2-氧代-3-(吡啶-2-基)丙酸甲酯 | 94832-92-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-氧代-3-(吡啶-2-基)丙酸甲酯
• 英文名称: methyl 2-oxo-3-(pyridin-2-yl)propanoate
• 英文别名: alpha-Oxopyridine-2-propanoic acid methyl ester；methyl 2-oxo-3-pyridin-2-ylpropanoate
• CAS: 94832-92-5
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: GUYRUKAOOXUUFV-UHFFFAOYSA-N

物化性质

• 沸点：
  290.1±23.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氧代-3-(吡啶-2-基)丙酸甲酯 在 sodium tetrahydroborate 作用下， 生成 NSC 49848
  参考文献：
  名称：

  Enantiomerically Pure 3-Aryl- and 3-Hetaryl-2-hydroxypropanoic Acids by Chemoenzymatic Reduction of 2-Oxo Acids

  摘要：

  Phenyllactic acids are found in numerous natural products as well as in active substances used in medicine or plant protection. Enantiomerically pure phenyllactic acids are available by transition-metal-catalyzed hydrogenations or chemoenzymatic reductions of the corresponding 3-aryl-2-oxopropanoic acids. We show here that d-lactate dehydrogenase from Staphylococcus epidermidis reduces a broad spectrum of 2-oxo acids, which are difficult substrates for transition-metal-catalyzed reactions, with excellent enantioselectivities in a simple experimental setup.

  DOI：

  10.1021/jo502529g
• 作为产物：
  描述：

  (Z)-3-Pyridin-2-yl-2-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonyloxy)-acrylic acid methyl ester 在 4-二甲氨基吡啶 甲醇 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到2-氧代-3-(吡啶-2-基)丙酸甲酯
  参考文献：
  名称：

  一种由醛合成α-酮酸酯的简便方法

  摘要：

  描述了醛到α-酮酸酯的有效的两步，两次碳同系化。

  DOI：

  10.1016/s0040-4039(01)91067-6

文献信息

• α-Functionalization of Ketones via a Nitrogen Directed Oxidative Umpolung
  作者：Gabriel M. Kiefl、Tanja Gulder

  DOI：10.1021/jacs.0c10700

  日期：2020.12.9

  methods available today, overcoming the inherent reactivity still remains a constant challenge in organic chemistry. The oxidative α-functionalization of ketones by external nucleophiles constitute such an example. Herein, we present a hypervalent F-iodane mediated umpolung of pyridyl ketones triggered by Lewis base/Lewis acid noncovalent interactions. A wide variety of external nucleophiles are introduced

  反转分子中的极性是扩展结构空间边界的通用工具。尽管今天有多种不同的 umpolung 方法可用，但克服固有的反应性仍然是有机化学中的一个持续挑战。外部亲核试剂对酮的氧化 α-官能化构成了这样一个例子。在本文中，我们提出了一种由路易斯碱/路易斯酸非共价相互作用触发的高价氟碘烷介导的吡啶基酮的umpolung。应用这种底物导向概念，以高区域选择性引入了多种外部亲核试剂。
• A mild preparation of substituted indolizines and indole from simple aromatic precursors using (trimethylsilyl)diazomethane
  作者：Liusheng Zhu、Marc Vimolratana、Sean P. Brown、Julio C. Medina

  DOI：10.1016/j.tetlet.2008.01.067

  日期：2008.3

  A mild and convenient synthesis of substituted indolizines from readily available 2-(pyridin-2-yl)acetyl derivatives using (trimethylsilyl)diazomethane is described. The extension of this methodology to the synthesis of indole from 2-aminobenzaldehyde is also reported.

  描述了使用（三甲基甲硅烷基）重氮甲烷由容易获得的2-（吡啶-2-基）乙酰基衍生物温和方便地合成取代的吲哚嗪的方法。还报道了该方法的扩展到由2-氨基苯甲醛合成吲哚。
• HORNE, D.;GAUDINO, J.;THOMPSON, W. J., TETRAHEDRON LETT., 1984, 25, N 33, 3529-3532
  作者：HORNE, D.、GAUDINO, J.、THOMPSON, W. J.

  DOI：——

  日期：——
• A convenient method for the synthesis of α-Ketoesters from aldehydes
  作者：David Horne、John Gaudino、Wayne J. Thompson

  DOI：10.1016/s0040-4039(01)91067-6

  日期：1984.1

  An efficient two step, two carbon homologation of aldehydes to α-ketoesters is described.

  描述了醛到α-酮酸酯的有效的两步，两次碳同系化。
• Enantiomerically Pure 3-Aryl- and 3-Hetaryl-2-hydroxypropanoic Acids by Chemoenzymatic Reduction of 2-Oxo Acids
  作者：Sivatharushan Sivanathan、Florian Körber、Jannis Aron Tent、Svenja Werner、Jürgen Scherkenbeck

  DOI：10.1021/jo502529g

  日期：2015.3.6

  Phenyllactic acids are found in numerous natural products as well as in active substances used in medicine or plant protection. Enantiomerically pure phenyllactic acids are available by transition-metal-catalyzed hydrogenations or chemoenzymatic reductions of the corresponding 3-aryl-2-oxopropanoic acids. We show here that d-lactate dehydrogenase from Staphylococcus epidermidis reduces a broad spectrum of 2-oxo acids, which are difficult substrates for transition-metal-catalyzed reactions, with excellent enantioselectivities in a simple experimental setup.