Z-Leu-ψ[CH2NHCHO] | 1245908-84-2

• 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: Z-Leu-ψ[CH2NHCHO]
• 英文别名: (S)-benzyl 1-formamido-4-methylpentan-2-ylcarbamate
• CAS: 1245908-84-2
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: VDTFETQQPJUDRG-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Z-Leu-ψ[CH2NHCHO] 在 伯吉斯试剂 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到Z-Leu-ψ[CH2NC]
  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：

  甲酸 、 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到Z-Leu-ψ[CH2NHCHO]
  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

文献信息

• A Simple Approach for the Synthesis of Thio-, Dithio- and Selenothiocarbamate-Tethered Peptidomimetics
  作者：Vommina Sureshbabu、H. Lalithamba、T. Vishwanatha、M. Reddy

  DOI：10.1055/s-0031-1290683

  日期：2012.6

  A simple and efficient method is described for the synthesis of thio-, dithio- and selenothiocarbamate-linked peptidomimetics. The nucleophilic addition of enantiopure N I±-protected amino alkyl thiols to isocyanates, isothiocyanates or isoselenocyanates obtained from amino acid esters proceeds smoothly in the presence of catalytic amount of DMAP. The protocol was further extended for the synthesis

  描述了一种简单有效的方法来合成硫代、二硫代和硒代硫代氨基甲酸酯连接的肽模拟物。在催化量的 DMAP 存在下，对映体纯 NI± 保护的氨基烷基硫醇与由氨基酸酯获得的异氰酸酯、异硫氰酸酯或异硒氰酸酯的亲核加成顺利进行。该协议进一步扩展用于合成 N，N-正交保护的硫代、二硫代和硒代硫代氨基甲酸酯连接的肽模拟物。反应温和，无外消旋化，产物收率良好。© Georg Thieme Verlag 斯图加特·纽约。