(S)-N-BOC-1-苯乙胺 | 147169-48-0

• 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: (S)-N-BOC-1-苯乙胺
• 英文名称: (S)-tert-butyl 1-phenylethylcarbamate
• 英文别名: (S)-N-(tert-butyloxycarbonyl)-α-methylbenzylamine；(S)-(1-phenyl-ethyl)-carbamic acid tert-butyl ester；(S)-(1-phenylethyl)carbamic acid tert-butyl ester；N-tert-butoxycarbonyl-(S)-methylbenzylamine；(S)-tert-butyl-(1-phenylethyl)carbamate；(S)-t-butyl N-(1-phenylethyl)carbamate；tert-butyl N-[(1S)-1-phenylethyl]carbamate
• CAS: 147169-48-0
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: WOIRCKJMSPMDAM-JTQLQIEISA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  324.9±21.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-BOC-1-苯乙胺 在 甲烷磺酸 、 5,5-dibromohydantoin 作用下， 生成 (S)-(-)- α-甲基苄胺
  参考文献：
  名称：

  一种光学纯4-(1-氨基)乙基苯甲酸酯及其盐的制备方法

  摘要：

  本发明涉及一种光学纯4‑(1‑氨基)乙基苯甲酸酯及其盐的制备方法。所述方法具有价廉、环境友好、光学纯度高、操作简便、易于工业化生产的特点。

  公开号：

  CN112552200A
• 作为产物：
  描述：

  N-Boc-(p-methoxyphenyl)benzylamine 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 鹰爪豆碱 作用下， 反应 10.0h， 生成 (S)-N-BOC-1-苯乙胺
  参考文献：
  名称：

  (−)-Sparteine-Mediated α-Lithiation of N-Boc-N-(p-methoxyphenyl)benzylamine:  Enantioselective Syntheses of (S) and (R) Mono- and Disubstituted N-Boc-benzylamines

  摘要：

  DOI：

  10.1021/ja9538804

文献信息

• 1,1,1,3,3,3-Hexafluoroisopropanol: A Recyclable Organocatalyst for<i>N</i>-Boc Protection of Amines
  作者：Akbar Heydari、Samad Khaksar、Mahmood Tajbakhsh

  DOI：10.1055/s-2008-1067272

  日期：2008.10

  A simple and efficient protocol for the chemoselective mono-N-Boc protection of various structurally diverse amines with di-tert-butyl dicarbonate using 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as solvent and catalyst is described. The catalyst can be readily separated from the reaction products and recovered for direct reuse. No competitive side reactions such as formation of isocyanate, urea, and N,N-di-Boc were observed. α-Amino alcohols afforded the N-Boc derivatives without oxazolidinone formation.

  描述了一种简单且高效的化学选择性单-N-Boc保护多种结构多样性胺类的方法，使用二叔丁基二碳酸酯和1,1,1,3,3,3-六氟异丙醇（HFIP）作为溶剂和催化剂。催化剂可以轻易地从反应产物中分离并回收，以便直接重复使用。未观察到异氰酸酯、脲和N,N-二-Boc等竞争性副反应。α-氨基醇类在未形成恶唑烷酮的情况下获得了N-Boc衍生物。
• Protic ionic liquid [TMG][Ac] as an efficient, homogeneous and recyclable catalyst for Boc protection of amines
  作者：Jafar Akbari、Akbar Heydari、Leila Ma’mani、Seyed Hassan Hosseini

  DOI：10.1016/j.crci.2009.10.003

  日期：2010.5

  Résumé An efficient and practical protocol for the chemoselective N-Boc protection of various structurally different aryl, aliphatic and heterocyclic amines was carried out with (Boc)2O using protic 1, 1, 3, 3-tetra-methylguanidinium acetate (10 mol%) as recyclable catalyst under solvent free condition at ambient temperature. No competitive side reactions (isocyanate, urea and N, N-di-Boc) were observed. α-Amino alcohols afforded the N-Boc-derivative without oxazolidinone formation.

