tert-butyl ((1S,2S)-1-cyano-2-methylbutyl)carbamate | 1120367-07-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl ((1S,2S)-1-cyano-2-methylbutyl)carbamate
• 英文别名: N-tert-butyloxycarbonyl isoleucine nitrile；tert-butyl N-[(1S,2S)-1-cyano-2-methylbutyl]carbamate
• CAS: 1120367-07-8
• 化学式: C₁₁H₂₀N₂O₂
• 分子量: 212.292
• InChiKey: FZTVKXQXWQJUTR-DTWKUNHWSA-N

物化性质

• 沸点：
  318.9±25.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl ((1S,2S)-1-cyano-2-methylbutyl)carbamate 在 lithium aluminium tetrahydride 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 carbamic acid, <1-(aminomethyl)-2-methylbutyl>-, 1,1-dimethylethyl ester,
  参考文献：
  名称：

  Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

  摘要：

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.082
• 作为产物：
  描述：

  Boc-L-异亮氨酰胺 在 吡啶 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到tert-butyl ((1S,2S)-1-cyano-2-methylbutyl)carbamate
  参考文献：
  名称：

  α-氨基酸衍生的 Boc-氨基四唑的合成

  摘要：

  摘要 描述了从 N α-Boc 氨基酸开始合成 Boc 保护的四唑氨基酸类似物的简单途径。在催化量的溴化锌存在下，Boc-α-氨基腈和叠氮化钠的[2+3]环加成以良好的产率和纯度得到所需的四唑。获得的所有化合物均已通过 1H 和 13C-NMR 和质谱研究进行表征。

  DOI：

  10.1080/00397910802374133

文献信息

• Synthesis of Boc-Amino Tetrazoles Derived from α-Amino Acids
  作者：Vommina V. Sureshbabu、Shankar A. Naik、G. Nagendra

  DOI：10.1080/00397910802374133

  日期：2009.1.13

  Abstract A simple route for the synthesis of Boc-protected tetrazole analogs of amino acids starting from N α-Boc amino acids has been described. The [2 + 3] cycloaddition of Boc-α-amino nitrile and sodium azide in the presence of a catalytic amount of zinc bromide yielded the desired tetrazoles in good yields and purity. All the compounds obtained have been characterized by 1H and 13C-NMR and mass

  摘要 描述了从 N α-Boc 氨基酸开始合成 Boc 保护的四唑氨基酸类似物的简单途径。在催化量的溴化锌存在下，Boc-α-氨基腈和叠氮化钠的[2+3]环加成以良好的产率和纯度得到所需的四唑。获得的所有化合物均已通过 1H 和 13C-NMR 和质谱研究进行表征。
• Total Synthesis of the Cyclic Dodecapeptides Wewakazole and Wewakazole B
  作者：Martyn Inman、Hannah L. Dexter、Christopher J. Moody

  DOI：10.1021/acs.orglett.7b01393

  日期：2017.7.7

  tetrapeptide units, followed by peptide coupling and macrocyclization. The three oxazole amino acid fragments are readily accessible by rhodium(II)-catalyzed amide N–H insertion of diazocarbonyl compounds, or by the cycloaddition of rhodium carbenoids with nitriles.

  环状十二肽wewakazole和wewakazole B通过不同的策略，通过常见的含有tris-脯氨酸的恶唑八肽和两个单独的bis-恶唑的四肽单元合成，然后进行肽偶联和大环化。这三个恶唑氨基酸片段可通过重氮羰基化合物的铑（II）催化的酰胺N–H插入，或铑类化合物与腈的环加成而容易地获得。
• Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics
  作者：Gundala Chennakrishnareddy、Govindappa Nagendra、Hosahalli P. Hemantha、Ushati Das、Tayur N. Guru Row、Vommina V. Sureshbabu

  DOI：10.1016/j.tet.2010.06.082

  日期：2010.8

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.