(S)-tert-butyl (1-cyano-2-phenylethyl)carbamate | 930101-83-0

• 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: (S)-tert-butyl (1-cyano-2-phenylethyl)carbamate
• 英文别名: tert-butyl N-[(2S)-1-amino-1-hydroxyimino-3-phenylpropan-2-yl]carbamate
• CAS: 930101-83-0
• 化学式: C₁₄H₂₁N₃O₃
• 分子量: 279.339
• InChiKey: WUFWXDOQAQMJPT-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl (1-cyano-2-phenylethyl)carbamate 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 93.0h， 生成 (S)-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-phenylethanamine, TFA
  参考文献：
  名称：

  [EN] IAP ANTAGONISTS
  [FR] ANTAGONISTES D'IAP

  摘要：

  已披露调节凋亡抑制剂（IAPs）活性的化合物，包含该化合物的药物组合物以及利用本发明的化合物治疗增殖性疾病和失调凋亡疾病（如癌症）的方法。

  公开号：

  WO2013192286A1
• 作为产物：
  描述：

  (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 在 吡啶 、 盐酸羟胺 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 (S)-tert-butyl (1-cyano-2-phenylethyl)carbamate
  参考文献：
  名称：

  含恶二唑杂合体文库的设计、合成和细胞毒性评估。

  摘要：

  混合化合物的开发导致发现了一些最严重的疾病（包括癌症）的新药理活性剂。在此，我们描述了通过分子杂交方法设计的一系列新的含恶二唑结构。青霉素衍生物和氨基酸通过形成 1,2,4-恶二唑环与氨基酸和芳香部分相连。或者，氨基酸衍生的酰肼和活化的青霉酸之间的缩合导致一系列含 1,3,4-恶二唑青霉素的杂化物和非环化的二酰肼。从细胞毒性分析中可以看出，连接青霉素和脂肪族氨基酸的两种 1,2,4-恶二唑和一种 1,3,4-恶二唑表现出高度的细胞毒性选择性，对肿瘤细胞的效力是正常细胞的三到四倍。结果给出了一个非常有趣的观点，表明这些杂合化合物可以提供一种具有良好细胞毒性特征的新型抗肿瘤支架。

  DOI：

  10.1039/d1ra05602f

文献信息

• The preparation of optically active α-amino 4H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids
  作者：John E. Mangette、Matthew R. Johnson、Van-Duc Le、Rajesh A. Shenoy、Howard Roark、Michael Stier、Thomas Belliotti、Thomas Capiris、Peter R. Guzzo

  DOI：10.1016/j.tet.2009.09.045

  日期：2009.11

  Optically active α-amino 4H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described.

  在五个合成步骤中，由旋光性α-氨基酸制备旋光性α-氨基4 H- [1,2,4]恶二唑-5-酮（恶二唑酮）。恶二唑酮部分用作羧酸的生物立体替代物。描述了将α-氨基恶二唑酮掺入代表性的二肽模拟物中。
• Structure-based design of novel dihydroisoquinoline BACE-1 inhibitors that do not engage the catalytic aspartates
  作者：Simeon Bowers、Ying-zi Xu、Shendong Yuan、Gary D. Probst、Roy K. Hom、Wayman Chan、Andrei W. Konradi、Hing L. Sham、Yong L. Zhu、Paul Beroza、Hu Pan、Eric Brecht、Nanhua Yao、Julie Lougheed、Danny Tam、Zhao Ren、Lany Ruslim、Michael P. Bova、Dean R. Artis

  DOI：10.1016/j.bmcl.2013.01.103

  日期：2013.4

  The structure-activity relationship of a series of dihydroisoquinoline BACE-1 inhibitors is described. Application of structure-based design to screening hit 1 yielded sub-micromolar inhibitors. Replacement of the carboxylic acid of 1 was guided by X-ray crystallography, which allowed the replacement of a key water-mediated hydrogen bond. This work culminated in compounds such as 31, which possess good BACE-1 potency, excellent permeability and a low P-gp efflux ratio. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles as peptidomimetic building blocks
  作者：Žiga Jakopin、Robert Roškar、Marija Sollner Dolenc

  DOI：10.1016/j.tetlet.2006.12.077

  日期：2007.2

  Twelve new 1,2,4-oxadiazole based compounds have been synthesized. Their structures contain a protected amine and a carboxyl or an ester group, and thus serve as potential peptidomimetic building blocks. The synthetic route is simple and mild conditions are used so that the chirality of the starting amino acids is retained. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics
  作者：Vommina V. Sureshbabu、Hosahalli P. Hemantha、Shankar A. Naik

  DOI：10.1016/j.tetlet.2008.06.091

  日期：2008.8

  The synthesis of a new class of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics is described. The protocol employs a reaction between an N-protected amino acyl fluoride and an amino acid-derived amidoxime. All the three commonly employed urethanes have been used in this protocol for N-protection. The course of the reaction was found to be high yielding and all new compounds were well characterized by NMR and mass spectroscopy. The C-acyl amidoxime intermediate has also been isolated as a stable solid. (C) 2008 Elsevier Ltd. All rights reserved.