2-苄基-3-乙氧基-3-氧代丙酸钾 | 85969-93-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 2-苄基-3-乙氧基-3-氧代丙酸钾
• 英文名称: potassium 2-benzyl-3-ethoxy-3-oxopropanoate
• 英文别名: benzyl-malonic acid monoethyl ester; potassium-salt；Benzyl-malonsaeure-monoaethylester; Kalium-Salz；potassium;2-benzyl-3-ethoxy-3-oxopropanoate
• CAS: 85969-93-3
• 化学式: C₁₂H₁₃O₄*K
• 分子量: 260.331
• InChiKey: CYHGJONOFZIPGC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.84
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.43
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-苄基-3-乙氧基-3-氧代丙酸钾 在 溴 、 三乙胺 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 肉桂酸乙酯
  参考文献：
  名称：

  通过丙二酸的半酯制备α-溴酸酯的一种在温和条件下快速脱羧的新方法

  摘要：

  高产率地制备了α-溴丙二酸半酯，发现在温和条件下，使用碳酸锂在回流的四氢呋喃中，α-溴丙二酸半酯迅速脱羧为α-溴酸酯。

  DOI：

  10.1016/s0040-4039(00)81355-6
• 作为产物：
  描述：

  苄基丙二酸二乙酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以91%的产率得到2-苄基-3-乙氧基-3-氧代丙酸钾
  参考文献：
  名称：

  通过丙二酸的半酯制备α-溴酸酯的一种在温和条件下快速脱羧的新方法

  摘要：

  高产率地制备了α-溴丙二酸半酯，发现在温和条件下，使用碳酸锂在回流的四氢呋喃中，α-溴丙二酸半酯迅速脱羧为α-溴酸酯。

  DOI：

  10.1016/s0040-4039(00)81355-6

文献信息

• Access to β-Keto Esters by Palladium-Catalyzed Carbonylative Coupling of Aryl Halides with Monoester Potassium Malonates
  作者：Signe Korsager、Dennis U. Nielsen、Rolf H. Taaning、Troels Skrydstrup

  DOI：10.1002/anie.201304072

  日期：2013.9.9

  New tricks for an old dog: The Pd‐catalyzed carbonylative α‐arylation of monoethyl potassium malonates with aryl bromides and reactive aryl chlorides provides a simple and direct route to aryl β‐ketoesters. Because only stoichiometric amounts of carbon monoxide are employed, the method is ideal for the introduction of carbon isotopes into more complex structures.

  老狗的新招数：丙二酸单乙酯钾的Pd催化羰基α-芳基化与芳基溴化物和反应性芳基氯化物的合成提供了一条简单而直接的途径制备芳基β-酮酸酯。由于仅使用化学计量的一氧化碳，因此该方法非常适合将碳同位素引入更复杂的结构中。
• Synthesis of maculalactone A and derivatives for environmental fate tracking studies
  作者：Samuel L. Bader、Michael U. Luescher、Karl Gademann

  DOI：10.1039/c4ob02042a

  日期：——

  Labelled probes of the antifouling natural product, maculalactone A, allow for distribution studies in Artemia salina.

  标记的抗污染天然产物maculalactone A的探针，可用于在盐水蝦中进行分布研究。
• Design and Synthesis of Malonic Acid-Based Inhibitors of Human Neutrophil Collagenase (MMP8)
  作者：Erich Graf von Roedern、Frank Grams、Hans Brandstetter、Luis Moroder

  DOI：10.1021/jm9706426

  日期：1998.1.1

  For most of the known synthetic inhibitors of matrix metalloproteinases (MMPs), a substrate-like binding mode was postulated on the basis of X-ray crystallographic structures of MMP/inhibitor complexes. Conversely, the malonic acid-based inhibitor (2R,S)-HONH-CO-CH(i-Bu)-CO-Ala-Gly-NH2 was found to bind in a surprisingly different manner. Using this compound as a new lead structure, the interaction sites with human neutrophil collagenase (MMP8) were optimized with a series of iteratively designed analogues and with the help of X-ray structural analysis of selected inhibitors to finally produce low molecular weight nonpeptidic compounds of 500-1000-fold improved inhibitory potency.
• Manganese(III)-mediated tandem oxidative cyclizations of .beta.-diesters. Influence of copper(II) upon the chemoselectivity of the reaction
  作者：M. P. Bertrand、J. M. Surzur、H. Oumar-Mahamat、C. Moustrou

  DOI：10.1021/jo00009a031

  日期：1991.4

  Mn(III)-mediated oxidative cyclization of esters derived from allylmalonic and benzylmalonic acids afforded through two consecutive cyclizations bislactones (17, 5) and bicyclic lactones (19, 21) or tricyclic lactones (7, 9). The ratio of these products is controlled by the stereoselectivity of the first step involving the intramolecular addition of a carbon-centered radical to a double bond. Oxidations conducted either in the presence of stoichiometric cupric ion or without added Cu(II) provide a comprehensive view of the respective influences of Mn(III) and Cu(II) upon the chemoselectivity of the reaction, which are related to their ability to oxidize radicals of different classes. For example, the primary and secondary radicals 3a and 3b, which are not efficiently oxidized by Mn(III), undergo cyclization leading to the trans fused tricyclic gamma-lactones 9a and 9b exclusively in the absence of cupric ion.
• BERTRAND, M. P.;SURZUR, J. M.;OUMAR-MAHAMAT, H.;MOUSTROU, C., J. ORG. CHEM., 56,(1991) N, C. 3089-3097
  作者：BERTRAND, M. P.、SURZUR, J. M.、OUMAR-MAHAMAT, H.、MOUSTROU, C.

  DOI：——

  日期：——