N-methyl-N-nitroso-3-benzyloxypropylamine | 663600-22-4

• 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-methyl-N-nitroso-3-benzyloxypropylamine
• 英文别名: N-[3-(Benzyloxy)propyl]-N-methylnitrous amide；N-methyl-N-(3-phenylmethoxypropyl)nitrous amide
• CAS: 663600-22-4
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: QNQCMPUJHARNGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-亚硝基甲基-(3-羟基丙基)胺 、 氯化苄 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 42.33h， 以77%的产率得到N-methyl-N-nitroso-3-benzyloxypropylamine
  参考文献：
  名称：

  New Simple Polymeric Supports with Hydrazone Linkers for Solid-Phase Synthesis of Ketones and Primary Amines

  摘要：

  本文描述了带有肼固定基团的新型固体载体的制备及其在酮和伯胺固相合成中的应用。这些载体用于酮类的固定化，包括4-叔丁基环己酮、戊-3-酮、丙酮、N-甲基哌啶酮、N-苄基哌啶酮和托品酮，形成它们的腙形式。聚合物支持的腙经过一次或两次的去质子化/烷基化过程（LDA/RX）。所得的烷基化产物在四氢呋喃中用三氟乙酸处理后从固体载体上脱离，生成α-烷基化或α,α′-双烷基化酮，或在四氢呋喃中用硼烷进行还原裂解，得到β-烷基化或β,β′-双烷基化伯胺。

  DOI：

  10.1055/s-2003-42483

文献信息

• Application of Piperazine-Derived Hydrazone Linkers for Alkylation of Solid-Phase Immobilized Ketones
  作者：Ryszard Lazny、Michal Michalak

  DOI：10.1055/s-2002-34879

  日期：——

  The preparation and application of three new solid supports with piperazine-derived hydrazine anchoring groups are described. The supports were used for immobilization of ketones. The ketones: cyclohexanone, 4-tert-butylcyclohexanone, 3-pentanone and tropinone, which were bound to polymers in the form of their hydrazones, were deprotonated with LDA and alkylated with propyl iodide or benzyl bromide. The resulting alkylated products were cleaved off the solid support on treatment with trifluoroacetic acid in dichloromethane. Linkers with 6- and 3-carbon atom spacers gave better results than the simple N-aminopiperazine linker.

  本文描述了三种新型固体支架的制备和应用，这些支架具有源自哌嗪的肼锚定基团。所述支架用于酮的固定化。酮包括环己酮、4-叔丁基环己酮、3-戊酮和托品酮，这些酮以肼酮的形式与聚合物结合，经过LDA去质子化后，用丙基碘或苄基溴进行烷基化。得到的烷基化产物用三氟乙酸在二氯甲烷中处理后从固体支架上断裂。具有6个和3个碳原子间隔的连接器效果优于简单的N-氨基哌嗪连接器。
• New Simple Polymeric Supports with Hydrazone Linkers for Solid-Phase Synthesis of Ketones and Primary Amines
  作者：Ryszard Lazny、Aneta Nodzewska、Karol Wolosewicz

  DOI：10.1055/s-2003-42483

  日期：——

  The preparation of new solid supports with hydrazine anchoring groups and their application to solid-phase synthesis of ketones and primary amines are described. The supports were used for immobilization of ketones, 4-tert-butylcyclohexanone, pentan-3-one, acetone, N-methylpiperidone, N-benzylpiperidone, and tropinone in the form of their hydrazones. The polymer-supported hydrazones were subjected to deprotonation/alkylation procedure (LDA/RX) once or twice. The resulting alkylated products were cleaved off the solid support on treatment with trifluoroacetic acid in tetrahydrofuran providing α-alkylated or α,α′-bisalkylated ketones or were subjected to reductive cleavage with borane in tetrahydrofuran to give β-alkylated or β,β′-bisalkylated primary amines.

  本文描述了带有肼固定基团的新型固体载体的制备及其在酮和伯胺固相合成中的应用。这些载体用于酮类的固定化，包括4-叔丁基环己酮、戊-3-酮、丙酮、N-甲基哌啶酮、N-苄基哌啶酮和托品酮，形成它们的腙形式。聚合物支持的腙经过一次或两次的去质子化/烷基化过程（LDA/RX）。所得的烷基化产物在四氢呋喃中用三氟乙酸处理后从固体载体上脱离，生成α-烷基化或α,α′-双烷基化酮，或在四氢呋喃中用硼烷进行还原裂解，得到β-烷基化或β,β′-双烷基化伯胺。