N-benzyl-N-(1-phenylbut-3-enyl)hydroxylamine | 887239-61-4

• 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: N-benzyl-N-(1-phenylbut-3-enyl)hydroxylamine
• CAS: 887239-61-4
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: XJKKIXXYVLYZCD-UHFFFAOYSA-N

物化性质

• 熔点：
  53-54 °C
• 沸点：
  405.8±44.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-(1-phenylbut-3-enyl)hydroxylamine 在 copper diacetate 、 溶剂黄146 、 锌 作用下， 反应 1.0h， 以0.21 g的产率得到N-苄基-1-苯基-3-丁烯-1-胺
  参考文献：
  名称：

  D-葡萄糖衍生的 γ-链烯胺与汞 (II) 盐的 5-Endo-trig 环化：1-Deoxycastanospermine 及其 8a-epi-类似物的合成†

  摘要：

  γ-链烯基胺 1a、1b 和 4 的分子内氨基汞化显示仅以良好的产率提供 5-endo-trig 环化产物。由此从 D-葡萄糖衍生的 γ-链烯基胺 1a 和 1b 获得的吡咯烷衍生物的效用在 1-脱氧栗精胺 (3a) 和 1-脱氧-8a-epi-栗精胺 (3b) 的合成中得到证明。

  DOI：

  10.3390/10080893
• 作为产物：
  描述：

  N-Benzylidenebenzylamine N-oxide 、 烯丙基溴化镁 以 四氢呋喃 为溶剂， 反应 1.0h， 以39%的产率得到N-benzyl-N-(1-phenylbut-3-enyl)hydroxylamine
  参考文献：
  名称：

  通过Pd催化的N-丁烯基羟胺的碳醚化立体选择性合成异恶唑烷。

  摘要：

  DOI：

  10.1002/anie.200701386

文献信息

• Hydroxylamine Oxygen as Nucleophile in Palladium(0)- and Palladium(II)-Catalyzed Allylic Alkylation: A Novel Access to Isoxazolidines
  作者：Pedro Merino、Giovanni Poli、Tomas Tejero、Vanni Mannucci、Guillaume Prestat、David Madec

  DOI：10.1055/s-2007-973868

  日期：2007.4

  In search for novel heterocyclization processes, the intramolecular Pd-mediated allylic alkylation of homoallyl hydroxyl-amines is described. Depending on both the reaction conditions and the substrates, CIS- or TRANS-3-substituted-5-vinyl isoxazolidines are preferentially obtained. The corresponding starting materials for the cyclization step are readily obtained through cross-metathesis of the easily

  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。
• Influence of Hydroxylamine Conformation on Stereocontrol in Pd-Catalyzed Isoxazolidine-Forming Reactions
  作者：Georgia S. Lemen、Natalie C. Giampietro、Michael B. Hay、John P. Wolfe

  DOI：10.1021/jo8027399

  日期：2009.3.20

  Palladium-catalyzed carboamination reactions between N-Boc-O-(but-3-enyl)hydroxylamine derivatives and aryl or alkenyl bromides afford cis-3,5- and trans-4,5-disubstituted isoxazolidines in good yield with up to >20:1 dr. The diastercoselectivity observed in the formation of cis-3,5-disubstituted isoxazolidines is superior to selectivities typically obtained in other transformations, such as 1,3-dipolar cycloaddition reactions, that provide these products. In addition, the stereocontrol in the C-N bond-forming Pd-catalyzed carboamination reactions of N-Boc-O-(but-3-enyl)hydroxylamines is significantly higher than that of related C-O bond-forming carboetherification reactions of N-benzyl-N-(but-3-enyl)hydroxylamine derivatives. This is likely due to a stereoelectronic preference for cyclization via transition states in which the Boc group is placed in a perpendicular orientation relative to the plane of the developing ring, which derives from the conformational equilibria of substituted hydroxylamines.
• Stereoselective Synthesis of Isoxazolidines through Pd-Catalyzed Carboetherification ofN-Butenylhydroxylamines
  作者：Michael B. Hay、John P. Wolfe

  DOI：10.1002/anie.200701386

  日期：2007.8.27
• A new route to 3,5-disubstituted isoxazolidines via the iodocyclization of homoallylic hydroxylamines
  作者：Fabrizio Mancini、Maria Giulia Piazza、Claudio Trombini

  DOI：10.1021/jo00013a032

  日期：1991.6

  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.
• 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：——