ethyl 3-bromo-3-oxopropionate | 914287-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-bromo-3-oxopropionate
• 英文别名: 2-bromoformylacetic acid ethyl ester；carboethoxyethanoylbromide；ethyl 3-bromo-3-oxopropanoate
• CAS: 914287-88-0
• 化学式: C₅H₇BrO₃
• 分子量: 195.013
• InChiKey: ZDKZSPYOFQFYPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  119-122 °C(Press: 9 Torr)
• 密度：
  1.561±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-bromo-3-oxopropionate 、 2-((tert-butyldimethylsilyl)oxy)aniline 以 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到N-(2-tert-butyldimethylsilyloxyphenyl)malonamic acid ethyl ester
  参考文献：
  名称：

  从禾本科植物中分离和合成化感物质：苯并恶嗪酮和相关化合物。

  摘要：

  自（2H）-1,4-苯并嗪-3（4H）-一骨架的化合物引起了植物化学研究者的关注，因为2,4-二羟基-（2H）-1,4-苯并嗪-3（4H）-一骨架从禾本科（Poaceae）家族的植物中分离出（DIBOA）和2，4-二羟基-7-甲氧基-（2H）-1，4-苯并恶嗪-3（4H）-一（DIMBOA）。这些化合物表现出令人感兴趣的生物学特性，例如植物毒性，抗微生物，拒食，抗真菌和杀虫特性。这些化学物质，除了涉及其代谢，解毒机理以及在农作物土壤和其他系统上的降解所涉及的各种相关化合物之外，还引起了人们的极大兴趣，在某些情况下还具有潜在的农学应用价值。除了一些作者对其化学的贡献外，本文还介绍了对合成观察方法的完整综述。正在进行的对这些化合物潜在的农学实用性的研究正在进行的降解和植物毒性实验需要大量的这些化合物，这些都是从自然资源中获得的。本文提出了一种从Zea mays cv访问DIMBOA的改进方法。

  DOI：

  10.1021/jf050896x

文献信息

• Certain 2,4,5-tri-substituted thiazoles, pharmaceutical compositions
  申请人：Ciba-Geigy Corporation

  公开号：US04451471A1

  公开（公告）日：1984-05-29

  2,4,5-Trisubstituted thiazoles of the formula ##STR1## in which each of R.sub.1 and R.sub.2, independently of the other, represents an aryl or optionally N-oxidized heteroaryl radical each of which is unsubstituted or substituted by aliphatic hydrocarbon radicals, free, etherified or esterified hydroxy, etherified optionally S-oxidized mercapto, aliphatically substituted amino and/or trifluoromethyl, X represents thio, n represents 0, 1, or 2, and R.sub.3 represents an aliphatic hydrocarbon radical that is unsubstituted or substituted by etherified or esterified hydroxy, etherified optionally S-oxidized mercapto and/or, in a position higher than the .alpha.-position, by oxo and/or hydroxy and optionally contains, in addition to terminally bonded hydroxy, sulpho that is present in salt form, or represents an araliphatic hydrocarbon radical that is unsubstituted or substituted in the aryl moiety as indicated for R.sub.1 and R.sub.2, or represents a cycloaliphatic or cycloaliphatic-aliphatic hydrocarbon radical that is unsubstituted or substituted in a position higher than the .alpha.-position by free, etherified or esterified hydroxy, or represents a group of the formula ##STR2## in which m represents, 0, 1 or 2, R.sub.4 represents an aliphatic hydrocarbon radical that is unsubstituted or substituted by etherified or esterified hydroxy, optionally S-oxidized etherified mercapto or, in a position higher than the .alpha.-position and lower than the .omega.-position, by oxo and/or hydroxy and that is optionally interrupted by oxa or thia, which may also be S-oxidized, or, if n and m represent O, represents a direct bond, and R.sub.1 ' and R.sub.2 ' have one of the meanings given for R.sub.1 and R.sub.2, and pharmaceutically acceptable salts thereof are suitable for combating rheumatic disorders, preferably as active ingredients in anti-rheumatic medicaments. The invention relates to medicaments of this type and to non-chemical processes for their manufacture, and also to novel compounds of the formula I and to processes for their manufacture.

