methyl 2-methyl-3-(4-nitrophenyl)-3-oxopropanoate | 1097259-10-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-methyl-3-(4-nitrophenyl)-3-oxopropanoate
• 英文别名: methyl 3-(4-nitrophenyl)-2-methyl-3-oxopropanoate
• CAS: 1097259-10-3
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: CNFPRQCHQJVTJW-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  337.9±17.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-3-(4-nitrophenyl)-3-oxopropanoate 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以95%的产率得到4-methyl-5-(4-nitrophenyl)-2,3-dihydro-1H-pyrazol-3-one
  参考文献：
  名称：

  Morita–Baylis–Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI–MS(/MS)

  摘要：

  We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring.

  DOI：

  10.1007/s00706-015-1427-6
• 作为产物：
  描述：

  2-[羟基-(4-硝基-苯基)-甲基]-丙烯酸甲酯 在 tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以84%的产率得到methyl 2-methyl-3-(4-nitrophenyl)-3-oxopropanoate
  参考文献：
  名称：

  五甲基环戊二烯钌：一种有效的催化剂，可将官能化的烯丙基醇氧化还原为羰基化合物

  摘要：

  报道了钌（II）络合物[RuCp *（CH 3 CN）3 ] [PF 6 ] 1在乙腈中将烯丙醇转化为羰基化合物的催化活性。已证明该催化剂能够在光滑条件下催化反应性差和/或功能化的底物的转化。

  DOI：

  10.1016/j.tet.2008.09.095

文献信息

• Pentamethylcyclopentadienyl ruthenium: an efficient catalyst for the redox isomerization of functionalized allylic alcohols into carbonyl compounds
  作者：Asmae Bouziane、Bertrand Carboni、Christian Bruneau、François Carreaux、Jean-Luc Renaud

  DOI：10.1016/j.tet.2008.09.095

  日期：2008.12

  The catalytic activity of the ruthenium(II) complex [RuCp∗(CH3CN)3][PF6] 1 in the transposition of allylic alcohols into carbonyl compounds, in acetonitrile, is reported. This catalyst has proven to be able to catalyze the transformation of poorly reactive and/or functionalized substrates under smooth conditions.

  报道了钌（II）络合物[RuCp *（CH 3 CN）3 ] [PF 6 ] 1在乙腈中将烯丙醇转化为羰基化合物的催化活性。已证明该催化剂能够在光滑条件下催化反应性差和/或功能化的底物的转化。
• Palladium-Catalyzed Carbonylation/Acyl Migratory Insertion Sequence
  作者：Zhenhua Zhang、Yiyang Liu、Mingxing Gong、Xiaokun Zhao、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.200906349

  日期：2010.2.1

  On the move: A palladium‐catalyzed reaction of aryl iodides, diazo compounds or N‐tosylhydrazones, and carbon monoxide affords β‐oxo esters or ketones/enones (see scheme; DCE=1,2‐dichloroethane). The products are delivered with high efficiency through the title sequence.

  进展中：芳基碘化物，重氮化合物或N-甲苯磺酰hydr与一氧化碳的钯催化反应可制得β-氧代酯或酮/烯酮（参见方案； DCE = 1,2-二氯乙烷）。产品通过标题顺序高效交付。
• RIBOSOME-MEDIATED INCORPORATION OF PEPTIDES AND PEPTIDOMIMETICS
  申请人：Arizona Board of Regents on Behalf of Arizona State University

  公开号：US20180002709A1

  公开（公告）日：2018-01-04

  Modified ribosomes that were selected using a dipeptidyl-puromycin aminonucleoside are used to mediate site-specific incorporation of one or more peptides and peptidomimetics into protein in a cell free translation system. In addition, new fluorescent dipeptidomimetics have been synthesized and incorporated into proteins, as well as modified proteins containing one or more non-naturally occurring dipeptides.
• Morita–Baylis–Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI–MS(/MS)
  作者：Rosimeire C. Barcelos、Lucas A. Zeoly、Manoel T. Rodrigues、Bruno R. V. Ferreira、Marcos N. Eberlin、Fernando Coelho

  DOI：10.1007/s00706-015-1427-6

  日期：2015.9

  We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring.