methyl 2,3-dioxo-3-phenylpropanoate | 86358-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3-dioxo-3-phenylpropanoate
• CAS: 86358-32-9
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: LLGMJHPMHFWMBF-UHFFFAOYSA-N

物化性质

• 沸点：
  298.0±23.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dioxo-3-phenylpropanoate 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.08h， 生成 methyl 3-oxo-2-(phenoxyimino)-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process

  摘要：

  An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.

  DOI：

  10.1021/acs.joc.6b02774
• 作为产物：
  描述：

  methyl 2,3-dihydroxy-3-phenylpropionate 在 4-hydroxy-TEMPO benzoate 、 sodium acetate 、 sodium bromide 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到methyl 2,3-dioxo-3-phenylpropanoate
  参考文献：
  名称：

  Oxidations of Dihydroxyalkanoates to Vicinal Tricarbonyl Compounds with a 4-BzoTEMPO-Sodium Bromite System or by Indirect Electrolysis Using 4-BzoTEMPO and Bromide Ion

  摘要：

  开发了一种高效的方法，从2,3-二羟基烷酸盐获取邻位二氧烷酸盐，这是一种强效竞争性水解酶抑制剂的结构元素。该方法具有一步法程序，并使用可回收的2,2,6,6-四甲基哌啶-1-氧与NaBrO2·3H2O或电生成的活性溴种作为实际氧化剂，且氧化条件温和。

  DOI：

  10.1246/cl.1994.1411

文献信息

• Rapid, Operationally Simple, and Metal-free NBS Mediated One-pot Synthesis of 1,2-Naphthoquinone from 2-Naphthol
  作者：Jaeuk Sim、Hyeju Jo、Mayavan Viji、Minho Choi、Jin-Ah Jung、Heesoon Lee、Jae-Kyung Jung

  DOI：10.1002/adsc.201701312

  日期：2018.3.1

  A metal‐free, one‐pot synthesis of 1,2‐naphthoquinone was accomplished from 2‐naphthol by utilizing economically cheap NBS under open air conditions. Initial formation of 1,1‐dibromonaphthalen‐2‐one and subsequent transformation afforded the 1,2‐naphthoquinone. This oxidation was completed within 30 min and had broad substrate scope. Moreover, this system tolerated heterocyclic systems and was also

  通过在露天条件下利用经济实惠的NBS，由2-萘酚完成了无金属的一锅法合成1,2-萘醌的合成。1,1-二溴萘-2-酮的最初形成和随后的转化提供了1,2-萘醌。该氧化在30分钟内完成，并具有广泛的底物范围。此外，该系统可耐受杂环系统，也适用于1,3-二羰基系统。这种反应时间短，后处理简单且对湿气不敏感的实用方法可能会取代昂贵且有害的氧化剂和金属试剂的使用。
• Displacement of Dinitrogen by Oxygen: A Methodology for the Catalytic Conversion of Diazocarbonyl Compounds to Ketocarbonyl Compounds by 2,6-Dichloropyridine-<i>N</i>-oxide
  作者：Yang Yu、Qiang Sha、Hui Cui、Kory S. Chandler、Michael P. Doyle

  DOI：10.1021/acs.orglett.7b03912

  日期：2018.2.2

  Dirhodium(II) catalyzed dinitrogen extrusion from diazocarbonyl compounds by 2,6-dichloropyridine-N-oxide forms ketocarbonyl compounds in near-quantitative yields. Reactions occur at room temperature, and the pyridine product does not coordinate with dirhodium(II) to inhibit catalysis. Anhydrous tricarbonyl compounds, as well as dicarbonyl compounds, are conveniently prepared by this methodology, and

  重氮（II）催化的重氮通过2,6-二氯吡啶-N-氧化物从重氮羰基化合物中挤出，以接近定量的产率形成酮羰基化合物。反应在室温下发生，并且吡啶产物不与二氢吡啶鎓（II）配位以抑制催化作用。通过这种方法可以方便地制备无水三羰基化合物以及二羰基化合物，并且它们已就地用于催化烯和羟醛的转化。
• Oxidations of Dihydroxyalkanoates to Vicinal Tricarbonyl Compounds with a 4-BzoTEMPO-Sodium Bromite System or by Indirect Electrolysis Using 4-BzoTEMPO and Bromide Ion
  作者：Tsutomu Inokuchi、Ping Liu、Sigeru Torii

  DOI：10.1246/cl.1994.1411

  日期：1994.8

  An efficient access to vicinal dioxoalkanoates, one of structural elements of potent competitive inhibitors of hydrolytic enzyme, from 2,3-dihydroxyalkanoates has been developed, which features an one-step procedure with a mild oxidizing system using recyclable 2,2,6,6-tetramethylpiperidine-1-oxyl in combination with NaBrO2·3H2O or electrogenerated active bromine species as a real oxidant.

  开发了一种高效的方法，从2,3-二羟基烷酸盐获取邻位二氧烷酸盐，这是一种强效竞争性水解酶抑制剂的结构元素。该方法具有一步法程序，并使用可回收的2,2,6,6-四甲基哌啶-1-氧与NaBrO2·3H2O或电生成的活性溴种作为实际氧化剂，且氧化条件温和。
• Addition of Mixed (Alkenyl)dialkylzincates to Vicinal Diketo Esters
  作者：Lars Selter、Klaus Harms、Ulrich Koert

  DOI：10.1002/ejoc.201601598

  日期：2017.2.24

  Methods for the regioselective alkylation, arylation and alkenylation of α,β-diketoesters using organozinc reagents are reported. Alkylation and arylation in α-position is possible using diorgano zinc compounds. Alkenylation can be achieved using mixed alkenyl-dineopentyl zincates.

  报道了使用有机锌试剂对 α,β-二酮酯进行区域选择性烷基化、芳基化和烯基化的方法。使用二有机锌化合物可以在 α 位进行烷基化和芳基化。使用混合的烯基-二新戊基锌酸盐可以实现烯基化。
• <i>p</i>-TSA-catalyzed a simple and efficient one-pot eco-friendly synthesis of functionalized new isoxazolyl-4-hydroxyindole-3-carboxylate derivatives in aqueous medium
  作者：Nallamothu Vanaja Rani、Ravindhranath Kunta

  DOI：10.1080/00397911.2020.1825743

  日期：2021.1.17

  A simple, efficient, cost-effective and one-pot eco-friendly protocol has been developed for the synthesis of new isoxazolyl-4-hydroxyindole-3-carboxylate derivatives by using 4-amino-3-methyl-5-st...

  使用 4-amino-3-methyl-5-st 合成新的异恶唑基-4-羟基吲哚-3-羧酸衍生物，开发了一种简单、高效、经济且一锅法的环保方案。