1-(1,3-dinitropropan-2-yl)-4-methoxybenzene | 117538-86-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(1,3-dinitropropan-2-yl)-4-methoxybenzene
• 英文别名: 1,3-dinitro-2(4-methoxyphenyl)propane；1-(1,3-Dinitropropan-2-yl)-4-methoxybenzene
• CAS: 117538-86-0
• 化学式: C₁₀H₁₂N₂O₅
• 分子量: 240.216
• InChiKey: VPXGMVYAYXJBDE-UHFFFAOYSA-N

物化性质

• 沸点：
  410.7±45.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(1,3-dinitropropan-2-yl)-4-methoxybenzene 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 9.5h， 生成 1-[(4-Chlorophenyl)methyl]-4-(4-methoxyphenyl)-2-methyl-3-nitrobenzene
  参考文献：
  名称：

  Synthesis of poly-substituted nitrobenzene derivatives from Baylis–Hillman adducts via [3+3] annulation protocol

  摘要：

  Poly-substituted nitrobenzenes were synthesized from Baylis-Hillman adducts via the [3+3] annulation strategy as the key step. 1,3-Dinitroalkanes served as the 1,3-dinucleophilic component and the Baylis-Hillman acetates as a 1,3-dielectrophilic part. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.146
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 在 盐酸 、 乙二胺 作用下， 以 水 、 甲苯 为溶剂， 反应 18.03h， 生成 1-(4-甲氧苯基)-2-硝基乙烯 、 1-(1,3-dinitropropan-2-yl)-4-methoxybenzene
  参考文献：
  名称：

  Compartmentalization of Incompatible Reagents within Pickering Emulsion Droplets for One-Pot Cascade Reactions

  摘要：

  It is a dream that future synthetic chemistry can mimic living systems to process multistep cascade reactions in a one-pot fashion. One of the key challenges is the mutual destruction of incompatible or opposing reagents, for example, acid and base, oxidants and reductants. A conceptually novel strategy is developed here to address this challenge. This strategy is based on a layered Pickering emulsion system, which is obtained through lamination of Pickering emulsions. In this working Pickering emulsion, the dispersed phase can separately compartmentalize the incompatible reagents to avoid their mutual destruction, while the continuous phase allows other reagent molecules to diffuse freely to access the compartmentalized reagents for chemical reactions. The compartmentalization effects and molecular transport ability of the Pickering emulsion were investigated. The deacetalization-reduction, deacetalization-Knoevenagel, deacetalization-Henry and diazotization-iodization cascade reactions demonstrate well the versatility and flexibility of our strategy in processing the one-pot cascade reactions involving mutually destructive reagents.

  DOI：

  10.1021/ja512337z

文献信息

• Base-catalyzed reactions enhanced by solid acids: Amine-catalyzed nitroaldol (Henry) reactions enhanced by silica gel or mesoporous silica SBA-15
  作者：Kiyoshi Tanemura、Tsuneo Suzuki

  DOI：10.1016/j.tetlet.2017.12.050

  日期：2018.1

  The reactions of various aldehydes with CH3NO2 catalyzed by Et3N, n-C6H13NH2, and Me2N(CH2)2NH2 were accelerated by the addition of silica gel to give aromatic (aliphatic) β-nitroalcohols, aromatic nitroalkenes, and aromatic 1,3-dinitroalkanes, respectively. Mesoporous silica SBA-15 showed higher activity than silica gel for the synthesis of aromatic nitroalkenes by the reactions of the corresponding

  各种醛的用CH反应3 NO 2通过催化的Et 3 N，Ñ -C 6 ħ 13 NH 2，和Me 2 N（CH 2）2 NH 2通过加入加速硅胶，得到芳族（脂族）分别是β-硝基醇，芳族硝基烯烃和芳族1,3-二硝基烷烃。通过相应的醛与n -C 6 H催化的CH 3 NO 2的反应，介孔二氧化硅SBA-15在合成芳族硝基烯烃方面表现出比硅胶更高的活性。13 NH 2。
• Highly Efficient C−C Bond-Forming Reactions in Aqueous Media Catalyzed by Monomeric Vanadate Species in an Apatite Framework
  作者：Takayoshi Hara、Satoko Kanai、Kohsuke Mori、Tomoo Mizugaki、Kohki Ebitani、Koichiro Jitsukawa、Kiyotomi Kaneda

