR] POLYMÈRES DE CYCLOPROPÉNIUM ET LEURS PROCÉDÉS DE FABRICATION
  申请人：UNIV COLUMBIA

  公开号：WO2014022365A1

  公开（公告）日：2014-02-06

  The present invention provides, inter alia, a process for incorporating a cyclopropenium ion into a polymeric system. Processes for making cross-linked polymers, linear polymers, and dendritic polymers, as well as for incorporating a cyclopropenium ion onto a preformed polymer are also provided. Further provided are stable, polycationic compounds, various polymers that contain stable cyclopropenium cations, and substrates containing such polymers. The use of these polymers in water purification systems, antimicrobial coatings, ion-transport membranes, cell supports, drug delivery vehicles, and gene therapeutic vectors are also provided.

  本发明提供了将环丙烯离子引入聚合体系的方法。还提供了制备交联聚合物、线性聚合物和树枝状聚合物的方法，以及将环丙烯离子引入预先形成的聚合物的方法。此外，还提供了稳定的多阳离子化合物、含有稳定环丙烯阳离子的各种聚合物，以及含有这些聚合物的基板。还提供了在水净化系统、抗微生物涂层、离子传输膜、细胞支撑、药物输送载体和基因治疗载体中使用这些聚合物的方法。
• Determining the scope of the lanthanide mediated, sequential hydroamination/C–C cyclization reaction: formation of tricyclic and tetracyclic aromatic nitrogen heterocycles
  作者：Gary A. Molander、Shawn K. Pack

  DOI：10.1016/j.tet.2003.08.071

  日期：2003.12

  also varied to determine how it affected the cascade reaction. It was found that the benzo[a]quinolizine and the pyrido[2,1,a]isoindolizine ring systems formed with the highest diastereoselectivity (>20:1), regardless of the electronic characteristics of the aromatic ring. Additionally, a tetracyclic indole nitrogen heterocycle was formed with a 2.3:1 diastereomeric ratio. A novel procedure for substrate

  确定了镧系元素介导的顺序加氢胺化/ CC环化反应的范围，以形成三环和四环芳族氮杂环。探索了一系列的环大小以确定非对映选择性。还改变了芳环的电子特性，以确定其如何影响级联反应。结果发现，在苯并[一个]喹嗪和吡啶并[2,1，一个（> 20：1）具有最高的非对映选择性形成异吲环系统，而不管芳香环的电子特性。另外，形成具有2.3：1非对映异构体比率的四环吲哚氮杂环。还提出了用于底物制备的新方法。
• CYCLOPROPENIUM POLYMERS AND METHODS FOR MAKING THE SAME
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20150175727A1

  公开（公告）日：2015-06-25

  The present invention provides, inter alia, a process for incorporating a cyclopropenium ion into a polymeric system. Processes for making cross-linked polymers, linear polymers, and dendritic polymers, as well as for incorporating a cyclopropenium ion onto a preformed polymer are also provided. Further provided are stable, polycationic compounds, various polymers that contain stable cyclopropenium cations, and substrates containing such polymers. The use of these polymers in water purification systems, antimicrobial coatings, ion-transport membranes, cell supports, drug delivery vehicles, and gene therapeutic vectors are also provided.

  本发明提供了将环丙烯阳离子引入到聚合体系中的方法。还提供了制备交联聚合物、线性聚合物和树枝状聚合物的方法，以及将环丙烯阳离子引入到预制聚合物上的方法。此外，还提供了稳定的多阳离子化合物，包含稳定的环丙烯阳离子的各种聚合物，以及含有这些聚合物的基底。此外，还提供了在水处理系统、抗微生物涂层、离子传输膜、细胞支持、药物传递载体和基因治疗载体中使用这些聚合物的方法。
• DICYCLOPENTADIENE METATHESIS POLYMERISATION CATALYST
  申请人：Limited Liability Company "United Research and Development Centre"

  公开号：EP2280033A1

  公开（公告）日：2011-02-02

  This invention relates catalysis and concerns production of catalyst for dicyclopentadiene (DCPD) ring-opening metathesis polymerization. Catalyst for metathesis polymerization has the formula: where L is a substituent selected from the group: Several methods of the catalyst preparation were developed: Method of preparing catalyst having the following formula where L where the second generation Grubbs catalyst is subject to interaction with (N,N-dialkyl-(2-vinylbenzyl)amine or 1-(2- vinylbenzyl)pyrrolidine or 4-(2- vinylbenzyl)morpholine in inert atmosphere at temperatures of 60-85 °C in the presence of a solvent, with dialkyl- being methylethyl- or methyl(2-metoxyethyl). Method of preparing catalyst having the following formula where L is a substituent selected from the group: where triphenylphosphine complex of ruthenium is subject to interaction with 1,1-diphenyl-2-propyne-1-ol in tetrahydrofuran at the temperature of solvent boiling in inert atmosphere, and then with tricyclohexylphosphine at room temperature in inert atmosphere; indenylidene complex of ruthenium formed is recovered and then step by step, in one reactor, it is subject to interaction with 1,3-Bis(2,4,6-trimethylphenyl)-2-(trichloromethyl)imidazolidine and 2-(N,N-dialkylaminomethyl)styrene or 1-(2-vinylbenzyl) pyrrolidine HJIH 4-(2- vinylbenzyl)morpholine in toluene with heating at 60-70°C in inert atmosphere, with dialkyl- being dimethyl, diethyl-, or methylethyl- or methyl(2-metoxyethyl)-. Method of metathesis polymerization of dicyclopentadiene has been also developed where polymerization is carried out with the catalyst of item 1 with mole ratio of substrate to catalyst of 70000:1 to 200000:1. Invention allows increasing of the catalyst yield and simplifies schemes of synthesis through reducing number of stages, as well as preparing polydicyclopentadiene with high application properties.

  本发明与催化有关，涉及双环戊二烯（DCPD）开环偏聚催化剂的生产。 元合成聚合催化剂的化学式为 其中 L 是选自以下组别的取代基： 已开发出几种催化剂制备方法： 制备下式催化剂的方法 其中 L 第二代 Grubbs 催化剂与 N,N-二烷基-(2-乙烯基苄基)胺或 1-(2-乙烯基苄基)吡咯烷或 4-(2-乙烯基苄基)吗啉在惰性气氛中于 60-85 ℃温度下在溶剂存在下发生作用，其中二烷基为甲基乙基或甲基(2-甲氧基乙基)。 制备下式催化剂的方法 其中 L 是选自以下组别的取代基： 其中钌的三苯基膦络合物在溶剂沸腾温度和惰性气氛下与四氢呋喃中的 1,1-二苯基-2-丙炔-1-醇作用，然后在室温和惰性气氛下与三环己基膦作用；回收形成的钌的亚茚基络合物，然后在一个反应器中逐步与 1,3-双（2,4,6-三甲基苯基）-2-（三氯甲基）咪唑烷和 2-（N、N-二烷基氨基甲基)苯乙烯或 1-(2-乙烯基苄基)吡咯烷 HJIH 4-(2-乙烯基苄基)吗啉在甲苯中发生作用，在 60-70°C 的惰性气氛中加热，二烷基为二甲基、二乙基或甲基乙基或甲基(2-甲氧基乙基)。 此外，还开发了二环戊二烯的偏合成聚合方法，使用第 1 项催化剂进行聚合时，底物与催化剂的摩尔比为 70000:1 至 200000:1。 本发明通过减少阶段数量，提高了催化剂产量，简化了合成方案，并制备出具有高应用特性的聚二环戊二烯。