2-(噻吩-2-基)乙基异丁酯 | 602268-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 2-(噻吩-2-基)乙基异丁酯
• 英文名称: 2-(thiophen-2-yl)ethyl isocyanide
• 英文别名: 2-(2-isocyanoethyl)thiophene；2-(2-thienyl)ethylisocyanide；2-(2-thienyl)ethyl isocyanide
• CAS: 602268-91-7
• 化学式: C₇H₇NS
• mdl: MFCD05222951
• 分子量: 137.205
• InChiKey: LZSOGQNQXJHKMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  32.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(噻吩-2-基)乙基异丁酯 、 环己甲酸 在 甲烷磺酸 、 magnesium sulfate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 2-cyclohexylcarbonyl-1,2,3,6,7,10b-hexahydrothieno<3',2':3,4>pyrido<1,2-a>pyrazin-4-one
  参考文献：
  名称：

  吡喹酮衍生物的 MCR 合成

  摘要：

  血吸虫病是一种影响全球 2 亿多人的大量被忽视的热带疾病，只能通过四氢异喹啉药物吡喹酮 (PZQ) 进行有效治疗。在此，我们描述了一种通过 Ugi 4 组分反应和 Pictet-Spengler 反应在两步单锅程序中获得 PZQ 衍生物的有效方法。基于 Ugi 4 组分反应描述了 30 种新型 PZQ 衍生物，并讨论了一种新型衍生物的 X 射线结构，与 PZQ 相比，揭示了不同的构象。基于体外曼氏血吸虫蠕虫活力测定，已经确定了几种在活性上与药物 PZQ 相当的类似物。

  DOI：

  10.1111/j.1747-0285.2011.01288.x
• 作为产物：
  描述：

  噻吩乙胺 在 三光气 、 碳酸氢钠 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 2-(噻吩-2-基)乙基异丁酯
  参考文献：
  名称：

  Small molecules enhance functional O-mannosylation of Alpha-dystroglycan

  摘要：

  Alpha-dystroglycan (alpha-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of alpha-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of alpha-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of alpha-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of alpha-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of alpha-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of alpha-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.011

文献信息

• Isocyanide 2.0
  作者：Pravin Patil、Maryam Ahmadian-Moghaddam、Alexander Dömling

  DOI：10.1039/d0gc02722g

  日期：——

  advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example

  异氰酸酯官能团由于其在类胡萝卜素和三键特征之间的二分法而具有亲核和亲电子末端碳，在有机化学中表现出不同寻常的反应性，例如在Ugi反应中。不幸的是，仅按比例使用几种异氰酸酯妨碍了有关该官能团引人入胜的反应性的新发现。具有多个官能团的多种异氰酸酯的合成漫长，效率低下，并使化学家暴露于危险的烟雾中。在这里，我们提出了一种创新的异氰酸酯合成方法，它通过避免在96孔微量滴定板中以0.2 mmol规模在0.5 mol克规模进行平行合成而避免的水后处理，克服了这些问题。我们方法的优势包括提高合成速度，在非常温和的条件下可以使用迄今为止从未有过的未知或高度反应性的异氰酸酯类，可以快速使用大量官能化的异氰酸酯，具有较高的收率，高纯度，经过验证的5个数量级以上的可扩展性，增加的安全性和较少的反应浪费，从而大大减少了环境脚印。例如，迄今为止认为是不稳定的2-异氰基嘧啶，2-酰基苯基异氰酸酯，甚至邻-异氰基苯甲醛
• Regioselective, Solvent-Free Synthesis of 3-Aminoimidazo[1,2-<i>a</i>]pyrimidines Under Microwave Irradiation Promoted by Zeolite HY
  作者：Beining Chen、Mark Thompson、Jenny Hurst

  DOI：10.1055/s-0028-1087274

  日期：——

  Microwave-assisted, solvent-free condensation of 2-aminopyrimidine with aldehydes and isonitriles gave the desired 3-aminoimidazo[1,2-a]pyrimidine products with good to excellent regioselectivity. A hydrogen zeolite (‘zeolite HY’) was found to be a novel and effective promoter for the reaction, generally leading to clean conversion and also permitting use of the normally unreactive 4,6-dimethyl-2-aminopyrimidine.

