2,2-dimethyl-5-(2-nitro-1-phenylethyl)-1,3-dioxane-4,6-dione | 864294-75-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-5-(2-nitro-1-phenylethyl)-1,3-dioxane-4,6-dione
• CAS: 864294-75-7
• 化学式: C₁₄H₁₅NO₆
• 分子量: 293.276
• InChiKey: XTUFMIJJOUMASE-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86 °C
• 沸点：
  540.8±45.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-(2-nitro-1-phenylethyl)-1,3-dioxane-4,6-dione 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 4-苯基-2-吡咯烷酮
  参考文献：
  名称：

  New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

  摘要：

  A new approach based on multicomponent/domino combined reactions for the synthesis of gamma-nitroesters promoted by a mixed aluminium-magnesium oxides derived from hydrotalcite-like material was developed. Different gamma-nitroesters were synthesized in 15-95% yield using Meldrum's acid, aromatic aldehydes, nitromethane and different alcohols as reagents and solvents. The gamma-aminobutyric acid derivatives, Phenibut and Baclofen, were prepared in 63 and 61% overall yield, respectively, through a two steps synthetic strategy. A mechanistic pathway was proposed based on the gas chromatography mass spectrometry (GC-MS) and electrospray ionization mass spectrometry (ESI-MS) experiments.

  DOI：

  10.5935/0103-5053.20160175
• 作为产物：
  描述：

  1-苯基-2-硝基乙醇 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 2,2-dimethyl-5-(2-nitro-1-phenylethyl)-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

  摘要：

  A new approach based on multicomponent/domino combined reactions for the synthesis of gamma-nitroesters promoted by a mixed aluminium-magnesium oxides derived from hydrotalcite-like material was developed. Different gamma-nitroesters were synthesized in 15-95% yield using Meldrum's acid, aromatic aldehydes, nitromethane and different alcohols as reagents and solvents. The gamma-aminobutyric acid derivatives, Phenibut and Baclofen, were prepared in 63 and 61% overall yield, respectively, through a two steps synthetic strategy. A mechanistic pathway was proposed based on the gas chromatography mass spectrometry (GC-MS) and electrospray ionization mass spectrometry (ESI-MS) experiments.

  DOI：

  10.5935/0103-5053.20160175

文献信息

• Asymmetric organocatalytic Michael addition of Meldrum’s acid to nitroalkenes: probing the mechanism of bifunctional thiourea organocatalysts
  作者：Ari M.P. Koskinen、Antti O. Kataja

  DOI：10.3998/ark.5550190.0011.216

  日期：——

  The asymmetric Michael addition of Meldrum’s acid to nitroalkenes was studied using a novel type of Cinchona alkaloid-based bifunctional thiourea organocatalyst. The functionality of the thiourea catalysts was also probed by preparing and testing thiourea-N-methylated analogues of the well-known bis-(3,5-trifluoromethyl)phenyl-substituted catalyst.

  使用一种新型的基于金鸡纳生物碱的双功能硫脲有机催化剂，研究了 Meldrum 酸与硝基烯烃的不对称迈克尔加成。硫脲催化剂的功能性也通过制备和测试众所周知的双-(3,5-三氟甲基)苯基取代催化剂的硫脲-N-甲基化类似物来探查。
• Recyclable C2-symmetric tertiary amine-squaramide organocatalysts: Design and application to asymmetric synthesis of γ-nitrocarbonyl compounds
  作者：Alexey A. Kostenko、Alexander S. Kucherenko、Sergei G. Zlotin

  DOI：10.1016/j.tet.2018.07.043

  日期：2018.9

  hane spacer group have been synthesized. Among them, amine 8b with a different configuration of stereocenters in 1,2-di(pyridin-2-yl)ethane and 1,2-diaminocyclohexane units efficiently catalyzed asymmetric additions of β-dicarbonyl compounds to nitroolefins and domino reaction of ortho-(tosylamino)chalcone with β-nitrostyrene in wet (20 equiv. of H2O) DCM, affording corresponding adducts in up to 99%

  合成了带有方酰胺片段和1，2-二（吡啶-2-基）乙烷间隔基的简单的C 2对称手性叔胺。其中，在1,2-二（吡啶-2-基）乙烷和1,2-二氨基环己烷单元中具有不同立体中心构型的胺8b有效地催化了β-二羰基化合物向硝基烯烃的不对称加成反应以及邻位-（甲苯磺酰查尔酮与β-硝基苯乙烯的湿（20当量H 2 O）DCM中，以高达99％的收率和94％ee的产率提供相应的加合物。开发的过程是可扩展的。由于在有机溶剂和水中的不良溶解性，催化剂可以容易地从反应混合物中分离出来，并且可以在反应中再使用10次以上，而不会损害对映体的富集度和产物的收率。
• A new multicomponent reaction for direct synthesis of primary γ-nitroamides
  作者：Caroline R. Montes D'Oca、Jessica C. da Silva、Esthefani P. Guedes、Marcelo G. Montes D'Oca、Leonardo S. Santos、Fabiane M. Nachtigall、Dennis Russowsky

  DOI：10.1039/c6ra22141f

  日期：——

  A new multicomponent reaction for direct synthesis of [gamma]-nitroamides promoted by ammonium carbonate was developed. A series of [gamma]-nitroamides were synthesized in 35-93% yield from Meldrum's acid, aromatic or aliphatic...

  开发了一种新的由碳酸铵促进的直接合成γ-硝基酰胺的多组分反应。由Meldrum的酸，芳族或脂族化合物合成了一系列γ-硝基酰胺，产率为35-93％。
• Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes
  作者：James C. Anderson、Andreas S. Kalogirou、Graham J. Tizzard

  DOI：10.1016/j.tet.2014.10.042

  日期：2014.12

  The conjugate addition nitro-Mannich reactions of ethyl-beta-nitroacrylate (1) and beta-nitrostyrene (2) with electron rich aromatic nucleophiles, stabilized carbanions, alcohols, amines, thiols, and diphenyl phosphine oxide were investigated. The one pot conjugate addition nitro-Mannich reaction was unsuccessful except for the addition of alkoxides to 2 in alcohol as solvent. Isolation of the conjugate addition products followed by deprotonation with (BuLi)-Bu-n and treatment with a simple imine in the presence of TFA led to beta-nitroamine derived products. Products derived from 1 spontaneously cyclised in only a few examples and on the whole led to inherently unstable products. Products derived from 2 were isolated as their trifluoroacetamides, gave good yields of single diastereoisomers for aromatic and alkoxide nucleophiles and the structures were verified by single crystal X-ray crystallography. Products derived from amine nucleophiles were isolated in low yields while sulfur nucleophiles gave poor diastereoselectivities. (C) 2014 Elsevier Ltd. All rights reserved.
• Li, Jing-Hua; Li, Zu-Guang; Chen, Qing-Guang, Journal of Chemical Research, 2004, # 11, p. 758 - 759
  作者：Li, Jing-Hua、Li, Zu-Guang、Chen, Qing-Guang

  DOI：——

  日期：——