N-benzyl-N-octylhydroxylamine | 139633-09-3

• 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-octylhydroxylamine
• CAS: 139633-09-3
• 化学式: C₁₅H₂₅NO
• 分子量: 235.37
• InChiKey: PIFZTGRYAOVBJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  357.7±21.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-octylhydroxylamine 在 ~ 5 mol% gold on silica 作用下， 以 水 为溶剂， 反应 16.0h， 以47%的产率得到N-octyl-N-phenylmethyleneamine N-oxide
  参考文献：
  名称：

  负载在二氧化硅上的金催化 N,N-二取代羟胺有氧氧化成硝酮

  摘要：

  通过探索负载在二氧化硅上的金的新催化反应性，开发了一种通过相应 N,N-二取代羟胺的有氧氧化制备硝酮的新方法。氧化发生在非常温和的条件下（空气、甲醇或水的流量，室温）。一系列高度官能化的羟胺的氧化具有完全的转化率和出色的硝酮产率，说明了这种实用方法的选择性、效率和可靠性。在与苯甲醇和二丁胺的竞争实验中，氧化显示化学选择性地发生。

  DOI：

  10.1002/ejoc.201501001
• 作为产物：
  描述：

  α-Heptyl-N-benzylnitrone 在 lithium aluminium tetrahydride 、 臭氧 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-benzyl-N-octylhydroxylamine
  参考文献：
  名称：

  Synthesis and x-ray analysis of dihydro-1,2,4,5-trioxazine. Evidence of a stepwise mechanism for the [3 + 3] cycloaddition of carbonyl oxides with nitrones

  摘要：

  Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo [3 + 3] cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield. The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis. Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-alpha-(4-methylphenyl)-alpha-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts. This result, in conjunction with the structure of the relevant 5t, suggests that the [3 + 3] cycloaddition proceeds by a stepwise mechanism.

  DOI：

  10.1021/jo00034a018

文献信息

• A NOVEL METHOD FOR THE PREPARATION OF PRIMARY AMINES BY THE USE OF<i>N</i>-BENZYLHYDROXYLAMINE AND 2-FLUOROPYRIDINIUM SALT
  作者：Teruaki Mukaiyama、Takashi Tsuji、Yutaka Watanabe

  DOI：10.1246/cl.1978.1057

  日期：1978.10.5

  Primary amines were prepared from alkyl halides or olefinic compounds by the use of N-benzylhydroxylamine and 2-fluoro-1-methylpyridinium p-toluenesulfonate.

  通过使用 N-苄基羟胺和 2-氟-1-甲基吡啶鎓对甲苯磺酸盐，从烷基卤化物或烯烃化合物制备伯胺。
• Oxidation of <i>N</i>,<i>N</i>-Disubstituted Hydroxylamines to Nitrones with Hypervalent Iodine Reagents
  作者：Camilla Matassini、Camilla Parmeggiani、Francesca Cardona、Andrea Goti

  DOI：10.1021/acs.orglett.5b02029

  日期：2015.8.21

  Hypervalent iodine compounds are viable reagents for the oxidation of N,N-disubstituted hydroxylamines to the corresponding nitrones, with IBX performing best. The procedure is very simple and user-friendly and affords the target compounds with high efficiency and regioselectivity, highlighting IBX as the reagent of choice for preparation of aldonitrones from nonsymmetric hydroxylamines. Evidence for

  高价碘化合物是将N，N-二取代的羟胺氧化为相应的硝酮的可行试剂，而IBX表现最佳。该方法非常简单且易于使用，可为目标化合物提供高效和区域选择性，突出了IBX作为从非对称羟胺制备醛酮的选择试剂。已经收集了涉及氮与碘配位的机理的证据。
• Diruthenium Diacetate Catalysed Aerobic Oxidation of Hydroxylamines and Improved Chemoselectivity by Immobilisation to Lysozyme
  作者：Flavia Lupi、Tiziano Marzo、Giampiero D'Adamio、Sara Cretella、Francesca Cardona、Luigi Messori、Andrea Goti

  DOI：10.1002/cctc.201701083

  日期：2017.11.23

  A new green method for the preparation of nitrones through the aerobic oxidation of the corresponding N,N‐disubstituted hydroxylamines has been developed upon exploring the catalytic activity of a diruthenium catalyst, that is, [Ru2(OAc)4Cl]), in aqueous or alcoholic solution under mild reaction conditions (0.1 to 1 mol % catalyst, air, 50 °C) and reasonable reaction times. Notably, the catalytic activity

  通过探索二钌催化剂的催化活性，即[Ru 2（OAc）4 Cl]），开发了一种新的绿色方法，该方法通过相应的N，N-二取代羟胺的需氧氧化来制备硝酮。水溶液或酒精溶液，反应条件温和（0.1至1 mol％的催化剂，空气，50°C）和合理的反应时间。值得注意的是，双金属中心与小蛋白溶菌酶结合后，其催化活性得以保留。有趣的是，与二钌催化剂相比，这种新的人工金属酶赋予了对环羟胺氧化的完全化学选择性。
• Synthesis and x-ray analysis of dihydro-1,2,4,5-trioxazine. Evidence of a stepwise mechanism for the [3 + 3] cycloaddition of carbonyl oxides with nitrones
  作者：Mitsuyuki Mori、Tomohito Sugiyama、Masatomo Nojima、Shigekazu Kusabayashi、Kevin J. McCullough

  DOI：10.1021/jo00034a018

  日期：1992.4

  Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo [3 + 3] cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield. The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis. Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-alpha-(4-methylphenyl)-alpha-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts. This result, in conjunction with the structure of the relevant 5t, suggests that the [3 + 3] cycloaddition proceeds by a stepwise mechanism.
• Gold Supported on Silica Catalyzes the Aerobic Oxidation of<i>N</i>,<i>N</i>-Disubstituted Hydroxylamines to Nitrones
  作者：Giampiero D'Adamio、Camilla Parmeggiani、Andrea Goti、Francesca Cardona

  DOI：10.1002/ejoc.201501001

  日期：2015.9

  A new method for the preparation of nitrones through the aerobic oxidation of the corresponding N,N-disubstituted hydroxylamines has been developed by exploring a new catalytic reactivity of gold supported on silica. The oxidation occurs under very mild conditions (flux of air, methanol or water, room temperature). The oxidation of a range of highly functionalized hydroxylamines with complete conversions

  通过探索负载在二氧化硅上的金的新催化反应性，开发了一种通过相应 N,N-二取代羟胺的有氧氧化制备硝酮的新方法。氧化发生在非常温和的条件下（空气、甲醇或水的流量，室温）。一系列高度官能化的羟胺的氧化具有完全的转化率和出色的硝酮产率，说明了这种实用方法的选择性、效率和可靠性。在与苯甲醇和二丁胺的竞争实验中，氧化显示化学选择性地发生。