N-4-chlorobenzylhydroxylamine | 51307-68-7

• 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-4-chlorobenzylhydroxylamine
• 英文别名: N-p-chlorobenzylhydroxylamine；p-chlorobenzylhydroxylamine；N-(4-chloro-benzyl)-hydroxylamine；N-(4-Chlor-benzyl)-hydroxylamin；p-Chlorbenzylhydroxylamin；N-[(4-chlorophenyl)methyl]hydroxylamine
• CAS: 51307-68-7
• 化学式: C₇H₈ClNO
• 分子量: 157.6
• InChiKey: BGQHUMGDKKVWMB-UHFFFAOYSA-N

物化性质

• 沸点：
  289.7±42.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-4-chlorobenzylhydroxylamine 在 亚硝酸丁酯 、 氨 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  Synthesis and tyrosinase inhibitory activity of novel N-hydroxybenzyl-N-nitrosohydroxylamines

  摘要：

  Several novel N-substituted N-nitrosohydroxylamines were synthesized. They all inhibited mushroom tyrosinase, but the type of inhibition was different depending on the substituent. Some N-(mono- or dihydroxybenzyl)-N-nitrosohydroxylamines exhibited uncompetitive inhibition with respect to (L)-dopa. Among them, compound 6 was also a competitive inhibitor with respect to oxygen. This observation suggests that another interaction by the meta- or para-hydroxyl group might stabilize the binding of the inhibitor to the enzyme through the oxygen binding site. (C) 2003 Elsevier Science (USA). All rights reserved.

  DOI：

  10.1016/s0045-2068(03)00026-9
• 作为产物：
  描述：

  1-(4-chlorophenyl)-N-trimethylsilyloxymethanamine 在 水 作用下， 生成 N-4-chlorobenzylhydroxylamine
  参考文献：
  名称：

  A novel one-pot reductive amination of aldehydes and ketones with lithium perchlorate and zirconium borohydride–piperazine complexes

  摘要：

  A novel, one-pot reductive mono-alkylation method of amines (primary and secondary), 1,2-phenylenediamine, O-trimethylsilyl-hydroxylamine, and N,N-dimethylhydrazine was developed using LiClO4 (5 mol %) as a source for in situ generation of imine, iminium ion, oxime, and hydrazone, and zirconium borohydride-piperazine complex as reducing agent. This condition is especially useful for situations in which it is not practical to use the amine in excess (as is typically the case under acid-catalyzed conditions) or for acid-sensitive compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.026

文献信息

• Regioselective Asymmetric Formal (3+2) Cycloadditions of Nitrone Ylides from Isatins and Enals
  作者：Yu-Rong Chen、Gu Zhan、Wei Du、Ying-Chun Chen

  DOI：10.1002/adsc.201600805

  日期：2016.12.7

  A highly regio‐, diastereo‐ and enantioselective formal (3+2) cycloaddition reaction of nitrone ylides from isatins and α,β‐unsaturated aldehydes was developed via iminium catalysis in the presence of an additional base, furnishing a spectrum of 1′‐hydroxy‐3,2′‐pyrrolidinylspirooxindole frameworks. Interestingly, the regioselectivity could be finely switched in the reactions between nitrone ylides and

  在另外的碱的存在下，通过亚胺鎓催化作用，开发了高度的区域，非对映体和对映体选择性对映体（3 + 2）的硝基亚硝基化物和α，β-不饱和醛的正环加成反应，提供了1'-羟基的光谱‐3,2'吡咯烷基吡咯并辛醇骨架。有趣的是，通过加入催化量的高氯酸锂和溴化铜（II），可以在硝酰基亚砜和巴豆醛之间的反应中很好地切换区域选择性。
• Highly Enantioselective Intermolecular Hydroamination of Allylic Amines with Chiral Aldehydes as Tethering Catalysts
  作者：Melissa J. MacDonald、Colin R. Hesp、Derek J. Schipper、Marc Pesant、André M. Beauchemin

  DOI：10.1002/chem.201203462

  日期：2013.2.18

  Chirally LinkedIn: Chiral aldehydes are effective tethering catalysts for enantioselective intermolecular hydroamination, which provides access to vicinal diamine motifs in good yields and excellent enantioselectivities (see scheme). This work highlights simple chiral α‐oxygenated aldehydes as effective organocatalysts capable of efficiently inducing asymmetry through transient intramolecularity.

  手性醛：手性醛是对映选择性分子间加氢胺化的有效束缚催化剂，可提供高产率和优异对映选择性的邻位二胺基序（参见方案）。这项工作强调了简单的手性α-氧化醛作为有效的有机催化剂，能够通过瞬态分子内有效诱导不对称性。
• ISOXAZOLIDINE DERIVATIVES
  申请人：Armani Elisabetta

  公开号：US20110065678A1

  公开（公告）日：2011-03-17

  Novel glucocorticosteroids that are derivatives of isoxazolidine are useful as anti-inflammatory and antiallergic compounds.

  新型糖皮质类固醇衍生物异噁唑啉具有抗炎和抗过敏作用。
• Privileged Biorenewable Secologanin‐Based Diversity‐Oriented Synthesis for Pseudo‐Natural Alkaloids: Uncovering Novel Neuroprotective and Antimalarial Frameworks
  作者：Huajian Zhu、Yunrui Cai、Shijia Ma、Yushi Futamura、Jinbiao Li、Wen Zhong、Xiangnan Zhang、Hiroyuki Osada、Hongbin Zou

  DOI：10.1002/cssc.202101868

  日期：2021.12.6

  Diversity win: The chameleon-like behavior of secologanin in nature assures the sustainable, simple, efficient, and enantioselective diversity-oriented synthesis of diverse bioactive non-natural alkaloids.

  多样性获胜：secologanin 在自然界中的变色龙样行为确保了多种生物活性非天然生物碱的可持续、简单、高效和对映选择性的多样性导向合成。
• Direct Asymmetric Aza-Vinylogous-Type Michael Additions of Nitrones from Isatins to Nitroalkenes
  作者：Gu Zhan、Ming-Lin Shi、Wei-Jia Lin、Qin Ouyang、Wei Du、Ying-Chun Chen

  DOI：10.1002/chem.201701290

  日期：2017.5.5

  Nitrones commonly act as 1,3‐dipoles and electrophiles to furnish valuable isoxazolidine and N‐hydroxyl products, respectively. They also can be converted to nitrone ylide species and undergo [3+2] formal cycloadditions to access N‐hydroxyl pyrrolidines. Here, asymmetric direct aza‐vinylogous‐type additions of nitrones from isatins to nitroalkenes are presented, catalyzed by a bifunctional thiourea‐tertiary

  亚硝酸盐通常充当1,3-偶极子和亲电子试剂，分别提供有价值的异恶唑烷和N-羟基产物。它们也可以转化为亚硝基叶立德物质，并经历[3 + 2]正式的环加成反应，从而获得N-羟基吡咯烷。在这里，介绍了一种由双功能素硫脲叔胺催化的从靛红到硝基烯烃的不对称直接氮杂-乙烯基型氮杂加成反应，从而提供具有扩展的碳骨架的高度官能化的硝酮，具有出色的立体选择性。值得注意的是，硝酮部分可以轻松除去，从而提供了烷基胺型物质的形式上不对称的α-官能化。而且，剩余的亲电硝酮基序使得随后的环切反应能够以高分子复杂性和多样性构建螺环产物，这可能在药物发现中具有潜在的应用。