(Z)-4-(4-chlorophenyl)but-3-enylamine | 198782-82-0

• 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: (Z)-4-(4-chlorophenyl)but-3-enylamine
• 英文别名: (Z)-4-(4-chlorophenyl)but-3-en-1-amine；(Z)-4-(p-chlorophenyl)-3-butenylamine；(Z)-4-(4-chlorophenyl)-3-butenylamine
• CAS: 198782-82-0
• 化学式: C₁₀H₁₂ClN
• 分子量: 181.665
• InChiKey: PWRHSRMALBVIQZ-IWQZZHSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-4-(4-chlorophenyl)but-3-enylamine 在 四氯化锡 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 diethyl 1,6-cis-6,7-trans-3-benzyl-7-(4-chlorophenyl)-2-oxo-3-azabicyclo[4.2.0]octane-8,8-dicarboxylate
  参考文献：
  名称：

  乙烯羧酸与苯乙烯和卤代苯乙烯的分子间和分子内环加成反应

  摘要：

  已经研究了三羧酸乙烯酯与苯乙烯和α-卤代苯乙烯的分子间和分子内环加成反应。在SnCl 4或SnBr 4的存在下，三羧酸乙烯酯与苯乙烯或α-溴苯乙烯的反应有选择地产生2，4-顺式取代的环丁烷。一系列苯乙烯官能化的乙烯三羧酸酰胺（包括原位生成的衍生物）的分子内环加成反应根据底物的结构和取代基显示出高的反应模式多样性。基于DFT计算，讨论了反应的区域选择性和立体选择性以及反应机理。

  DOI：

  10.1055/s-0040-1706547
• 作为产物：
  描述：

  (Z)-N-(4-(4-chlorophenyl)but-3-enyl)phthalimide 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以63%的产率得到(Z)-4-(4-chlorophenyl)but-3-enylamine
  参考文献：
  名称：

  Brønsted Acid-Catalyzed Intramolecular Hydroamination of Protected Alkenylamines. Synthesis of Pyrrolidines and Piperidines

  摘要：

  [GRAPHIC]The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-Phenylanilides also underwent cyclization to form gamma-lactams.

  DOI：

  10.1021/ol025659j

文献信息

• Naftifine-analogues as anti-Trypanosoma cruzi agents
  作者：Alejandra Gerpe、Lucía Boiani、Paola Hernández、Maximiliano Sortino、Susana Zacchino、Mercedes González、Hugo Cerecetto

  DOI：10.1016/j.ejmech.2010.01.052

  日期：2010.6

  oxidative stress. Here, we describe the synthesis and the activity of new containing bioactive-heterocycles analogues of naftifine as potential T. cruzi membrane sterol biosynthesis inhibitors. Benzimidazole 1,3-dioxides (11 and 13) and quinoxaline 1,4-dioxides (22 and 23) displayed excellent parasite/mammal selectivity indexes. Analysis of the free sterols from parasite incubated with the compounds

  恰加斯病是中美洲和南美洲的一个相关健康问题。一线治疗是尼呋替莫克斯和苯并咪唑，它们有很多缺点，需要快速产生治疗选择。基于我们对氮杂硫杂杂环化合物作为抗克氏锥虫的研究，我们确定了可通过氧化应激起作用的药效基团。在这里，我们描述了萘菲芬新的生物活性杂环类似物作为潜在的克鲁斯膜固醇生物合成抑制剂的合成和活性。苯并咪唑1,3-二氧化物（11和13）和喹喔啉1,4-二氧化物（22和23））显示出极好的寄生虫/哺乳动物选择性指数。分析与化合物孵育的寄生虫产生的游离固醇，表明它们中的任何一个都能积聚角鲨烯，这表明在抗T. cruzi的作用机理中不涉及对固醇生物合成的抑制。还测试了一些衍生物作为抗真菌剂。在本工作中获得的结果为这些传染病打开了新化合物的潜在治疗可能性。
• Anhydrolide Macrolides. 1. Synthesis and Antibacterial Activity of 2,3-Anhydro-6-<i>O</i>-methyl 11,12-Carbamate Erythromycin A Analogues
  作者：Richard L. Elliott、Daisy Pireh、George Griesgraber、Angela M. Nilius、Patty J. Ewing、Mai Ha Bui、Patti M. Raney、Robert K. Flamm、Ki Kim、Rodger F. Henry、Daniel T. W. Chu、Jacob J. Plattner、Yat Sun Or

