methyl (E)-4-((tert-butoxycarbonyl)amino)but-2-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E)-4-((tert-butoxycarbonyl)amino)but-2-enoate
• 英文别名: Tert-butyl (e)-3-(methoxycarbonyl)allylcarbamate；methyl (E)-4-[(2-methylpropan-2-yl)oxycarbonylamino]but-2-enoate
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: MSDZHXDAPLPIIO-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-((tert-butoxycarbonyl)amino)but-2-enoate 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以85.6%的产率得到(E)-4-aminobut-2-enoic acid hydrochloride
  参考文献：
  名称：

  Efficient synthesis of the GABAA receptor agonist trans-4-aminocrotonic acid (TACA)

  摘要：

  Investigations into the pharmacology of different types of cys-loop GABA receptor have relied for years on the chemical modification of GABA-like compounds. The GABA metabolite GABOB is an attractive molecule to modify due to its convenient chemical structure. In the process of developing new GABA-mimic compounds from GABOB as a starting compound three small molecule GABA derivatives were synthesized using a variety of chemical transformations. Amongst these, a new and reliable method to synthesize TACA (trans-4-aminocrotonic acid) is reported. Crown Copyright (C) 2017 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.07.050
• 作为产物：
  描述：

  methyl 2-<(R)-2-oxo-5-oxazolidinyl>acetate 在 4-二甲氨基吡啶 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 methyl (E)-4-((tert-butoxycarbonyl)amino)but-2-enoate
  参考文献：
  名称：

  Enantioselective Enzymatic Aminolysis and Ammonolysis of Dimethyl 3-Hydroxyglutarate. Synthesis of (R)-4-Amino-3-hydroxybutanoic Acid

  摘要：

  DOI：

  10.1021/jo960468d

文献信息

• [EN] HETEROARYL INHIBITORS OF PAD4<br/>[FR] INHIBITEURS HÉTÉROARYLES DE PAD4
  申请人：PADLOCK THERAPEUTICS INC

  公开号：WO2018049296A1

  公开（公告）日：2018-03-15

  The present invention provides compounds useful as inhibitors of PAD4, compositions thereof, and methods of treating PAD4-related disorders.

  本发明提供了作为PAD4抑制剂有用的化合物，其组合物以及治疗与PAD4相关疾病的方法。
• A DNA‐Encoded Chemical Library Incorporating Elements of Natural Macrocycles
  作者：Cedric J. Stress、Basilius Sauter、Lukas A. Schneider、Timothy Sharpe、Dennis Gillingham

  DOI：10.1002/anie.201902513

  日期：2019.7.8

  Here we show a seven‐step chemical synthesis of a DNA‐encoded macrocycle library (DEML) on DNA. Inspired by polyketide and mixed peptide‐polyketide natural products, the library was designed to incorporate rich backbone diversity. Achieving this diversity, however, comes at the cost of the custom synthesis of bifunctional building block libraries. This study outlines the importance of careful retrosynthetic

  在这里，我们展示了在DNA上进行DNA编码的大环文库（DEML）的七步化学合成。受聚酮化合物和肽-聚酮化合物混合天然产物的启发，该文库旨在整合丰富的骨架多样性。但是，要实现这种多样性，就要以双功能构件块库的定制合成为代价。这项研究概述了在DNA编码文库中仔细进行逆向合成设计的重要性，同时揭示了需要新的DNA合成方法的领域。
• Carboxyl-modified amino acids and peptides as protease inhibitors
  作者：Stewart A. Thompson、Peter R. Andrews、Robert P. Hanzlik

  DOI：10.1021/jm00151a018

  日期：1986.1

  mM, and k2 = 0.015 and 0.010 s-1, respectively). Inhibition of DPP-I by 3d provides only the second example of a cysteine protease which is strongly inhibited by a nitrile analogue of a specific substrate. Further studies are needed to determine the generality and potential utility of this finding. Compounds 3e, 3f, and 4e exemplify a new class of specific affinity labels for cysteine proteases whose

  制备几种类型的羧基修饰的氨基酸和肽，它们具有适合于几种代表性蛋白酶之一的N末端修饰（载体片段），并评估了它们对这些酶的抑制作用。羧基修饰（抑制单元）包括（b）CONH 2，（c）CSNH 2，（d）CN，（e）反式-CH ＝ CHCO 2 Me和（f）反式-CH ＝ CHSO 2 Me。载体片段包括NH2（PhCH2）CHX（1），AcNH（PhCH2）CHX（2），H2NCH2CONH（PhCH2）CHX（3）和AcNH（PhCH2）CHCONHCH2X（4）。化合物1b，1d，1e和1f是微粒体和胞质亮氨酸氨基肽酶的竞争性抑制剂（前者的Ki分别为14.8、67、61和3.7 mM，后者分别为14.1、26.4、27.3和8.8 mM） 。化合物1c和亮氨酸硫代酰胺均对这两种酶均无任何可检测的作用。化合物2b-f还是胰凝乳蛋白酶的竞争性抑制剂（Ki分别为13.9、23.0、5.3、30.8和29
• Dramatic Effect of Boron-Based Lewis Acids in Cross-Metathesis Reactions
  作者：Laurent Elkaïm、Laurence Grimaud、Emeline Vedrenne、Hervé Dupont、Sabrina Oualef

  DOI：10.1055/s-2005-862375

  日期：——

  Amino compounds such as allylic carbamates or amides are poor partners in cross-metathesis reactions because of possible coordination of the emerging carbene to the polar functional group. Whereas the use of titanium Lewis acid catalysts was unsatisfactory, an impressive increase in yields was obtained with boron-based Lewis acids.

  氨基化合物如烯丙基氨基甲酸酯或酰胺在交叉烯烃重排反应中表现不佳，因为新形成的卡宾可能与极性官能团发生配位。虽然使用钛路易斯酸催化剂的效果不尽如人意，但使用硼基路易斯酸则显著提高了产率。
• Enantioselective vicinal hydroxylation of terminal and E-1,2-disubstituted olefins by a chiral complex of osmium tetroxide. An effective controller system and a rational mechanistic model
  作者：E. J. Corey、Paul DaSilva Jardine、Scott Virgil、Po Wai Yuen、Richard D. Connell

  DOI：10.1021/ja00208a025

  日期：1989.12

  The suprafacial hydroxylation of olefins by osmium tetraoxide, though a much used synthetic method, would become even more important if three conditions could be met: (1) modification to achieve high and predictable enantioselectivity and acyclic diastereoselectivity, (2) clarification of reaction mechanism, and (3) facilitated recovery and recycling of osmium. This paper reports progress on all three

  四氧化锇表面羟基化烯烃虽然是一种常用的合成方法，但如果满足三个条件，则将变得更加重要：（1）改性以实现高且可预测的对映选择性和非环非对映选择性，（2）阐明反应机理， (3)促进锇的回收和再循环。本文报告了所有三个方面的进展。