2-(1,3-dinitropropan-2-yl)naphthalene | 266685-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1,3-dinitropropan-2-yl)naphthalene
• CAS: 266685-21-6
• 化学式: C₁₃H₁₂N₂O₄
• 分子量: 260.249
• InChiKey: FXLHANFAOQFFBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1,3-dinitropropan-2-yl)naphthalene 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 9.0h， 生成 2-[(4E)-4-benzylidene-3-methyl-2,6-dinitrocyclohex-2-en-1-yl]naphthalene
  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：

  硝基甲烷 、 2-萘甲醛 在 silica gel 、 N,N-二甲基乙二胺 作用下， 反应 4.0h， 以75%的产率得到2-(1,3-dinitropropan-2-yl)naphthalene
  参考文献：
  名称：

  固体酸增强的碱催化反应：硅胶或中孔二氧化硅SBA-15增强的胺催化硝基醛（Henry）反应

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2017.12.050

文献信息

• Diastereoselective, One-Pot Synthesis of Polyfunctionalized Bicyclo[3.3.1]nonanes by an Anionic Domino Process
  作者：Luciano Barboni、Serena Gabrielli、Alessandro Palmieri、Cristina Femoni、Roberto Ballini

  DOI：10.1002/chem.200900366

  日期：2009.8.10

  One pot, many reactions! The reaction of two equivalents of ethyl(2‐bromomethyl)acrylate with dinitroalkanes (see scheme) leads to the one‐pot, diastereoselective synthesis of a variety of polyfunctionalized bicyclo[3.3.1]nonanes in very good overall yields. The reaction proceeds through an anionic domino process, with the in situ generation of four new CC bonds.

  一锅多反应！两当量的（2-溴甲基）丙烯酸乙酯与二硝基烷烃的反应（见方案）导致以非常好的总产率单锅、非对映选择性合成各种多官能化双环[3.3.1]壬烷。该反应通过阴离子多米诺骨牌过程进行，原位生成四个新的 C  C 键。
• Protein-Mediated Nitroaldol Addition in Aqueous Media. Catalytic Promiscuity or Unspecific Catalysis?
  作者：Eduardo Busto、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1021/op100130c

  日期：2011.1.21

  A high efficient and environmentally friendly procedure for the production of aromatic and heteroaromatic beta-nitroalcohols has been developed. This synthetic approach involves the condensation of an appropriate aldehyde with 1-nitroalkanes in aqueous media using as catalyst the inexpensive carrier protein Bovine serum albumin (BSA). According to the experimental data, the Henry reaction between aromatic aldehydes and nitroalkanes in aqueous media proceeds by unspecific protein catalysis rather than catalytic promiscuity. By proper choice of the reaction conditions, the corresponding nitroalcohols were obtained in yields up to 91% at 30 degrees C. Catalyst recycling and scale-up of the reactions have been considered as important factors, in order to show this methodology as a valuable synthetic approach.
• How to Make Five Contiguous Stereocenters in One Reaction: Asymmetric Organocatalytic Synthesis of Pentasubstituted Cyclohexanes
  作者：Efraím Reyes、Hao Jiang、Andrea Milelli、Petteri Elsner、Rita G. Hazell、Karl Anker Jørgensen

  DOI：10.1002/anie.200704454

  日期：2007.12.10
• Cooperative Catalysis of Primary and Tertiary Amines Immobilized on Oxide Surfaces for One‐Pot CC Bond Forming Reactions
  作者：Ken Motokura、Mizuki Tada、Yasuhiro Iwasawa

  DOI：10.1002/anie.200802515

  日期：2008.11.17
• 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。