N-羟基-2-萘胺 | 613-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-羟基-2-萘胺
• 英文名称: β-naphthylhydroxylamine
• 英文别名: N-hydroxy-2-naphthylamine；N-naphthalen-2-ylhydroxylamine
• CAS: 613-47-8
• 化学式: C₁₀H₉NO
• mdl: MFCD01722055
• 分子量: 159.188
• InChiKey: JGXYZXHJZJYHPW-UHFFFAOYSA-N

物化性质

• 熔点：
  136°C (rough estimate)
• 沸点：
  284.68°C (rough estimate)
• 密度：
  1.1202 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

ADMET

代谢

N-羟基-2-萘胺是2-萘胺的人类已知代谢物。

N-Hydroxy-2-naphthalenamine is a known human metabolite of 2-naphthylamine.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  N-羟基-2-萘胺 在 三乙胺 作用下， 以 乙醚 、 乙醇 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 2-amino-8-(2-aminonaphthalen-1-yl)-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
  参考文献：
  名称：

  Synthesis of N-acetoxy-2-aminonaphthaline, an ultimate carcinogen of the carcinogenic 2-naphthylamine, and its reactions with (bio)nucleophiles

  摘要：

  DOI：

  10.1016/s0040-4039(00)95190-6
• 作为产物：
  描述：

  2-硝基萘 在 5% rhodium-on-charcoal 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 N-羟基-2-萘胺
  参考文献：
  名称：

  通过芳基羟胺与芳基锍盐的 SNAr 合成功能化联芳基化合物的无过渡金属级联方法

  摘要：

  我们报告了一种无过渡金属方案，用于通过芳基羟胺到芳基锍盐的亲核芳族取代 (S N Ar) 合成功能化联芳基化合物。使用该协议，结构多样的功能化联芳基以中等至良好的产量顺利获得。这种转化的优点包括反应条件温和、底物范围广、官能团耐受性好、一锅法的可行性以及易于处理和放大。

  DOI：

  10.1021/acs.joc.2c00990

文献信息

• Cascade Approach to Highly Functionalized Biaryls by a Nucleophilic Aromatic Substitution with Arylhydroxylamines
  作者：Lirong Guo、Fengting Liu、Liying Wang、Hairui Yuan、Lei Feng、László Kürti、Hongyin Gao

  DOI：10.1021/acs.orglett.9b00927

  日期：2019.4.19

  A transition-metal free synthesis of highly functionalized 2-hydroxy-2′-amino-1,1′-biaryls from N-arylhydroxylamines has been developed. This operationally simple and readily scalable approach relies on a cascade of reactions that initially generates transient N,O-diarylhydroxylamines, via direct O-arylation, which then undergo rapid [3,3]-sigmatropic rearrangement and subsequent rearomatization to

  已经开发了由N-芳基羟胺合成的无过渡金属的高官能化2-羟基-2'-氨基-1,1'-联芳基。这种操作简单且易于扩展的方法依赖于一连串的反应，这些反应最初通过直接的O-芳基化反应生成N，O-二芳基羟胺，然后进行快速的[3,3]-σ重排，然后重新进行芳构化，形成NOBIN型产物。这些结构多样的官能化联芳基是在温和的条件下以良好或优异的分离收率得到的。
• Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides
  作者：Yuanbo Du、Zhenguo Xi、Lirong Guo、Haifeng Lu、Lei Feng、Hongyin Gao

  DOI：10.1016/j.tetlet.2021.153074

  日期：2021.5

  thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho CH bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this

  这项工作证明了一种从容易获得的芳羟胺和亚硫酰溴合成邻溴代苯胺的简便方法。在本文的反应中使用了温和的反应条件和从杂环结构到药物潜在基序的广泛底物范围。已经实现了对羟基胺的邻位C H键的有效溴化。以高至极好的收率获得了邻溴代苯胺产品，并且在这项工作中显示了这种合成方法的模型放大反应。
• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：Obrecht Daniel

  公开号：US20120270881A1

  公开（公告）日：2012-10-25

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of formulae Ia and Ib are constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. These macrocycles Ia and Ib are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being the agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), ion channels and signal transduction pathways. In particular, these macrocycles act as antagonists of the motilin receptor, the FP receptor and the purinergic receptors P2Y 1 , as modulators of the serotonin receptor of subtype 5-HT 2B , as blockers of the voltage-gated potassium channel K v 1.3 and as inhibitors of the β-catenin-dependent “canonical” Wnt pathway. Thus they are showing great potential as medicaments for a variety of diseases.

  具有结构限制的、空间定义的12-30环的大环系统Ia和Ib由三个不同的分子部分构成：模板A、构象调节剂B和桥C。这些大环Ia和Ib可以通过并行合成或溶液中或固相上的组合化学来轻松制备。它们被设计用于与各种特定的生物靶标类相互作用，例如对G蛋白偶联受体（GPCRs）、离子通道和信号转导途径的激动或拮抗活性。特别地，这些大环作为莫蒂林受体的拮抗剂、FP受体和嘌呤受体P2Y1的调节剂、5-HT2B亚型的5-羟色胺受体的调节剂、电压门控钾通道Kv1.3的阻断剂以及β-连环蛋白依赖的“经典”Wnt途径的抑制剂。因此，它们显示出作为各种疾病药物的巨大潜力。
• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES ET À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2013139697A1

  公开（公告）日：2013-09-26

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1 ) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义明确的大环环形系统由三个不同的分子部分构成：模板A、构象调制剂B和桥梁C。由该环系统I描述的大环可通过溶液中的并行合成或组合化学，或者在固相上制造。它们被设计用来与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，对酶的抑制活性或抗菌活性。特别是，这些大环显示对第1亚型内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃肽3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。
• Direct Construction of <scp>NOBINs</scp> <i>via</i> Domino Arylation and Sigmatropic Rearrangement Reactions
  作者：Ji‐Wei Zhang、Liang‐Wen Qi、Shaoyu Li、Shao‐Hua Xiang、Bin Tan

  DOI：10.1002/cjoc.202000358

  日期：2020.12

  Privileged 2‐amino‐2’‐hydroxy‐1,1’‐binaphthyl (NOBIN) frameworks were constructed through a novel domino arylation of naphthylhydroxylamines with diarylhalonium salts and sigmatropic rearrangement in a transition metal‐free fashion. This protocol bears broad substrate generality and proceeds under mild reaction conditions, affording diversified NOBINs in high efficiency with absolute regiocontrol during the

  通过萘基羟胺与二芳基hal盐的新型多米诺芳基化和无过渡金属的σ重排，构建了优先的2-氨基-2'-羟基-1,1'-联萘（NOBIN）骨架。该方案具有广泛的底物通用性，可在温和的反应条件下进行，可在重排过程中以绝对的区域控制高效提供多样化的NOBIN。旋光性产物可通过一锅中手性N杂环卡宾催化的动力学拆分或由可移动手性助剂引导的非对映选择性[3,3]重排获得。值得注意的是，在组装这种代表性的联芳基骨架时，二芳基氯鎓盐和二芳基溴化salts盐首次被用作芳基化试剂。