N-benzyloxycarbonyl-4-nitrophenethylamine | 182252-00-2

• 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-benzyloxycarbonyl-4-nitrophenethylamine
• 英文别名: benzyl 4-nitrophenethylcarbamate；4-nitrophenylethylcarbamic acid benzyl ester；benzyl N-[2-(4-nitrophenyl)ethyl]carbamate
• CAS: 182252-00-2
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: CRYZSMNZLSDLBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-4-nitrophenethylamine 在 甲酸铵 、 锌 作用下， 以 甲醇 为溶剂， 以97 %的产率得到benzyl 4-aminophenethylcarbamate
  参考文献：
  名称：

  4-(2,6-二甲基-3-硝基吡啶-4-基氨基)苯乙基氨基甲酸苄基酯的制备方法

  摘要：

  本发明涉及药物技术领域，具体提供一种4‑(2,6‑二甲基‑3‑硝基吡啶‑4‑基氨基)苯乙基氨基甲酸苄基酯的制备方法。以4‑硝基苯乙胺盐酸盐(SM‑1)为起始原料，将其与氯甲酸苄酯反应，得到4‑硝基苯乙基氨基甲酸苄基酯(G‑1a)；G‑1a再通过硝基还原得到4‑氨基苯乙基氨基甲酸苄基酯(G‑1b)；G‑1b与4‑氯‑2,6‑二甲基‑3‑硝基吡啶通过亲核取代反应最终得到Gra‑1。该方案简便易行，成本低同时产物收率和纯度高，适于工业化生产。

  公开号：

  CN117800905A
• 作为产物：
  描述：

  苄氧羰基氨基乙基三氟硼酸钾 、 1-溴-4-硝基苯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 caesium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 12.0h， 以84%的产率得到N-benzyloxycarbonyl-4-nitrophenethylamine
  参考文献：
  名称：

  Scope of the Suzuki−Miyaura Aminoethylation Reaction Using Organotrifluoroborates

  摘要：

  Potassium beta-aminoethyltrifluoroborates were prepared in good yields via hydroboration of the corre- sponding enecarbamates using the Snieckus hydroborating reagent. A wide variety of phenethylamines containing a potentially free primary amine after appropriate deprotection have been successfully prepared in good yield using these organotrifluoroborates as partners in Suzuki-Miyaura coupling with aryl bromides, iodides, and triflates.

  DOI：

  10.1021/jo7015955

文献信息

• METHOD FOR PRODUCING AROMATIC AMINE COMPOUND
  申请人：Nissan Chemical Industries, Ltd.

  公开号：EP3246308A1

  公开（公告）日：2017-11-22

  To provide a novel method for simply and efficiently removing a Sn compound contained in a reaction liquid at the time of reducing an aromatic nitro compound as a starting material with stannous chloride to produce an aromatic amine compound. A method for producing an aromatic amine compound represented by the formula 2, which comprises reducing an aromatic nitro compound represented by the formula 1 (Ar is an aromatic group) with stannous chloride, wherein a reaction liquid obtained by reducing the aromatic nitro compound represented by the formula 1, is brought into contact with a mixed liquid containing a compound having a benzene ring and a potassium hydroxide aqueous solution to carry out liquid separation, and from the obtained organic layer, the aromatic amine compound represented by the formula 2 is obtained:

  提供一种新方法，用于在用氯化锡还原作为起始原料的芳香族硝基化合物以生产芳香族胺 化合物时，简单而有效地除去反应液中所含的 Sn 化合物。 一种生产式 2 所代表的芳香族胺化合物的方法，它包括用氯化亚锡还原式 1 所代表的芳香族硝基化合物（Ar 为芳香族基团），其中还原式 1 所代表的芳香族硝基化合物得到的反应液与含有苯环化合物和氢氧化钾水溶液的混合液接触，进行液体分离，从得到的有机层中得到式 2 所代表的芳香族胺化合物：
• Pd/C(en)-Catalyzed Chemoselective Hydrogenation with Retention of the N-Cbz Protective Group and its Scope and Limitations
  作者：Kazuyuki Hattori、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/s0040-4020(00)00771-7

  日期：2000.10

  A chemoselective method for the hydrogenation of acetylene, olefin, azide, nitro and benzyl ester functionalities with retention of the aliphatic N-Cbz group was established. The chemoselectivity was accomplished by using a combination of 5% Pd/C-ethylenediamine [5% Pd/C(en)] and THF (or 1,4-dioxane) as a solvent, and the scope and limitations of this methodology were investigated. These results reinforce the utility of N-Cbz protective groups in synthetic chemistry, especially in peptide synthesis (C) 2000 Elsevier Science Ltd. All lights reserved.
• Scope of the Suzuki−Miyaura Aminoethylation Reaction Using Organotrifluoroborates
  作者：Gary A. Molander、Ludivine Jean-Gérard

  DOI：10.1021/jo7015955

  日期：2007.10.1

  Potassium beta-aminoethyltrifluoroborates were prepared in good yields via hydroboration of the corre- sponding enecarbamates using the Snieckus hydroborating reagent. A wide variety of phenethylamines containing a potentially free primary amine after appropriate deprotection have been successfully prepared in good yield using these organotrifluoroborates as partners in Suzuki-Miyaura coupling with aryl bromides, iodides, and triflates.
• 4-(2,6-二甲基-3-硝基吡啶-4-基氨基)苯乙基氨基甲酸苄基酯的制备方法
  申请人：洛阳惠中兽药有限公司

  公开号：CN117800905A

  公开（公告）日：2024-04-02

  本发明涉及药物技术领域，具体提供一种4‑(2,6‑二甲基‑3‑硝基吡啶‑4‑基氨基)苯乙基氨基甲酸苄基酯的制备方法。以4‑硝基苯乙胺盐酸盐(SM‑1)为起始原料，将其与氯甲酸苄酯反应，得到4‑硝基苯乙基氨基甲酸苄基酯(G‑1a)；G‑1a再通过硝基还原得到4‑氨基苯乙基氨基甲酸苄基酯(G‑1b)；G‑1b与4‑氯‑2,6‑二甲基‑3‑硝基吡啶通过亲核取代反应最终得到Gra‑1。该方案简便易行，成本低同时产物收率和纯度高，适于工业化生产。