(+/-)-N-phenyl-N-(1-phenylbut-3-enyl)hydroxylamine | 322407-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - N-苯基羟胺
• 英文名称: (+/-)-N-phenyl-N-(1-phenylbut-3-enyl)hydroxylamine
• 英文别名: N-phenyl-N-(1-phenylbut-3-enyl)hydroxylamine
• CAS: 322407-22-7
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: CEUYZMYSGYWYCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-phenyl-N-(1-phenylbut-3-enyl)hydroxylamine 在 Hoveyda-Grubbs catalyst second generation 1,4-diacetoxy-but-2-ene 作用下， 生成 phenyl-(1-phenyl-but-3-enyl)-amine
  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：

  N-(benzylidene)aniline N-oxide 、 烯丙基溴化镁 在 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 2.5h， 以88%的产率得到(+/-)-N-phenyl-N-(1-phenylbut-3-enyl)hydroxylamine
  参考文献：
  名称：

  Influence of Hydroxylamine Conformation on Stereocontrol in Pd-Catalyzed Isoxazolidine-Forming Reactions

  摘要：

  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.

  DOI：

  10.1021/jo8027399

文献信息

• Microwave-induced organometallic reactions in aqueous media. Use of Ga and Bi for the allylation of aromatic N-oxides and hydrazones
  作者：Dhrubojyoti D. Laskar、Mukut Gohain、Dipak Prajapati、Jagir S. Sandhu

  DOI：10.1039/b108525p

  日期：2002.2.11

  Homoallylic hydroxylamines and homoallylic hydrazides were synthesised in excellent yields by the reaction of allylgallium or allylbismuth reagent, generated in situ in the presence of 0.1 equivalent of NH4Cl–Bu4NBr, with aldonitrones and hydrazones in aqueous media. The reaction rate can be increased dramatically under microwave activation.

  烯丙基镓或烯丙基铋试剂在 0.1 等量的 NH4Cl-Bu4NBr 存在下原位生成，在水介质中与醛酮和肼反应合成了均烯丙基羟胺和均烯丙基肼，产量极高。在微波活化条件下，反应速率可显著提高。
• Indium mediated allylation of CN compounds in aqueous media
  作者：H.M Sampath Kumar、S Anjaneyulu、E Jagan Reddy、J.S Yadav

  DOI：10.1016/s0040-4039(00)01676-2

  日期：2000.11
• Organometallic reaction in aqueous media. A samarium induced, efficient, synthesis of homoallyl hydroxylamines and hydrazides
  作者：Dhrubojyoti D Laskar、Dipak Prajapati、Jagir S Sandhu

  DOI：10.1016/s0040-4039(01)01637-9

  日期：2001.10

  Samarium can be used directly for the allylation of aldonitrones and hydrazones in aqueous media in the presence of Bu4NBr. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.
• 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。