N-(对甲基苄基)-O-苄基羟胺 | 5555-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(对甲基苄基)-O-苄基羟胺
• 英文名称: N-(p-methylbenzyl)-O-benzylhydroxylamine
• 英文别名: O-benzyl-N-(4-methylbenzyl)hydroxylamine；1-(4-methylphenyl)-N-phenylmethoxymethanamine
• CAS: 5555-55-5
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: NDMBFTLGAVMDAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  D-葡萄糖 、 N-(对甲基苄基)-O-苄基羟胺 以 甲醇 、 氯仿 、 溶剂黄146 为溶剂， 反应 48.0h， 以67%的产率得到O-benzyl-N-(4-methylbenzyl)-N-(β-D-glucosyl)-hydroxylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of RON-neoglycosides as tumor cytotoxins

  摘要：

  Cardenolides such as digitoxin have been shown to inhibit cancer cell growth, to reduce cancer metastasis, and to induce apoptosis in tumor cells. Among the most potent digitoxin-based cytotoxins identified to date are MeON-neoglycosides generated via oxyamine neoglycosylation. Here, we report our studies of oxyamine neoglycosylation aimed at facilitating the elucidation of linkage-diversified digitoxin neoglycoside structure-activity relationships. We identified conditions suitable for the convenient synthesis of digitoxin neoglycosides and found that sugar structure, rather than RON-glycosidic linkage, exerts the strongest influence on neoglycoside yield and stereochemistry. We synthesized a library of digitoxin neoglycosides and assessed their cytotoxicity against eight human cancer cell lines. Consistent with previous findings, our data show that the structure of RON-neoglycosidic linkages influences both the potency and selectivity of digitoxin neoglycosides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.019
• 作为产物：
  描述：

  苄氧基胺盐酸盐 在 吡啶 、 盐酸 、 吡啶硼烷 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 26.5h， 生成 N-(对甲基苄基)-O-苄基羟胺
  参考文献：
  名称：

  Synthesis and biological evaluation of RON-neoglycosides as tumor cytotoxins

  摘要：

  Cardenolides such as digitoxin have been shown to inhibit cancer cell growth, to reduce cancer metastasis, and to induce apoptosis in tumor cells. Among the most potent digitoxin-based cytotoxins identified to date are MeON-neoglycosides generated via oxyamine neoglycosylation. Here, we report our studies of oxyamine neoglycosylation aimed at facilitating the elucidation of linkage-diversified digitoxin neoglycoside structure-activity relationships. We identified conditions suitable for the convenient synthesis of digitoxin neoglycosides and found that sugar structure, rather than RON-glycosidic linkage, exerts the strongest influence on neoglycoside yield and stereochemistry. We synthesized a library of digitoxin neoglycosides and assessed their cytotoxicity against eight human cancer cell lines. Consistent with previous findings, our data show that the structure of RON-neoglycosidic linkages influences both the potency and selectivity of digitoxin neoglycosides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.019

文献信息

• N-nitrosohydroxylamines I. Acetolysis and acid-catalyzed hydrolysis of N,O-dibenzyl-N-nitrosohydroxylamines. Reaction with potassium t-butoxide
  作者：Kunio Kano、Jean-Pierre Anselme

  DOI：10.1016/s0040-4020(01)89037-2

  日期：——

  more forcing conditions, products of the further hydrolysis of 6 are obtained. Acetolysis in acetic acid gives the benzyl acetates derived from both N- and O-substituents. With potassium tert-butoxide, the major path is abstraction of an O-benzyl hydrogen followed by fragmentation to the aldehyde and the benzyldiazotate ion. Possible mechanisms for the formation of the products are discussed.

  的N，O-二苄基-N- nitrosohydroxylamines（水解的主要产物3）是denitrosated父羟胺（6）; 在更强的条件下，获得了进一步水解6的产物。在乙酸中的乙酸水解得到衍生自N-和O-取代基的乙酸苄酯。对于叔丁醇钾，主要途径是提取O-苄基氢，然后裂解成醛和苄二重氮根离子。讨论了形成产物的可能机制。
• Synthesis of <i>N</i>-alkoxy amines and hydroxylamines <i>via</i> the iridium-catalyzed transfer hydrogenation of oximes
  作者：Yanping Xia、Sen Wang、Rui Miao、Jianhua Liao、Lu Ouyang、Renshi Luo

  DOI：10.1039/d2ob01084d

  日期：——

  hydrogenation of oximes to access N-alkoxy amines and hydroxylamines, and the reaction was accelerated by trifluoroacetic acid. The practical application of this protocol was demonstrated by a gram-scale transformation and two-step synthesis of the fungicide furmecyclox (BAS 389F) in overall yields of 92 and 85%, respectively. An asymmetric protocol using chiral Ir complexes to afford chiral N-alkoxy amines was

  发现阳离子铱（Ir）配合物催化肟的转移加氢以得到N-烷氧基胺和羟胺，并且三氟乙酸加速了反应。该协议的实际应用通过克级转化和杀菌剂 furmecyclox (BAS 389F) 的两步合成得到证明，总产量分别为 92% 和 85%。证明了使用手性 Ir 配合物提供手性N-烷氧基胺的不对称方案，但获得的低产率/ee 表明需要进一步开发。
• Nickel-Catalyzed Double Deoxygenative C–N Coupling of Acyloxyamines
  作者：Kashif Ali、Eun Jin Cho

  DOI：10.1021/acs.orglett.4c01758

  日期：2024.6.21

  activation. The C–N bond formation under mild reaction conditions, employing NiCl2 as the catalyst and cataCXiumA as a ligand, results in the production of a diverse array of alkylated secondary or tertiary amines, including heterocyclic amines. This method introduces a novel catalytic strategy that emphasizes the versatility of nickel-catalyzed reactions, extending beyond traditional synthetic boundaries

  通过使用酰氧基胺通过 N-O 键激活，开发了双脱氧 C-N 偶联方案。使用 NiCl 2作为催化剂和 cataCXiumA 作为配体，在温和的反应条件下形成 C-N 键，产生多种烷基化仲胺或叔胺，包括杂环胺。该方法引入了一种新颖的催化策略，强调镍催化反应的多功能性，超越了传统的合成界限。
• US4696964A
  申请人：——

  公开号：US4696964A

  公开（公告）日：1987-09-29