tert-butyl (4-isocyanobutyl)carbamate | 353505-05-2

• 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 (4-isocyanobutyl)carbamate
• 英文别名: tert-butyl N-(4-isocyanobutyl)carbamate
• CAS: 353505-05-2
• 化学式: C₁₀H₁₈N₂O₂
• mdl: MFCD11223684
• 分子量: 198.265
• InChiKey: IQLSCBFFDOONPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-isocyanobutyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.02h， 生成 (2S)-methyl 1-(2-((4-aminobutyl)amino)-2-oxo-1-phenylethyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  使用α-异氰基-ω-羧酸的多功能多组分反应大环合成

  摘要：

  介绍了通过Ugi多组分反应直接合成大环α-异氰基-ω-羧酸的方法。这种多组分反应（MCR）协议的不同之处在于，它特别短，会聚且通用，可访问12-22个成员环。

  DOI：

  10.1021/acs.orglett.5b02419
• 作为产物：
  描述：

  4-(tert-butoxycarbonylamino)butylformamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以43%的产率得到tert-butyl (4-isocyanobutyl)carbamate
  参考文献：
  名称：

  精巧地合成受精蛋白诱导的具有广谱抗生素活性的分子†

  摘要：

  越来越需要鉴定新的广谱抗生素。先前已证明天然产物pergualin具有令人鼓舞的抗菌活性和特权结构，但其具有挑战性的合成方法限制了其进一步的开发。例如，已经报道了大约10个线性步骤中精子精及其类似物的合成，总收率在0.3％至18％之间。使用Ugi多组分反应，我们只需一步即可组装受精子激发的分子，从而显着提高了总收率（20％至96％）。使用这种策略，我们生成了43种新的类似物，并测试了它们对两种革兰氏阴性和四种革兰氏阳性菌株的抗菌活性。我们发现最有效的类似物化合物6的MIC值为4至32μgmL -1对抗这六种菌株，这对精子蛋白（MIC〜6.25至50μgmL -1）有显着改善。这些研究为使用新型化学支架制备广谱抗生素提供了一条简洁的途径。

  DOI：

  10.1039/c4md00572d

文献信息

• Automated, Accelerated Nanoscale Synthesis of Iminopyrrolidines
  作者：Angelina Osipyan、Shabnam Shaabani、Robert Warmerdam、Svitlana V. Shishkina、Harry Boltz、Alexander Dömling

  DOI：10.1002/anie.202000887

  日期：2020.7.20

  agrochemical, and materials research and development. Herein, we describe the synthesis of iminopyrrolidine‐2‐carboxylic acid derivatives using chiral glutamine, oxo components, and isocyanide building blocks in an unprecedented Ugi‐3‐component reaction. We used I‐DOT, a positive‐pressure‐based low‐volume and non‐contact dispensing technology to prepare more than 1000 different derivatives in a fully automated

  合成化学的小型化和加速是制药、农化和材料研究与开发的新兴领域。在此，我们描述了在前所未有的 Ugi-3 组分反应中使用手性谷氨酰胺、含氧组分和异氰化物结构单元合成亚氨基吡咯烷-2-羧酸衍生物。我们使用 I-DOT（一种基于正压的小容量非接触式点胶技术）以全自动方式制备了 1000 多种不同的衍生物。一般来说，该反应是立体选择性的，收率良好，并且能耐受多种官能团。我们举例说明了快速高效的纳摩尔级探索到毫摩尔级合成的流程，以发现大范围有用的新型反应。
• Improved synthesis of 15-deoxyspergualin analogs using the Ugi multi-component reaction
  作者：Christopher G. Evans、Matthew C. Smith、James P. Carolan、Jason E. Gestwicki

  DOI：10.1016/j.bmcl.2011.02.079

  日期：2011.5

  Spergualin is a natural product that exhibits immunosuppressive, anti-tumor and anti-bacterial activities. Its derivatives, such as 15-deoxyspergualin (15-DSG), have been clinically approved for acute allograft rejection. However, the reported syntheses are cumbersome (>10 steps) and they suffer from low overall yields (similar to 0.3% to 18%). Moreover, spergualin and its derivatives are chemically unstable and rapidly hydrolyzed in aqueous buffer. Here, we have re-explored these issues and report a modified synthetic route with significantly improved overall yield (similar to 31% to 47%). The key transformation is a microwave-accelerated Ugi multi-component reaction that is used to generate the peptoid core in a single step. Using the products of this route, we found that modifications of the hemiaminal significantly increased chemical stability. Thus, we anticipate that this synthetic route will improve access to biologically active 15-DSG derivatives. (C) 2011 Elsevier Ltd. All rights reserved.
• Identification of inhibitors of heparin–growth factor interactions from combinatorial libraries of four-component condensation reactions
  作者：Jundong Zhang、Georgiana Rivers、Yanyi Zhu、Alan Jacobson、James Peyers、Gretchen Grundstrom、Peter Burch、Sohail Hussein、Ariane Marolewski、Walter Herlihy、James Rusche

  DOI：10.1016/s0968-0896(00)00317-5

  日期：2001.4

  Chemical libraries based on four-component condensation (4CC) reactions of isocyanides were constructed to identify compounds capable of blocking heparin binding to vascular endothelial growth factor (VEGF) and basic fibroblast growth factor (bFGF). The reaction products in the synthesized libraries contain heparin mimetic functional groups such as carbohydrates, sulfonates, carboxylates, and hydroxy groups. These libraries have been screened for the inhibition of heparin binding to growth factors such as VEGF and bFGF. Single point screening at 5.0 muM of the 18,720 reaction products generated 26 candidates. The IC(50)s of these 26 compounds were determined using HPLC-purified products and 20 of the 26 showed significant inhibition of heparin binding to VEGF and/or bFGF. Eighteen of the 20 confirmed active compounds have a linear extended structure. Structures identified in this library revealed an initial relationship of structure and activity, thus providing direction for further investigation of this type of heparin mimetic libraries. (C) 2001 Published by Elsevier Science Ltd.