  DOI：10.1021/jm970547x

  日期：1998.5.1

  A series of 3-descladinosyl-2,3-anhydro-6-O-methylerythromycin A 11,12-carbamate analogues have been synthesized and evaluated for antibacterial activity. These compounds were found to be potent antibacterial agents against Gram-positive organisms in vitro, many having MIC values below 1 mu g/mL for the macrolide-susceptible Staphylococcus aureus, Streptococcus pyogenes, and Streptococcus pneumoniae, as well as improved activity compared to erythromycin A against the inducibly MLS (macrolide, lincosamide, and streptogramin B)-resistant organisms. Structure-activity studies revealed that arylalkyl carbamates with two and four carbon atoms between the aromatic moiety and carbamate nitrogen have the best in vitro activity. All of the C-10 epi analogues evaluated were found to have substantially less activity than the corresponding natural C-10 isomer. Several analogues demonstrated moderate antibacterial activity against the constitutively resistant S. aureus A-5278, S. pneumoniae 5979, and S. pyogenes 930. However, despite potent in vitro activity, these analogues showed only moderate in vivo activity in mouse protection studies.
• Convenient Route to Primary (<i>Z</i>)-Allyl Amines and Homologs
  作者：Alejandra Gerpe、Mariela Bollini、Mercedes González、Hugo Cerecetto

  DOI：10.1080/00397910802369596

  日期：2008.12.16

  A convenient two-step procedure for the synthesis of primary (Z)-allyl amines, (Z)-homoallyl amines [(Z)-but-3-enylamines], and (Z)-pent-4-enylamines using the Wittig reaction was achieved. The use of nonstabilized ylides from triphenylphosphonium salt, potassium salt, and apolar solvent produced (Z/E)geometric isomer ratios generally greater than 1.6. The amine moiety was masked using a phtalimide group that was removed successfully in the last step of the process in two different conditions, NH2NH2/EtOH/rt or CH3NH2/EtOH/rt. However, in some cases, reduction of the C=C double bond in the deprotection with hydrazine was concomitantly observed.
• [EN] 2-(AMINOMETHYL)ARYLAMIDE ANALGESICS<br/>[FR] ANALGESIQUES A BASE DE 2-(AMINOMETHYL)ARYLAMIDE
  申请人：PHARMACOPEIA DRUG DISCOVERY

  公开号：WO2004071445A2

  公开（公告）日：2004-08-26

  A chemical genus of 2-(aminomethyl)arylamides, which are useful as analgesics, is disclosed. The genus is represented by the Formula I: a representative example is:
• Inter- and Intramolecular Cycloaddition Reactions of Ethenetricarboxylates with Styrenes and Halostyrenes
  作者：Shoko Yamazaki、Zhichao Wang、Kentaro Iwata、Khotaro Katayama、Hirotaka Sugiura、Yuji Mikata、Tsumoru Morimoto、Akiya Ogawa

  DOI：10.1055/s-0040-1706547

  日期：2021.2

  Inter- and intramolecular cycloaddition reactions of ethenetricarboxylates with styrenes and α-halostyrenes have been investigated. The reactions of ethenetricarboxylates with styrenes or α-bromostyrenes in the presence of SnCl4 or SnBr4 stereoselectively gave 2,4-cis-substituted cyclobutanes. The intramolecular cycloaddition reactions of a series of styrene-functionalized ethenetricarboxylate amides

  已经研究了三羧酸乙烯酯与苯乙烯和α-卤代苯乙烯的分子间和分子内环加成反应。在SnCl 4或SnBr 4的存在下，三羧酸乙烯酯与苯乙烯或α-溴苯乙烯的反应有选择地产生2，4-顺式取代的环丁烷。一系列苯乙烯官能化的乙烯三羧酸酰胺（包括原位生成的衍生物）的分子内环加成反应根据底物的结构和取代基显示出高的反应模式多样性。基于DFT计算，讨论了反应的区域选择性和立体选择性以及反应机理。