2-(2-oxopropoxy)acetic acid | 1219037-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-oxopropoxy)acetic acid
• CAS: 1219037-51-0
• 化学式: C₅H₈O₄
• mdl: MFCD19231901
• 分子量: 132.116
• InChiKey: AONOZBGBRAWBEC-UHFFFAOYSA-N

物化性质

• 沸点：
  312.1±17.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-oxopropoxy)acetic acid 在 盐酸 、 氯化铵 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  New nitrofurans amenable by isocyanide multicomponent chemistry are active against multidrug-resistant and poly-resistant Mycobacterium tuberculosis

  摘要：

  A set of structurally diverse N-amino delta-lactams decorated with a 5-nitro-2-furyl moiety was synthesized using isocyanide-based multicomponent chemistry and evaluated for antibacterial activity. Three compounds displayed a selective and potent (MIC 22-33 mu M) inhibition of M. tuberculosis H(37)Rv strain growth, while other Gram-positive (MRSA and E. faecium) or Gram-negative (E. coli, P. aeruginosa, A. baumannii, K. pneumoniae) pathogens were not affected. The compounds also displayed moderate low cytotoxicity, as demonstrated in cell line viability assays. Several multidrug-and poly-resistant patient-derived M. tuberculosis strains were found to be susceptible to treatment with these compounds. The three most potent compounds share a significant structural similarity which provides a basis for further scaffold-hopping analog design. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.003
• 作为产物：
  描述：

  ethyl 2-(2-oxopropoxy)acetate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以85%的产率得到2-(2-oxopropoxy)acetic acid
  参考文献：
  名称：

  Proline-like β-turn mimics accessed via Ugi reaction involving monoprotected hydrazines

  摘要：

  A four-center, three-component Ugi-type reaction of a variety of keto acids, Boc- or Cbz-protected hydrazine, and isocyanides offers a simple and high yielding access to cyclic products containing an N-aminolactam unit. The latter are shown to form consistently an intramolecular hydrogen bond leading to a p-turn-like secondary structure. The possibility of integrating such N-aminolactam units (without disruption of the folded structure) into pseudotripeptide fragments is demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.141

文献信息

• Transition metal-free one-pot cascade synthesis of 7-oxa-2-azatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-3-ones from biomass-derived levulinic acid under mild conditions
  作者：Amitabh Jha、Ajaya B. Naidu、Ashraf M. Abdelkhalik

  DOI：10.1039/c3ob41826j

  日期：——

  An efficient, environmentally benign, transition-metal free, tandem C–N, C–O bond formation reaction is developed for the synthesis of tricyclic 7-oxa-2-azatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-3-ones and their homologs from easily available starting materials, including renewable levulinic acid, a keto acid. The reaction of keto acids with methyl chloroformate and variously substituted o-aminobenzyl alcohols using triethylamine as a base in toluene at room temperature gave good to excellent yields. This newly developed protocol was successfully utilized for the synthesis of a variety of polycyclic 7-oxa-2-azatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-3-ones and related compounds.

  开发了一种高效、环境友好、无需过渡金属的串联C-N、C-O键形成反应，用于从易于获得的起始原料，包括可再生的乙酰乙酸，一种酮酸，合成三环7-氧杂-2-氮杂三环[7.4.0.0²,6]十三碳-1(9),10,12-三烯-3-酮及其同系物。酮酸与氯甲酸甲酯和各种取代的邻氨基苄醇在甲苯中室温下使用三乙胺作为碱进行反应，产率良好至优秀。这一新开发的方案成功地应用于合成多种多环7-氧杂-2-氮杂三环[7.4.0.0²,6]十三碳-1(9),10,12-三烯-3-酮及相关化合物。
• New nitrofurans amenable by isocyanide multicomponent chemistry are active against multidrug-resistant and poly-resistant Mycobacterium tuberculosis
  作者：Mikhail Krasavin、Vladislav Parchinsky、Grigory Kantin、Olga Manicheva、Marine Dogonadze、Tatiana Vinogradova、Bianka Karge、Mark Brönstrup

  DOI：10.1016/j.bmc.2017.02.003

  日期：2017.3

  A set of structurally diverse N-amino delta-lactams decorated with a 5-nitro-2-furyl moiety was synthesized using isocyanide-based multicomponent chemistry and evaluated for antibacterial activity. Three compounds displayed a selective and potent (MIC 22-33 mu M) inhibition of M. tuberculosis H(37)Rv strain growth, while other Gram-positive (MRSA and E. faecium) or Gram-negative (E. coli, P. aeruginosa, A. baumannii, K. pneumoniae) pathogens were not affected. The compounds also displayed moderate low cytotoxicity, as demonstrated in cell line viability assays. Several multidrug-and poly-resistant patient-derived M. tuberculosis strains were found to be susceptible to treatment with these compounds. The three most potent compounds share a significant structural similarity which provides a basis for further scaffold-hopping analog design. (C) 2017 Elsevier Ltd. All rights reserved.
• Proline-like β-turn mimics accessed via Ugi reaction involving monoprotected hydrazines
  作者：Mikhail Krasavin、Vladislav Parchinsky、Alexei Shumsky、Igor Konstantinov、Anton Vantskul

  DOI：10.1016/j.tetlet.2009.12.141

  日期：2010.3

  A four-center, three-component Ugi-type reaction of a variety of keto acids, Boc- or Cbz-protected hydrazine, and isocyanides offers a simple and high yielding access to cyclic products containing an N-aminolactam unit. The latter are shown to form consistently an intramolecular hydrogen bond leading to a p-turn-like secondary structure. The possibility of integrating such N-aminolactam units (without disruption of the folded structure) into pseudotripeptide fragments is demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.