  微波辅助无溶剂的2-氨基嘧啶与醛和异腈的缩合反应产生了所需的3-氨基咪唑[1,2-a]嘧啶产物，具有良好到优异的区域选择性。研究发现氢分子筛（‘分子筛HY’）是该反应的一种新颖且有效的促进剂，通常能实现干净的转化，并且允许使用通常不反应的4,6-二甲基-2-氨基嘧啶。
• Novel Inhibitors of Glutaminyl Cyclase
  申请人：Thormann Michael

  公开号：US20080221086A1

  公开（公告）日：2008-09-11

  The present invention relates to compounds of formula (I), combinations and uses thereof for disease therapy, or a pharmaceutically acceptable salt, solvate or polymorph thereof, including all tautomers and stereoisomers thereof wherein R 1 represents heteroaryl; -carbocyclyl-heteroaryl; -alkenylheteroaryl or -alkylheteroaryl; R 2 represents alkyl which may optionally be substituted by hydroxy; carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl and hydroxy; aryl; -aryl-heteroaryl; -heteroaryl-aryl; -aryl-heterocyclyl; H; heteroaryl; or heterocyclyl, which may optionally be substituted by one or more groups selected from alkyl oxo and hydroxy; R 3 represents alkyl which may optionally be substituted by one of more groups selected from alkoxy, amine, hydroxy and —C(O)Oalkyl; carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl haloalkyl, alkoxy, amine, hydroxy and —C(O)Oalkyl; -alkyl-aryl; -alkyl(aryl) 2 ; -alkyl-heteroaryl; -alkyl(heteroaryl) 2 ; -alkyl(heteroaryl)(aryl); -aryl-O-aryl; aryl; heterocyclyl, -alkyl-C(O)-heterocyclyl, -alkyl-heterocyclyl, -alkyl-C(O)—NR 5 -heterocyclyl or -alkyl(heterocyclyl) 2 in any of which groups heterocyclyl may be optionally substituted by one or more groups selected from alkyl hydroxy and oxo; -heteroaryl; or -hydroxyalkylaryl; R 4 represents H or C 1-3 alkyl; R 5 represents H or C 1-3 alkyl; and X represents O or S.

  本发明涉及式（I）的化合物，其组合物和用于疾病治疗的用途，或其药学上可接受的盐，溶剂或多晶形式，包括其所有互变异构体和立体异构体，其中R1表示杂环芳基；-碳环芳基-杂环芳基；-烯基杂环芳基或-烷基杂环芳基；R2表示烷基，其可以选择性地被羟基取代；碳环芳基，其可以选择性地被一种或多种从烷基和羟基中选择的基团取代；芳基；-芳基-杂环芳基；-杂环芳基-芳基；-芳基-杂环环基；H；杂环芳基；或杂环环基，其可以选择性地被一种或多种从烷基氧化物和羟基中选择的基团取代；R3表示烷基，其可以选择性地被一种或多种从烷氧基，胺基，羟基和-C（O）O烷基中选择的基团取代；碳环芳基，其可以选择性地被一种或多种从烷基卤代烷基，烷氧基，胺基，羟基和-C（O）O烷基中选择的基团取代；-烷基-芳基；-烷基（芳基）2；-烷基-杂环芳基；-烷基（杂环芳基）2；-烷基（杂环芳基）（芳基）；-芳基-O-芳基；芳基；杂环环基，-烷基-C（O）-杂环环基，-烷基-杂环环基，-烷基-C（O）-NR5-杂环环基或-烷基（杂环环基）2，在其中杂环环基可以选择性地被一种或多种从烷基，羟基和氧化物中选择的基团取代；-杂环芳基；或-羟基烷基芳基；R4表示H或C1-3烷基；R5表示H或C1-3烷基；且X表示O或S。
• Inhibitors of glutaminyl cyclase
  申请人：Thormann Michael

