N-Benzyl-N-(1-isopropyl-but-3-enyl)-hydroxylamine | 198694-24-5

• 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-Benzyl-N-(1-isopropyl-but-3-enyl)-hydroxylamine
• 英文别名: N-benzyl-N-(2-methylhex-5-en-3-yl)hydroxylamine
• CAS: 198694-24-5
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: GRPROSVFMYPRSA-UHFFFAOYSA-N

物化性质

• 沸点：
  331.2±31.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-Benzyl-N-(1-isopropyl-but-3-enyl)-hydroxylamine 在 Hoveyda-Grubbs catalyst second generation lutidine 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-5-(benzyl((tert-butyldimethylsilyl)oxy)amino)-6-methylhept-2-en-1-yl acetate
  参考文献：
  名称：

  羟基胺氧在钯 (0)- 和钯 (II)- 催化的烯丙基烷基化中作为亲核试剂：获得异恶唑烷的新途径

  摘要：

  在寻找新的杂环化过程中，描述了高烯丙基羟基胺的分子内 Pd 介导的烯丙基烷基化。根据反应条件和底物，优先获得 CIS-或 TRANS-3-取代的-5-乙烯基异恶唑烷。通过容易获得的未取代的高烯丙基羟胺的交叉复分解反应，很容易获得用于环化步骤的相应起始原料。

  DOI：

  10.1055/s-2007-973868
• 作为产物：
  描述：

  氯丙烯镁 、 (Z)-N-(2-methylpropylidene)benzylamine N-oxide 以 四氢呋喃 为溶剂， 以65%的产率得到N-Benzyl-N-(1-isopropyl-but-3-enyl)-hydroxylamine
  参考文献：
  名称：

  A new route to 3,5-disubstituted isoxazolidines via the iodocyclization of homoallylic hydroxylamines

  摘要：

  N,N-Dialkyl-O-trialkylsilyl homoallylic hydroxylamines reacted with iodine, N-iodosuccinimide, or iodine chloride to give 3,5-disubstituted isoxazolidines in good yield. The relative configuration that was generated at C3 and C5 was controlled by the nature of the nitrogen substituent of the parent hydroxylamine: the presence of a primary alkyl group favored the formation of a cis-isoxazolidine, whereas the presence of a tert-butyl group favored the formation of a trans-isoxazolidine. The effects that the N- and O-substituents and the nature of the iodinating agent exerted on the stereoselectivity of the cyclization were examined. The synthesis of enantiomerically pure isoxazolidines from hydroxylamines carrying a chiral N-mannofuranosyl group is described.

  DOI：

  10.1021/jo00013a032

文献信息

• Stereoselective Synthesis of Pyrrolidines and Pyrrolizidines by Intramolecular Carbolithiation
  作者：Iain Coldham、Richard Hufton、Kathy Price、Richard Rathmell、David Snowden、Graham Vennall

  DOI：10.1055/s-2001-16074

  日期：——

  Methods for the preparation of substituted homoallylic amines and their conversion to pyrrolidines or pyrrolizidines are described. N-Alkylation of a variety of homoallylic secondary amines with (tributylstannyl)methyl methanesulfonate and subsequent tin-lithium exchange, generates organolithium species that undergo intramolecular carbolithiation (anionic cyclization). High stereoselectivities in the cyclization, particularly for the formation of 2,4-disubstituted pyrrolidines, are obtained.

  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。
• Stereoselective Anionic Cyclizations to Pyrrolidines
  作者：Iain Coldham、Richard Hufton、Richard E Rathmell

  DOI：10.1016/s0040-4039(97)01808-x

  日期：1997.10

  Cyclization of alpha-amino-organolithiums onto unactivated alkenes results in the formation of 2,4-disubstituted pyrrolidines with high selectivities in favour of the cis isomers. The use of the alpha-methylbenzyl chiral auxiliary on the nitrogen atom gives rise to 3-substituted pyrrolidines with up to 58% d.e. Without the chiral auxiliary, enantioselectivities in the presence of (-)-sparteine are poor. (C) 1997 Elsevier Science Ltd.
• MANCINI, FABRIZIO;PIAZZA, MARIA GIULIA;TROMBINI, CLAUDIO, J. ORG. CHEM., 56,(1991) N3, C. 4246-4252
  作者：MANCINI, FABRIZIO、PIAZZA, MARIA GIULIA、TROMBINI, CLAUDIO

  DOI：——

  日期：——