  DOI：10.1021/jo0614745

  日期：2006.9.1

  reactions such as Michael and aldol reactions in aqueous media and the H−D exchange reactions using deuterium oxide. For example, a 200-mmol-scale Michael reaction under triphasic conditions proceeded rapidly, with an extremely high turnover number of up to 260 400 and an excellent turnover frequency of 48 s-1. No vanadium leaching was detected during the above reactions, and the catalyst was readily recycled

  甲钒酸钙磷灰石（VAP），其中PO 4 3 -羟基磷灰石（HAP），钙10（PO 4）6（OH）2，完全被取代的VO 4 3 -在磷灰石框架，被合成。VAp的理化分析表明存在分离出的VO 4具有五价氧化态的四面体单元。VAp可作为高性能异质碱催化剂，用于各种碳-碳键形成反应，例如水性介质中的迈克尔和醛醇反应以及使用氘化氢的H-D交换反应。例如，三相条件下的200毫摩尔规模迈克尔反应快速进行，具有高达260 400的非常高的转换数和第48号第一个极好的转换频率- 1。在上述反应过程中未检测到钒的浸出，并且催化剂易于循环使用而没有活性损失。
• Ethylenediamine-functionalized magnetic Fe₃O₄@SiO₂ nanoparticles: cooperative trifunctional catalysis for selective synthesis of nitroalkenes
  作者：Fengjun Xue、Yahao Dong、Peibo Hu、Yanan Deng、Yuping Wei

  DOI：10.1039/c5ra11798d

  日期：——

  The designed nanocatalyst Fe₃O₄@SiO₂–NH₂ was highly active for selective synthesis of nitroalkenes through cooperative trifunctional catalysis of primary amine, secondary amine and Si–OH groups.

  设计的纳米催化剂 Fe₃O₄@SiO₂–NH₂ 对通过初级胺、次级胺和 Si–OH 基团的协同三功能催化选择性合成硝基烯烃具有很高的活性。
• Co‐Polymeric Nanosponges from Cellulose Biomass as Heterogeneous Catalysts for amine‐catalyzed Organic Reactions
  作者：Laura Riva、Carlo Punta、Alessandro Sacchetti

  DOI：10.1002/cctc.202001157

  日期：2020.12.16

  nano‐porous system guarantees a complete penetration of CNS, allowing reagents to diffuse within. Indeed, by modulating reaction conditions (catalyst loading, temperature, solvent, microwave versus conventional heating, relative ratio of reagents) it was possible to drive selectivity towards the desired products, while maintaining high efficiency in terms of conversion. The catalyst could be re‐used several

  由生物质废物源制备的非均相催化剂引起了越来越多的兴趣。原因在于将循环经济的良性方法与非均相催化的综合优势相结合的可能性，即系统的循环利用和提高对所需产物的选择性的可能性。本文中，我们报道了一种高度多孔的纤维素纳米海绵（CNS）及其作为亨利和Knoevenagel反应（两种经典的氨基催化转化）的可回收催化剂的用途。该材料是通过在柠檬酸存在下，TEMPO氧化纤维素纳米纤维（TOCNF）与25 kDa的支链聚乙烯亚胺（bPEI）交联而获得的。已开发出CNS作为用于水修复的吸附剂材料，但是从未研究过将其用作非均相催化剂。充分表征的微孔和纳米孔系统可确保CNS完全渗透，从而使试剂能够在其中扩散。实际上，通过调节反应条件（催化剂负载，温度，溶剂，微波与常规加热（试剂的相对比率）相比，有可能将选择性推向所需产物，同时保持高转化率。该催化剂可以重复使用几次，而不会降低催化效率。在大多数情况下，产品的分布与
• Michael addition at neutral pH: a facile synthesis of 1,3-dinitroalkanes
  作者：Porag Bora、Pranjal P. Bora、Barisha Wahlang、Ghanashyam Bez

  DOI：10.1139/cjc-2017-0257

  日期：2017.12

  Base-catalyzed Michael addition of nitroalkane to conjugated nitroalkene suffers serious practical difficulties due to the formation of oligomeric byproduct. Given its importance for synthesis of pharmacologically relevant organic compounds, a scalable synthesis of 1,3-dinitroalkane is developed by addition of nitroalkane to nitroalkene in aqueous phosphate buffer at pH 7.0 with no added traditional base catalyst.

  碱催化的硝基烷基对共轭硝基烯烃的Michael加成受到严重的实际困难的影响，因为会形成寡聚物副产物。鉴于它对合成药理学相关有机化合物的重要性，通过在pH 7.0的水相磷酸盐缓冲液中将硝基烷基加到硝基烯烃中，开发了一种可扩展的1,3-二硝基烷基合成方法，无需添加传统的碱催化剂。