  简历 一种高效且实用的化学选择性N-Boc保护各种结构不同的芳基、脂肪族和杂环胺的协议，通过在无溶剂条件下使用质子化的1,1,3,3-四甲基胍乙酸盐（10 mol%）作为可回收催化剂，在室温下使用(Boc)2O进行。未观察到竞争性的副反应（异氰酸酯、脲和N,N-二Boc）。α-氨基醇提供了N-Boc衍生物而不形成噁唑烷酮。
• Direct Stereospecific Amination of Alkyl and Aryl Pinacol Boronates
  作者：Scott N. Mlynarski、Alexander S. Karns、James P. Morken

  DOI：10.1021/ja305448w

  日期：2012.10.10

  The direct amination of alkyl and aryl pinacol boronates is accomplished with lithiated methoxyamine. This reaction directly provides aliphatic and aromatic amines, stereospecifically, and without preactivation of the boronate substrate.

  烷基和芳基频哪醇硼酸酯的直接胺化是用锂化甲氧基胺完成的。该反应直接提供脂肪族和芳香族胺，立体定向，并且没有硼酸酯底物的预活化。
• ZnO Nanorods as an Efficient and Heterogeneous Catalyst for N-Boc Protection of Amines and Amine Derivatives
  作者：Azita Nouri、Jafar Akbari、Akbar Heydari、Arezu Nouri

  DOI：10.2174/157017811794557859

  日期：2011.1.1

  An efficient ZnO nano catalyst, which was readily prepared from Zn(CH3CO2)2, 2H2O and PVP by a chemical solution approach has successfully catalyzed N-tertbutoxy carbonylation of amines. The ZnO nanorods were successful and gave promising results for highly active and chemoselective as well as easily recyclable catalyst for the NBoc protection reaction of a wide variety of amines. The catalyst could be easily recycled for five times without noticeable decrease in catalytic activity. The ZnO nanocatalyst was characterized with XRD and SEM.

  一种高效的ZnO纳米催化剂，通过化学溶液法制备，原料为Zn(CH3CO2)2·2H2O和PVP，成功催化了胺的N-叔丁氧羰基化反应。ZnO纳米棒作为催化剂表现出色，为各种胺的NBoc保护反应提供了高活性、化学选择性且易于回收的催化剂，并显示出良好的结果。该催化剂可轻松回收利用五次，催化活性未见明显下降。通过XRD和SEM对ZnO纳米催化剂进行了表征。
• N-tert-Butoxycarbonylation of amines using H3PW12O40 as an efficient heterogeneous and recyclable catalyst
  作者：Akbar Heydari、Roohollah Kazem Shiroodi、Hossein Hamadi、Maryam Esfandyari、Mehrdad Pourayoubi

  DOI：10.1016/j.tetlet.2007.06.064

  日期：2007.8

  heteropoly acid H3PW12O40 (0.5 mol %) is a very efficient and environmentally benign catalyst for N-tert-butoxycarbonylation of amines (primary, secondary) with di-tert-butyl dicarbonate at room temperature in short reaction times (<10 min). No competitive side products such as isocyanates, ureas, N,N-di-tert-butoxycarbonyls, O-Boc and oxazolidinones were observed. Chiral α-amino alcohols and esters

  市售的杂多酸H 3 PW 12 O 40（0.5 mol％）是一种非常有效且对环境无害的催化剂，用于在室温下短时间反应中用二碳酸二叔丁酯将胺（伯，仲）的N-叔丁氧羰基化次（<10分钟）。没有竞争的副产物如异氰酸酯，脲，Ñ，ñ -二-叔-butoxycarbonyls，ö -Boc和恶唑烷酮观察。手性α-氨基醇和酯以优异的产率化学选择性地提供了相应的N- Boc衍生物。