3-methyl-5-oxo-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester | 146037-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-5-oxo-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester
• 英文别名: 3-Methyl-5-oxo-2,5-dihydro-isoxazol-4-carbonsaeure-aethylester；ethyl 3-methyl-5-oxo-2H-1,2-oxazole-4-carboxylate
• CAS: 146037-86-7
• 化学式: C₇H₉NO₄
• 分子量: 171.153
• InChiKey: QLNYORXNSOZGSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-5-oxo-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 硝基苯 为溶剂， 25.0~140.0 ℃ 、310.27 kPa 条件下， 反应 1.0h， 生成 ethyl 3-<(isoquinolin-1-yl)amino>but-2-enoate
  参考文献：
  名称：

  Singh, Yogendra; Prager, Rolf H., Australian Journal of Chemistry, 1992, vol. 45, # 11, p. 1811 - 1823

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二甲基-4-氧代-吡喃-3,5-二羧酸二乙酯 在 水 、 羟胺 、 sodium carbonate 作用下， 生成 3-methyl-5-oxo-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Palazzo, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1902, vol. <5> 11 I, p. 563

  摘要：

  DOI：

文献信息

• Chemistry of 5-oxodihydroisoxazoles. Part 17.1 Acylation of 5-oxodihydroisoxazoles
  作者：Rolf H. Prager、Jason A. Smith、Ben Weber、Craig M. Williams

  DOI：10.1039/a700133i

  日期：——

  2-Unsubstituted isoxazol-5(4H)-ones and -5(2H)-ones may be acylated by acid chlorides, anhydrides or carboxylic acids in the presence of carbodiimides, to give O- and N-acylated products. The solvent, the presence of base and the temperature are found to alter the product ratios dramatically, but the substituents present at C-3 have the greatest effect. Aliphatic acid anhydrides and chlorides generally react at nitrogen, but aroyl halides give significant proportions of O-acylated products. Limited success in converting O-aroyl to N-aroyl isoxazolones is reported.

  未取代的异恶唑-5(4H)-酮和-5(2H)-酮可以通过在碳二亚胺存在下与酰氯、酸酐或羧酸反应进行酰化，生成O-和N-酰化产物。溶剂、碱的存在以及反应温度都会显著影响产物比例，但C-3位上的取代基影响最大。脂肪族酸酐和酰氯通常在氮原子上反应，而芳氧基酰氯则会产生大量O-酰化产物。关于将O-芳酰基转化为N-芳酰基异恶唑酮的报道中，成功案例有限。
• The Synthesis of Some Chiral 2-Aminoalkyloxazole-5-carboxylates from Isoxazol-5(2H)-ones
  作者：Matthew Cox、Rolf H. Prager、Carina E. Svensson、Max R. Taylor

  DOI：10.1071/ch03053

  日期：——

  Ethyl 5-oxo-2,5-dihydroisoxazole-4-carboxylates have been N-acylated by a number of natural and synthetic phthalimidylamino acids in the presence of carbodiimides. The N-acylated products form the corresponding 2-aminoalkyloxazole-5-carboxylates smoothly when irradiated at 300 nm in acetone.

  在碳二亚胺存在下，5-氧代-2,5-二氢异恶唑-4-羧酸乙酯已被许多天然和合成的邻苯二甲酰亚胺基氨基酸 N-酰化。当在丙酮中以 300 nm 照射时，N-酰化产物会顺利形成相应的 2-氨基烷基恶唑-5-羧酸盐。
• Inhibitors of the Hiv Integrase Enzyme
  申请人：Dress Ruprecht Klaus

  公开号：US20070232644A1

  公开（公告）日：2007-10-04

  The present invention relates to compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof, pharmaceutical compositions comprising compounds of formula (I), and their methods of use in treating HIV-infected mammals.

  本发明涉及公式(I)的化合物，或其药学上可接受的盐或溶剂，包括公式(I)的化合物的制药组合物，以及它们在治疗感染HIV的哺乳动物中的使用方法。
• INHIBITORS OF THE HIV INTEGRASE ENZYME
  申请人：Dress Klaus Ruprecht

  公开号：US20090170846A1

  公开（公告）日：2009-07-02

  The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus “HIV” integrase enzyme. Formula (I).

  本发明涉及公式（I）的化合物，以及其制备的药用可接受的盐和溶剂，以及它们作为人类免疫缺陷病毒“HIV”整合酶酶的调节剂或抑制剂的用途。公式（I）。
• A new synthesis of chiral aminoalkyloxazolecarboxylate esters from isoxazol-5(2H)-ones: the synthesis of almazoles A and B
  作者：Jabbar Khalafy、Carina E. Svensson、Rolf H. Prager、Craig M. Williams

  DOI：10.1016/s0040-4039(98)01014-4

  日期：1998.7

  2-(1-Aminoalkyl)oxazole-4 and 5-carboxylates are available, without detectable racemisation, by a sequence involving N-acylation of isoxazol-5(2H)one carboxylates with phthalimidoamino acids, photolysis of the acylated product, and hydrazinolysis. An application of the procedure to the synthesis of almazole A and B is described (C) 1998 Elsevier Science Ltd. All rights reserved.