n-propyl glyoxylate | 925-61-1

• 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: n-propyl glyoxylate
• 英文别名: Propyl 2-oxoacetate
• CAS: 925-61-1
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: BWQSEDZTBKYDHS-UHFFFAOYSA-N

物化性质

• 沸点：
  149.6±23.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 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：

  n-propyl glyoxylate 在 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以62%的产率得到n-propyl 2-oxo-2-((2-oxo-2-propoxyethyl)amino)acetate
  参考文献：
  名称：

  发现氧化还原系统使C–N–C键形成：前所未有的Aza-Cannizzaro反应

  摘要：

  描述了涉及乙醛酸酯原位氧化还原转化为甘氨酸的新型反应。简单的原料和合成甘氨酸衍生物的温和条件可能表明了通往益生元化学的途径。该过程类似于涉及氨的坎尼扎罗反应，因此可以称为分子内Aza-Cannizzaro型反应。借助计算分析详细检查了该反应，以证实所提出的机理。

  DOI：

  10.1016/j.tetlet.2017.04.010
• 作为产物：
  描述：

  di-n-propyl tartrate 在 过碘酸 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 n-propyl glyoxylate
  参考文献：
  名称：

  Superoxide dismutase mimetics. Part 2: synthesis and structure–Activity relationship of glyoxylate- and glyoxamide-Derived metalloporphyrins

  摘要：

  Novel glyoxylate- and glyoxamide-derived metalloporphyrins 26-58 were synthesized and evaluated as potential superoxide dismutase (SOD) mimetics. Relative to previously studied MnTBAP analogues, the glyoxylate-derived metalloporphyrins 32, 39, and 54 and glyoxamide-derived metalloporphyrin 49, exhibited enhanced activity in the SOD assay and the majority of the analogues in the current series showed enhanced inhibition of lipid peroxidation and catalase activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00272-4

文献信息

• Perfluorosulfonylmethide compounds; use thereof for carbon-carbon bond formation
  申请人：The Institute of Applied Catalysis

  公开号：US06664380B1

  公开（公告）日：2003-12-16

  Free perfluorosulfonylmethide compounds and metal salts thereof show strong catalytic activity in carbon-carbon bond formation reactions, in amounts as low as 0.1 mole %. Fluorous media may be used, especially biphasic fluorous media enabling ready recycling of the catalyst. The formula thereof is: M[C(SO2R1)3−(m+q)(SO2R2)m(SO2R3)q]x where M is H, Sc, Y, La, Ce, Pr, Nd, Sm Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, Al, Ga, In or Tl, x is the common oxidation state of a said metal M, R1, R2 and R3 are perfluorinated or polyfluoronated hydrocarbon, ether or amine moieties or mixtures thereof and m+q=0, 1, 2 or 3 (m and q being zero or integers).

  氟代磺酰甲基化合物及其金属盐在碳-碳键形成反应中表现出强大的催化活性，即使含量低至0.1摩尔％。可以使用氟介质，特别是双相氟介质，可实现催化剂的便捷循环利用。其化学式为：M［C(SO2R1)3−(m+q)(SO2R2)m(SO2R3)q］x，其中M为H、Sc、Y、La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Ho、Er、Tm、Yb、Lu、Zr、Hf、Th、Nb、Ta、U、Bi、Al、Ga、In或Tl，x为所述金属M的常见氧化态，R1、R2和R3为全氟或多氟烃、醚或胺基团或其混合物，m+q=0、1、2或3（m和q为零或整数）。
• Rationalisation of the stereochemical outcome of ene-reductase-mediated bioreduction of α,β-difunctionalised alkenes
  作者：Elisabetta Brenna、Michele Crotti、Francesco G. Gatti、Alessia Manfredi、Daniela Monti、Fabio Parmeggiani、Andrea Pugliese、Davila Zampieri

  DOI：10.1016/j.molcatb.2013.12.020

  日期：2014.3

  The OYE1-3-mediated reductions of some alpha,beta-difunctionalised alkenes, showing on the double bond a nitrile and ester group, are submitted to a careful stereochemical analysis, in order to identify which of the two electron-withdrawing groups (EWGs) is responsible for the activation of the C=C double bond towards reduction and for establishing hydrogen bond interactions within the binding pocket of the enzymes. The results show that for most of these substrates the activating EWG is the CN moiety linked to the prostereogenic olefinic carbon atom. The final stereochemical outcome can be explained through the empirical model which has been recently developed for difunctionalised alkenes activated by carbonyl/carboxyl containing EWGs.In a single case the activation is due to the COOR group linked to the less substituted olefinic carbon atom: an alternative empirical model is established for this kind of substrates, taking into consideration the OYE-catalysed reductions of beta,beta'-disubstituted-a-monofunctionalised alkenes. (C) 2014 Elsevier B.V. All rights reserved.
• Fourneau,J.-P. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 272, p. 1515 - 1517
  作者：Fourneau,J.-P. et al.

  DOI：——

  日期：——
• MIKAMI, KOICHI;LOHTECK-PENG;NAKAI, TAKESHI, TETRAHEDRON LETT., 29,(1988) N 48, C. 6305-6308
  作者：MIKAMI, KOICHI、LOHTECK-PENG、NAKAI, TAKESHI

  DOI：——

  日期：——
• Superoxide dismutase mimetics. Part 2: synthesis and structure–Activity relationship of glyoxylate- and glyoxamide-Derived metalloporphyrins
  作者：Michael P Trova、Polivina Jolicia F Gauuan、Anthony D Pechulis、Stephen M Bubb、Stephen B Bocckino、James D Crapo、Brian J Day

  DOI：10.1016/s0968-0896(03)00272-4

  日期：2003.7

  Novel glyoxylate- and glyoxamide-derived metalloporphyrins 26-58 were synthesized and evaluated as potential superoxide dismutase (SOD) mimetics. Relative to previously studied MnTBAP analogues, the glyoxylate-derived metalloporphyrins 32, 39, and 54 and glyoxamide-derived metalloporphyrin 49, exhibited enhanced activity in the SOD assay and the majority of the analogues in the current series showed enhanced inhibition of lipid peroxidation and catalase activity. (C) 2003 Elsevier Science Ltd. All rights reserved.