ethyl α-diazomethylacetate

• 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: ethyl α-diazomethylacetate
• 英文别名: ethyl 3-diazopropanoate；ethyl diazoacetate；β-Diazo-propionsaeure-aethylester
• 化学式: C₅H₈N₂O₂
• 分子量: 128.131
• InChiKey: YMHSTHHCSOSNAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-二硝基酚 、 ethyl α-diazomethylacetate 在 乙醚 、 苯 作用下， 生成 3-(2,4-dinitro-phenoxy)-propionic acid
  参考文献：
  名称：

  Esters of β-Diazopropionic Acid. A New Synthesis of β-Aryloxypropionic Acids^1,2

  摘要：

  DOI：

  10.1021/ja01535a027

文献信息

• Stereoselective Synthesis of 1,4,5-Tri-<i>cis</i>-guaiane Sesquiterpene: First Total Synthesis of (−)-Dendroside C Aglycon
  作者：Jaehoon Sim、Hyunkyung Park、Juhee Lim、Inah Yoon、Changjin Lim、Hongchan An、Hwayoung Yun、Hyun Jin Choi、Young-Ger Suh

  DOI：10.1021/acs.orglett.7b03701

  日期：2018.2.2

  The first total synthesis of (−)-dendroside C aglycon, consisting of a 1,4,5-tri-cis-guaiane skeleton, from a versatile hydroazulene intermediate has been accomplished. The key features of the syntheses include the stereoselective preparation of the unusual cis-hydroazulene core via a sequence of a unique Dieckmann condensation of the bicyclic lactone system, which was concisely prepared by the tandem

  已完成了从一种多功能的水az烯中间体首次合成由（1,4,5-三顺式-guaiane骨架）组成的（-）-树胶苷C糖苷配基。合成的关键特征包括通过双环内酯系统独特的Dieckmann缩合的序列立体选择性地制备不寻常的顺式-氢氮杂烯核，该序列是通过串联共轭加成和丁烯内酯前体的分子内烯丙基烷基化而简明地制备的，以及卡宾介导的环丙烷化反应制备具有特征性的三环骨架。
• Highly Diastereoselective and Enantioselective Olefin Cyclopropanation Using Engineered Myoglobin-Based Catalysts
  作者：Melanie Bordeaux、Vikas Tyagi、Rudi Fasan

  DOI：10.1002/anie.201409928

  日期：2015.2.2

  Using rational design, an engineered myoglobin‐based catalyst capable of catalyzing the cyclopropanation of aryl‐substituted olefins with catalytic proficiency (up to 46 800 turnovers) and excellent diastereo‐ and enantioselectivity (98–99.9 %) was developed. This transformation could be carried out in the presence of up to 20 g L−1 olefin substrate with no loss in diastereo‐ and/or enantioselectivity

  通过合理的设计，开发了一种工程化的基于肌红蛋白的催化剂，该催化剂能够催化芳基取代的烯烃的环丙烷化，具有催化能力（高达46 800次营业额）和出色的非对映和对映选择性（98–99.9％）。该转化可在不超过20 g L -1烯烃底物的存在下进行，且非对映选择性和/或对映选择性不损失。诱变和机理研究支持由亲电的血红素结合的卡宾物质介导的环丙烷化机理，并提供了一个模型来合理化蛋白质催化剂的立体偏好。这项工作表明，肌红蛋白是开发具有卡宾转移反应性的生物催化剂的有前途和强大的支架。
• Borane promoted aryl transfer reaction for the synthesis of α-aryl functionalised β-hydroxy and β-keto esters
  作者：Tanja Kaehler、Jonas Lorenz、Darren M. C. Ould、Dorothea Engl、Micol Santi、Lukas Gierlichs、Thomas Wirth、Rebecca L. Melen

  DOI：10.1039/d2ob00643j

  日期：——

  The synthesis of a series of α-aryl or α-alkyl functionalised β-hydroxy and β-keto esters has been achieved by reacting α-diazoesters with boranes, and aldehydes, ketones, anhydrides, nitriles, esters or isocyanates. In a mild reaction protocol, 26 examples are presented in yields up to 73%.

  通过使 α-重氮酯与硼烷、醛、酮、酸酐、腈、酯或异氰酸酯反应，可以合成一系列 α-芳基或 α-烷基官能化的 β-羟基和 β-酮酯。在温和的反应方案中，26 个示例的产率高达 73%。
• Novel N′-benzylidene benzofuran-3-carbohydrazide derivatives as antitubercular and antifungal agents
  作者：Vikas N. Telvekar、Anirudh Belubbi、Vinod Kumar Bairwa、Kalpana Satardekar

  DOI：10.1016/j.bmcl.2012.01.067

  日期：2012.3

  Tuberculosis constitutes today a serious threat to human health worldwide, aggravated by the increasing number of identified multi-drug resistant strains of Mycobacterium tuberculosis (Mtb), its causative agent, as well as by the lack of development of novel mycobactericidal compounds for the last few decades. A novel series of benzofuran-3-carbohydrazide and its analogs was synthesized and characterized spectroscopically. All the compounds were characterized and screened for in vitro anti-tuberculosis (anti-TB) activity against Mycobacterium tuberculosis H37Rv strains by using resazurin assay utilizing microtiter-plate method (REMA). These compounds also showed good antifungal activity against Candida albicans. Thus, the high level of activity shown by the compounds (8a, 8k) suggests that these compounds could serve as leads for development of novel synthetic compounds with enhanced anti- TB and antifungal activity. (C) 2012 Elsevier Ltd. All rights reserved.
• LOOKER J. H.; BRANNIGAN L. H.; PROKOP R. J., J. HETEROCYCL. CHEM. <JHTC-AD>, 1975, 12, NO 3, 537-540
  作者：LOOKER J. H.、 BRANNIGAN L. H.、 PROKOP R. J.

  DOI：——

  日期：——