N-(1-isopropyl-3-butenyl)benzylamine | 88381-96-8

• 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: N-(1-isopropyl-3-butenyl)benzylamine
• 英文别名: Benzenemethanamine, N-[1-(1-methylethyl)-3-butenyl]-；N-benzyl-2-methylhex-5-en-3-amine
• CAS: 88381-96-8
• 化学式: C₁₄H₂₁N
• 分子量: 203.327
• InChiKey: ZISSMDFBWGWFPW-UHFFFAOYSA-N

物化性质

• 沸点：
  280.1±19.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-(1-isopropyl-3-butenyl)benzylamine 在 苯基溴化硒 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 以77%的产率得到1-Benzyl-4-bromo-2-isopropyl-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：

  (Z)-N-(2-methylpropylidene)benzylamine 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-(1-isopropyl-3-butenyl)benzylamine
  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

• Indium mediated Barbier-type allylation of aldimines in alcoholic solvents
  作者：Tirayut Vilaivan、Chutima Winotapan、Tetsuro Shinada、Yasufumi Ohfune

  DOI：10.1016/s0040-4039(01)01977-3

  日期：2001.12

  Barbier-type allylation of unactivated aldimines with allyl bromides in the presence of indium powder took place rapidly in alcoholic solvents to give homoallylic amines in fair to good yields.

  在铟粉存在下，未活化的亚胺与烯丙基溴的Barbier型烯丙基化反应在醇类溶剂中迅速发生，从而以均等到良好的收率得到均烯丙基胺。
• 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.
• Asymmetric synthesis of di- and trisubstituted pyrrolidinones via zirconium-mediated intramolecular coupling of N-3-alkenyl carbamates
  作者：Clément Denhez、Jean-Luc Vasse、Dominique Harakat、Jan Szymoniak

  DOI：10.1016/j.tetasy.2007.01.026

  日期：2007.2

  N-3-Alkenyl carbamates, which are readily available in enantiomerically pure form, undergo a stereoselective intramolecular coupling under the effect of a Cp2ZrCl2/2n-BuLi reagent. The influence of the carbamate structure on the stereoselectivity was tested. The reaction gives an easy access to various di-and trisubstituted enantiopure pyrrolidinones. (c) 2007 Elsevier Ltd. All rights reserved.
• Regioselective synthesis of azetidines or pyrrolidines by selenium-induced cyclization of secondary homoallylic amines
  作者：Xavier Franck、Stéphane Leleu、Francis Outurquin

  DOI：10.1016/j.tetlet.2010.06.087

  日期：2010.8

  Azetidines or pyrrolidines can be regioselectively obtained by selenocyclization of homoallylic amines, according to the double bond substitution (C) 2010 Elsevier Ltd All rights reserved