  公开号：US08420684B2

  公开（公告）日：2013-04-16

  The present invention relates to compounds of formula (I), combinations and uses thereof for disease therapy, or a pharmaceutically acceptable salt, solvate or polymorph thereof, including all tautomers and stereoisomers thereof wherein R1 represents heteroaryl; -carbocyclyl-heteroaryl; -alkenylheteroaryl or -alkylheteroaryl; R2 represents alkyl which may optionally be substituted by hydroxy; carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl and hydroxy; aryl; -aryl-heteroaryl; -heteroaryl-aryl; -aryl-heterocyclyl; H; heteroaryl; or heterocyclyl, which may optionally be substituted by one or more groups selected from alkyl oxo and hydroxy; R3 represents alkyl which may optionally be substituted by one of more groups selected from alkoxy, amine, hydroxy and —C(O)Oalkyl; carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl haloalkyl, alkoxy, amine, hydroxy and —C(O)Oalkyl; -alkyl-aryl; -alkyl(aryl)2; -alkyl-heteroaryl; -alkyl(heteroaryl)2; -alkyl(heteroaryl)(aryl); -aryl-O-aryl; aryl; heterocyclyl, -alkyl-C(O)-heterocyclyl, -alkyl-heterocyclyl, -alkyl-C(O)—NR5-heterocyclyl or -alkyl(heterocyclyl)2 in any of which groups heterocyclyl may be optionally substituted by one or more groups selected from alkyl hydroxy and oxo; -heteroaryl; or -hydroxyalkylaryl; R4 represents H or C1-3 alkyl; R5 represents H or C1-3 alkyl; and X represents O or S.

  本发明涉及式（I）的化合物，其组合物和用途用于疾病治疗，或其药学上可接受的盐，溶剂或多形体，包括其所有互变异构体和立体异构体，其中R1代表杂环芳基；-碳环芳基-杂环芳基；-烯基杂环芳基或-烷基杂环芳基；R2代表烷基，可以选择性地被羟基取代；碳环芳基，可以选择性地被一个或多个从烷基和羟基中选择的基团取代；芳基；-芳基-杂环芳基；-杂环芳基-芳基；-芳基-杂环芳基；H；杂环芳基；或杂环芳基，可以选择性地被一个或多个从烷基氧代基和羟基中选择的基团取代；R3代表烷基，可以选择性地被一个或多个从烷氧基，胺，羟基和—C（O）O烷基中选择的基团取代；碳环芳基，可以选择性地被一个或多个从烷基卤代烷基，烷氧基，胺，羟基和—C（O）O烷基中选择的基团取代；-烷基-芳基；-烷基（芳基）2；-烷基-杂环芳基；-烷基（杂环芳基）2；-烷基（杂环芳基）（芳基）；-芳基-O-芳基；芳基；杂环芳基，-烷基-C（O）-杂环芳基，-烷基-杂环芳基，-烷基-C（O）-NR5-杂环芳基或-烷基（杂环芳基）2，其中杂环芳基在任何这些基团中可以选择性地被一个或多个从烷基羟基和氧代基中选择的基团取代；-杂环芳基；或-羟基烷基芳基；R4代表氢或C1-3烷基；R5代表氢或C1-3烷基；且X代表氧或硫。
• Ugi Reactions with Ammonia Offer Rapid Access to a Wide Range of 5-Aminothiazole and Oxazole Derivatives
  作者：Mark J. Thompson、Beining Chen

  DOI：10.1021/jo9014529

  日期：2009.9.18

  A series of Ugi reactions has been successfully performed using ammonia as the amine component, employing 2,2,2-trifluoroethanol its a non-nucleophilic solvent in order to suppress known side reactions. Utilizing concentrated aqueous ammonia its it convenient Source, this approach offered a simple, one-step assembly of Ugi adducts suitable for elaboration into it variety of 5-aminoazole compounds through postcondensation modifications. Free or N-substituted 5-aminothiazoles and 5-(trifluoroacetamido)oxazoles were all prepared by this improved methodology. The scope of the synthetic route developed and application of the different products are discussed.