tert-butyl 4-phenylbutylcarbamate | 285119-71-3

• 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: tert-butyl 4-phenylbutylcarbamate
• 英文别名: tert-Butyl (4-phenylbutyl)carbamate；tert-butyl N-(4-phenylbutyl)carbamate
• CAS: 285119-71-3
• 化学式: C₁₅H₂₃NO₂
• mdl: MFCD24393186
• 分子量: 249.353
• InChiKey: BTVSVROCBMADMI-UHFFFAOYSA-N

物化性质

• 沸点：
  375.8±21.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl ((5-phenylpentanoyl)oxy)carbamate 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以86%的产率得到tert-butyl 4-phenylbutylcarbamate
  参考文献：
  名称：

  Base-Mediated Intramolecular Decarboxylative Synthesis of Alkylamines from Alkanoyloxycarbamates

  摘要：

  A general and effective method for the synthesis of alkylamine via intramolecular decarboxylation of alkanoyloxycarbamates is described. The alkanoyloxycarbamates are readily prepared with alkyl carboxylic acids and hydroxylamine. The reaction shows a broad range of substrates (primary and secondary alkyl) with functional tolerance, and the corresponding products were obtained in good yields under mild conditions.

  DOI：

  10.1021/acs.joc.8b00970

文献信息

• A generic approach for the catalytic reduction of nitriles
  作者：Stephen Caddick、Duncan B Judd、Alexandra K.de K Lewis、Melanie T Reich、Meredith R.V Williams

  DOI：10.1016/s0040-4020(03)00858-5

  日期：2003.7

  The scope of nickel boride mediated reduction of nitriles has been extended further to allow the preparation of Boc protected amines via a mild catalytic process. It is noteworthy that the toxicity of this procedure is greatly reduced due to its catalytic nature in nickel(II) chloride used in combination with excess sodium borohydride. The protocol is marked by its resilience towards air and moisture

  硼化镍介导的腈还原的范围进一步扩大，以允许通过温和的催化过程制备Boc保护的胺。值得注意的是，由于该方法在与过量的硼氢化钠组合使用的氯化镍（II）中的催化性质，因此大大降低了该方法的毒性。该协议以其对空气和湿气的适应性而著称，因此是一种简单而通用的实用协议。
• Convenient synthesis of protected primary amines from nitriles
  作者：Stephen Caddick、Alexandra K de K. Haynes、Duncan B Judd、Meredith R.V Williams

  DOI：10.1016/s0040-4039(00)00410-x

  日期：2000.4

  Investigations into the use of nickel chloride and sodium borohydride for the reduction of nitriles showed the secondary amine dimers to be the major products under normal conditions. The addition of a suitable trapping agent, such as di-tert-butyl dicarbonate, allowed the isolation of the protected primary amines.

  关于使用氯化镍和硼氢化钠还原腈的研究表明，仲胺二聚体是正常条件下的主要产物。加入合适的捕集剂，如二-叔丁基二碳酸酯，允许的受保护的伯胺的隔离。
• Synthesis of 1‐Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions
  作者：Yuya Miki、Naohito Tomita、Kazuho Ban、Hironao Sajiki、Yoshinari Sawama

  DOI：10.1002/adsc.202100329

  日期：2021.7.20

  We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner.

  我们在此报告了在热和中性条件下从环丁基叠氮化物有效和系统地合成 1-吡咯啉。反应在没有任何额外试剂的情况下进行，生成的唯一副产物是氮气。此外，生成的 1-吡咯啉可以以一锅法连续转化为吡咯、N -Boc-胺和氧氮丙啶。
• Application of [Co(Corrole)] ^– Complexes in Ring‐Closing C–H Amination of Aliphatic Azides via Nitrene Radical Intermediates
  作者：Monalisa Goswami、Paul Geuijen、Joost. N. H. Reek、Bas de Bruin

  DOI：10.1002/ejic.201701343

  日期：2018.2.7

  DFT calculations, the reaction is proposed to proceed via discrete open‐shell nitrene radical intermediates bearing most of their spin density at the nitrene nitrogen atom. The [CoII(Cor)]– complexes are substantially faster catalysts than the corresponding neutral [CoII(porphyrin)] complexes when applied in the same ring‐closing C–H amination reaction under identical reaction conditions. Increasing

  在 Boc2O（Boc = 叔丁氧羰基）存在下，阴离子 [CoII(Cor)]– (Cor = corrole) 金属基团在脂肪族叠氮化物的闭环 C–H 胺化中的合成、表征和应用，得到相应的报道了 Boc 保护的 N-杂环产物叔丁基 2-苯基吡咯烷-1-羧酸酯。这是在氮烯转移反应中使用金属基钴 (II) 钴络合物的第一个例子。在 DFT 计算的基础上，该反应被提议通过离散的开壳氮烯自由基中间体进行，这些中间体在氮烯氮原子处具有大部分自旋密度。[CoII(Cor)]– 配合物在相同的反应条件下用于相同的闭环 C-H 胺化反应时，是比相应的中性 [CoII(卟啉)] 配合物更快的催化剂。
• Boc-Protected Amines via a Mild and Efficient One-Pot Curtius Rearrangement
  作者：Hélène Lebel、Olivier Leogane

  DOI：10.1021/ol051428b

  日期：2005.9.1

  [reaction: see text] The reaction of a carboxylic acid with di-tert-butyl dicarbonate and sodium azide allowed the formation of an acyl azide intermediate, which undergoes a Curtius rearrangement in the presence of tetrabutylammonium bromide and zinc(II) triflate. The trapping of the isocyanate derivative in the reaction mixture led to the desired tert-butyl carbamate in high yields at low temperature

  [反应：见正文]羧酸与二碳酸二叔丁酯和叠氮化钠的反应允许形成酰基叠氮化物中间体，该中间体在溴化四丁铵和三氟甲磺酸锌（II）的存在下进行库尔修斯重排。异氰酸酯衍生物在反应混合物中的捕集在低温下以高收率得到所需的氨基甲酸叔丁酯。这些反应条件与多种底物兼容，包括丙二酸酯衍生物，这些底物可提供被保护氨基酸的通道。