N-benzylpent-4-en-2-amine | 88381-95-7

• 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-benzylpent-4-en-2-amine
• CAS: 88381-95-7
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: XNFSJJMFFMCCMG-UHFFFAOYSA-N

物化性质

• 沸点：
  248.8±19.0 °C(Predicted)
• 密度：
  0.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  N-benzylpent-4-en-2-amine 在 苯基氯化硒 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 以82%的产率得到1-Benzyl-4-chloro-2-methyl-pyrrolidine
  参考文献：
  名称：

  Synthesis of azetidines by electrophilic selenium-induced cyclization of homoallylic benzylamines

  摘要：

  Homoallyl benzylamines, prepared by allylation of the corresponding N-benzylimines, have been subjected to a selenium-induced cyclization under various conditions. At room temperature, the 4-exo and the 5-endo modes are competitive. In acetonitrile, the azetidine has been isolated as the major cyclization product, especially for homoallylamines derived from ketimines. With an excess of selenium reagent, 3-halopyrrolidines have been obtained. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00028-2
• 作为产物：
  描述：

  N-ethylidenebenzylamine N-oxide 在 magnesium 、 溶剂黄146 、 锌 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 N-benzylpent-4-en-2-amine
  参考文献：
  名称：

  Stereoselective Synthesis of Pyrrolidines and Pyrrolizidines by Intramolecular Carbolithiation

  摘要：

  本文介绍了制备取代的均烯丙基胺并将其转化为吡咯烷或吡咯烷的方法。各种均烯丙基仲胺与 (三丁基锡) 甲基磺酸盐发生 N-烷基化反应，随后进行锡锂交换，生成的有机锂发生分子内羰基化反应（阴离子环化反应）。在环化过程中，尤其是在生成 2,4-二取代的吡咯烷时，可获得较高的立体选择性。

  DOI：

  10.1055/s-2001-16074

文献信息

• A Cascade Aza-Cope/Aza-Prins Cyclization Leading to Piperidine Derivatives
  作者：Jothi L. Nallasivam、Rodney A. Fernandes

  DOI：10.1002/ejoc.201403607

  日期：2015.3

  The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines has been explored. The use of glyoxalic acid as the carbonyl component afforded bicyclic structures as a result of the internal carboxylate anion trapping the intermediate cation. The unimolecular bis-, tris-, and tetrakis(homoallylamine)s efficiently delivered the appended bis-, tris- and tetrakis(piperidine-4-ol)s

  已经探索了高烯丙基胺的级联 aza-Cope/aza-Prins 环化以产生取代的哌啶。由于内部羧酸根阴离子捕获中间阳离子，因此使用乙醛酸作为羰基组分提供双环结构。单分子双-、三-和四（高烯丙胺）有效地提供了附加的双-、三-和四（哌啶-4-醇）（分别为三脚架和十字架形状）作为新实体。后一种化合物在 Suzuki-Miyaura 交叉偶联反应中用作合成肠壳孔蛋白的极好配体。
• Hoffmann, Reinhard W.; Eichler, Guenter; Endesfelder, Andreas, Liebigs Annalen der Chemie, 1983, # 11, p. 2000 - 2007
  作者：Hoffmann, Reinhard W.、Eichler, Guenter、Endesfelder, Andreas

  DOI：——

  日期：——
• Synthesis of Azetidine and Pyrrolidine Derivatives through Selenium-Induced Cyclization of Secondary Homoallylamines − A77Se NMR Study
  作者：Xavier Pannecoucke、Francis Outurquin、Claude Paulmier

  DOI：10.1002/1099-0690(200203)2002:6<995::aid-ejoc995>3.0.co;2-a

  日期：2002.3

  Treatment of alpha-alkyl and alpha,alpha-dialkyl homoallylic amines I with PhSeX (X = Cl, Br, 1), in CH3CN containing sodium carbonate produced mixtures of azetidines 2 and pyrrolidines 3. The cyclization also occurred in the absence of Na2CO3, and the corresponding azetidinium and pyrrolidinium salts 2(HX) and 3(HX) were formed in CDCl3 or CH3CN. The crude reaction mixtures were analysed by Se-77 NMR. Each product - 2, 3, 2(HX), and 3(HX) - was characterized by its 77 Se chemical shift, and the product ratios were determined for each reaction. The ratios of azetidine 2 to pyrrolidine 3 increased not only according to the steric hindrance around the alpha-carbon, but also with the nature of the counterion X- (PhSeCl < PhSeBr < PhSeI). Use of PhSeI and amines 1g to 1k (R-1, R-2, not equalH), produced only the azetidinium. salts 2(HI), allowing the isolation of the corresponding azetidines 2, albeit in poor yield. Some reactions were monitored by Se-77 NMR at the beginning of the addition-cyclization process. No intermediates were observed when PhSeI was used, but the thermodynamic addition products 5(Br), 5(HBr), and some dibromose-lenuranes 8 were detected. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
• Diastereoselective Ti-mediated preparation of bicyclic aminocyclopropanes from N-alkenyl amides
  作者：Claire Madelaine、Andrea K. Buzas、Justyna A. Kowalska-Six、Yvan Six、Benoît Crousse

  DOI：10.1016/j.tetlet.2009.07.031

  日期：2009.9

  Intramolecular Ti-mediated alkene-amide couplings of a range of N-alk-3-enyl amides fitted with a substituent at the homoallylic position are described. CF3-substituted compounds are suitable substrates and bicyclic aminocyclopropanes bearing a CF3 group can be prepared in this way. Good diastereoselectivities can be observed depending on the substitution pattern, and best results are obtained in diethyl ether rather than in THF. (C) 2009 Elsevier Ltd. All rights reserved.
• Stereocontrolled Synthesis of 1,2-Dialkyl-4-halopyrrolidines through PhSeX-Induced Cyclization of Secondary Homoallylamines
  作者：Francis Outurquin、Xavier Pannecoucke、Bénédicte Berthe、Claude Paulmier

  DOI：10.1002/1099-0690(200203)2002:6<1007::aid-ejoc1007>3.0.co;2-a

  日期：2002.3