3-硝基丙-1-烯-2-基苯 | 58502-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-硝基丙-1-烯-2-基苯
• 英文名称: (3-nitroprop-1-en-2-yl)benzene
• 英文别名: 3-nitroprop-1-en-2-ylbenzene
• CAS: 58502-68-4
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: GBXJALJUIQYMCT-UHFFFAOYSA-N

物化性质

• 沸点：
  292.2±19.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-硝基丙-1-烯-2-基苯 在 葡萄糖 、 bakers' yeast 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以80%的产率得到(+)-(R)-1-nitro-2-phenylpropane
  参考文献：
  名称：

  Asymmetric reduction of nitro olefins by fermenting bakers' yeast

  摘要：

  DOI：

  10.1021/jo00269a011
• 作为产物：
  描述：

  苯,(2-硝基-1-丙烯基)-,(E)- 在 甲酸 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 三乙胺 、 (1R,2R)-(-)-N-(对甲基苯磺酰基)-1,2-二苯基乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-硝基丙-1-烯-2-基苯
  参考文献：
  名称：

  Chemoselective and enantioselective transfer hydrogenation of β,β-disubstituted nitroalkenes catalyzed by a water-insoluble chiral diamine–rhodium complex in water

  摘要：

  Asymmetric transfer hydrogenation of beta,beta-disubstituted nitroalkenes catalyzed by a chiral diamine-rhodium complex in combination with HCO(2)Na-HCO(2)H as a hydrogen source in water was successfully realized with high reactivity, excellent chemoselectivity and good enantioselectivity. The metal precursor and pH value of the aqueous solution have a large influence on the reactivity and chemoselectivity. The substituents on the benzene rings and the sulfonyl groups of TsDPEN have significant effects on the enantioselectivity. This catalytic asymmetric transformation is one of the most practical pathways to obtain optically active nitroalkanes. (C) 2010 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tetasy.2010.05.046

文献信息

• Highly Enantioselective Hydrogenation of β,β‐Disubstituted Nitroalkenes
  作者：Shengkun Li、Kexuan Huang、Bonan Cao、Jiwen Zhang、Wenjun Wu、Xumu Zhang

  DOI：10.1002/anie.201202715

  日期：2012.8.20

  Building the building blocks: A highly enantioselective hydrogenation of β‐aryl‐β‐alkyl disubstituted nitroalkenes 1 has been developed. This method results in enantiomerically pure nitroalkanes 2, which are versatile precursors for chemical synthesis.

  构建基石：已开发出β-芳基-β-烷基二取代硝基烯烃1的高度对映选择性氢化。该方法产生对映体纯的硝基烷2，其是用于化学合成的通用前体。
• Controllable Activation of β-Alkyl Nitroalkenes: Regioselective Synthesis of Allyl and Vinyl Sulfones
  作者：Ye Wang、Guowei Xiong、Chuanxin Zhang、Yunfeng Chen

  DOI：10.1021/acs.joc.0c02869

  日期：2021.3.5

  hydrazides depended to a great extent on the choice of a solvent and catalyst. In the presence of dimethylformamide (DMF), β-alkyl nitroalkenes more likely converted into electron-rich allyl nitro compounds, which reacted with sulfonyl hydrazides to afford allyl sulfones with high regioselectivity. While in acetonitrile (CH3CN), vinyl sulfones were obtained directly via sulfonation of electron-deficient β-alkyl

  β-烷基硝基烯烃与磺酰肼的区域特异性自由基反应在很大程度上取决于溶剂和催化剂的选择。在二甲基甲酰胺（DMF）的存在下，β-烷基硝基烯烃更可能转化为富含电子的烯丙基硝基化合物，该化合物与磺酰肼反应生成具有高区域选择性的烯丙基砜。在乙腈（CH 3 CN）中时，可通过缺电子的β-烷基硝基烯烃的磺化反应直接获得乙烯基砜。机理研究表明，区域选择性受β-烷基硝基烯烃和烯丙基硝基化合物平衡的控制。
• Allylic C–S Bond Construction through Metal-Free Direct Nitroalkene Sulfonation
  作者：Xue Lei、Lei Zheng、Chuanxin Zhang、Xiaodong Shi、Yunfeng Chen

  DOI：10.1021/acs.joc.7b02595

  日期：2018.2.16

  protocol was developed for the preparation of allylic sulfones through direct condensation of sodium arylsulfinates and β,β-disubstituted nitroalkenes. The key step of this process was the Lewis base-promoted equilibrium between nitroalkenes and allylic nitro compounds. Through this process, the readily available conjugated nitroalkenes can be easily converted into allylic nitro compounds, which contain

  开发了一种无金属的开放烧瓶规程，用于通过芳基亚磺酸钠和β，β-二取代的硝基烯烃的直接缩合制备烯丙基砜。该过程的关键步骤是硝基烯烃与烯丙基硝基化合物之间的路易斯碱促进的平衡。通过该方法，容易获得的共轭硝基烯烃可以容易地转化为烯丙基硝基化合物，其对磺酰基自由基加成包含更多的反应性C═C键。结果，在温和条件下以优异的产率制备了烯丙基砜，具有广泛的底物范围。
• Enantioselective iridium-catalyzed hydrogenation of β,β-disubstituted nitroalkenes
  作者：Yan-Bo Yu、Lei Cheng、Yi-Pan Li、Yue Fu、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1039/c6cc01273f

  日期：——

  An iridium complex with a newly prepared chiral spiro amino-phosphine ligand efficiently catalyzed the hydrogenation of both [small beta]-aryl-[small beta]-methyl-nitroalkenes and [small beta]-alkyl-[small beta]-methyl-nitroalkenes to the corresponding saturated nitroalkanes, which represents the first report...

  具有新制备的手性螺氨基氨基膦配体的铱络合物有效地催化了β-芳基-β-甲基-硝基硝基和β-烷基-β-甲基-硝基硝基的小氢化。到相应的饱和硝基烷烃，这是第一个报告。
• Transition Metal-Free Oxidative Cross-Coupling Reaction of Activated Olefins with <i>N</i>-Alkyl Amides
  作者：Miaomiao Li、Lei Zheng、Li Ma、Yunfeng Chen

  DOI：10.1021/acs.joc.0c02837

  日期：2021.3.5

  The K2S2O8-mediated transition metal-free oxidative cross-coupling reaction of activated olefins with N-alkyl amides was developed, and the reaction gave N-allylic amides in moderate to good yield. This reaction protocol was suitable for different kinds of activated olefins.

  进行了K 2 S 2 O 8介导的活化烯烃与N-烷基酰胺的无过渡金属氧化交叉偶联反应，该反应以中等至良好的收率得到了N-烯丙基酰胺。该反应方案适用于不同种类的活化烯烃。