  公式为##STR1##的2,4,5-三取代噻唑化合物，其中R.sub.1和R.sub.2中的每一个独立地代表芳基或可选择N-氧化的杂芳基基团，每个基团未取代或被脂肪烃基团、自由、醚化或酯化的羟基、醚化的可选择S-氧化巯基、脂肪烷基取代的氨基和/或三氟甲基取代，X代表硫，n代表0、1或2，R.sub.3代表未取代或被醚化或酯化的羟基、醚化的可选择S-氧化巯基和/或在比α-位置更高的位置上被酮基和/或羟基取代的脂肪烃基团，并且可能除了末端连接的羟基外，还包含以盐形式存在的磺酸基，或者代表未取代或如R.sub.1和R.sub.2所示的芳基基团取代的芳基脂肪烃基团，或者代表未取代或在比α-位置更高的位置上被自由、醚化或酯化的羟基取代的环脂肪或环脂肪-脂肪烃基团，或者代表公式##STR2##中的基团，其中m代表0、1或2，R.sub.4代表未取代或被醚化或酯化的羟基、可选择S-氧化的醚化巯基或在比α-位置和比ω-位置更低的位置上被酮基和/或羟基取代的脂肪烃基团，并且可能被氧杂环或硫杂环中断，该环也可能被S-氧化，或者如果n和m代表O，则代表直接键，R.sub.1'和R.sub.2'具有R.sub.1和R.sub.2给定的含义之一，以及其药学上可接受的盐适用于治疗风湿性疾病，优选作为抗风湿药物中的活性成分。该发明涉及这类药物以及用于其制造的非化学过程，还涉及公式I的新化合物以及其制造方法。
• Pyrazole-4-Carboxamide (YW2065): A Therapeutic Candidate for Colorectal Cancer via Dual Activities of Wnt/β-Catenin Signaling Inhibition and AMP-Activated Protein Kinase (AMPK) Activation
  作者：Wei Yang、Yingjun Li、Yong Ai、Obinna N. Obianom、Dong Guo、Hong Yang、Srilatha Sakamuru、Menghang Xia、Yan Shu、Fengtian Xue

  DOI：10.1021/acs.jmedchem.9b01252

  日期：2019.12.26

  Dysregulation of the Wnt/beta-catenin signaling pathway has been widely recognized as a pathogenic mechanism for colorectal cancer (CRC). Although numerous Wnt inhibitors have been developed, they commonly suffer from toxicity and unintended effects. Moreover, concerns have been raised in targeting this pathway because of its critical roles in maintaining stem cells and regenerating tissues and organs. On the basis of the anthelmintic drug pyrvinium and previous lead FX1128, we have developed a compound YW2065 (1c) which demonstrated excellent anti-CRC effects in vitro and in vivo. YW2065 achieves its inhibitory activity for Wnt signaling by stabilizing Axin-1, a scaffolding protein that regulates proteasome degradation of beta-catenin. Simultaneously, YW2065 also led to the activation of the tumor suppressor AMPK, providing an additional anticancer mechanism. In addition, YW2065 showed favorable pharmacokinetic properties without obvious toxicity. The anti-CRC effect of YW2065 was highlighted by its promising efficacy in a mice xenograft model.
• Isolation and Synthesis of Allelochemicals from Gramineae:  Benzoxazinones and Related Compounds
  作者：Francisco A. Macías、David Marín、Alberto Oliveros-Bastidas、David Chinchilla、Ana M. Simonet、José M. G. Molinillo

  DOI：10.1021/jf050896x

  日期：2006.2.1

  ongoing research into the potential agronomic utility of these compounds required large amounts of them, which were obtained from natural sources. This paper presents a modified methodology to access DIMBOA from Zea mays cv. Apache and to obtain 2-O-beta-D-glucopyranosyl-2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA-Glc) and DIBOA from Secale cereale L. New synthetic methodologies were employed for

  自（2H）-1,4-苯并嗪-3（4H）-一骨架的化合物引起了植物化学研究者的关注，因为2,4-二羟基-（2H）-1,4-苯并嗪-3（4H）-一骨架从禾本科（Poaceae）家族的植物中分离出（DIBOA）和2，4-二羟基-7-甲氧基-（2H）-1，4-苯并恶嗪-3（4H）-一（DIMBOA）。这些化合物表现出令人感兴趣的生物学特性，例如植物毒性，抗微生物，拒食，抗真菌和杀虫特性。这些化学物质，除了涉及其代谢，解毒机理以及在农作物土壤和其他系统上的降解所涉及的各种相关化合物之外，还引起了人们的极大兴趣，在某些情况下还具有潜在的农学应用价值。除了一些作者对其化学的贡献外，本文还介绍了对合成观察方法的完整综述。正在进行的对这些化合物潜在的农学实用性的研究正在进行的降解和植物毒性实验需要大量的这些化合物，这些都是从自然资源中获得的。本文提出了一种从Zea mays cv访问DIMBOA的改进方法。