2-(1-nitroethyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-nitroethyl)naphthalene
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: FJDBSDWGEBXXAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2-(1-nitroethyl)naphthalene 在 溶剂黄146 、 sodium nitrite 作用下， 以 甲基叔丁基醚 为溶剂， 反应 24.0h， 以44.2 mg的产率得到2-萘乙酮
  参考文献：
  名称：

  通过钯催化苯酚衍生物与硝基烷烃的交叉偶联以及随后的 Nef 反应获得酮

  摘要：

  芳基酮是由芳基三氟甲磺酸酯和硝基烷烃通过钯催化的交叉偶联然后在一锅合成中的 Nef 型反应制备的。

  DOI：

  10.1002/ejoc.202200731
• 作为产物：
  描述：

  硝基乙烷 、 2-溴萘 在 tris(dibenzylideneacetone)dipalladium (0) caesium carbonate 、 2-二-叔丁基磷-2'-甲基联苯 作用下， 以 乙二醇二甲醚 为溶剂， 以96%的产率得到2-(1-nitroethyl)naphthalene
  参考文献：
  名称：

  Palladium-Catalyzed Monoarylation of Nitroalkanes

  摘要：

  A general protocol for the Pd-catalyzed-arylation of nitroalkanes is described. Substituted aryl bromides as well as aryl chlorides can be coupled efficiently with a variety of nitroalkanes under mild conditions to selectively yield the monoarylated products. This method tolerates a number of functional groups including ketones, esters, and olefins. Notably, the arylation of nitroalkanes can be effected chemoselectively over ketone and ester arylation.

  DOI：

  10.1021/jo010953v

文献信息

• An asymmetric sp3–sp3 cross-electrophile coupling using ‘ene’-reductases
  作者：Haigen Fu、Jingzhe Cao、Tianzhang Qiao、Yuyin Qi、Simon J. Charnock、Samuel Garfinkle、Todd K. Hyster

  DOI：10.1038/s41586-022-05167-1

  日期：2022.10.13

  XEC between alkyl halides and nitroalkanes catalyzed by flavin-dependent ‘ene’-reductases. Photoexcitation of the enzyme-templated charge-transfer complex between an alkyl halide and flavin cofactor enables the chemoselective reduction of alkyl halide over the thermodynamically favored nitroalkane partner. The key C–C bond-forming step occurs via the reaction of an alkyl radical with an in situ generated

  C sp 3 –C sp 3键的催化不对称构建仍然是有机合成中最重要的挑战之一。1金属催化的交叉亲电子偶联 (XEC) 已成为形成 C-C 键的强大工具。2-5然而，耦合两种不同的具有高交叉选择性和立体选择性的 C sp 3 -亲电子试剂仍然是一个未解决的挑战。在这里，我们报道了由黄素依赖性“烯”还原酶催化的卤代烷和硝基烷之间的高度化学和对映选择性C sp 3 –C sp 3 XEC。卤代烷和黄素辅助因子之间的酶模板电荷转移复合物的光激发使得卤代烷相对于热力学有利的硝基烷伙伴物发生化学选择性还原。关键的 C-C 键形成步骤是通过烷基自由基与原位生成的硝基发生反应，形成硝基阴离子，然后硝基阴离子分解形成亚硝酸根和烷基。酶控制的氢原子转移提供了高水平的对映选择性。这种反应性在小分子催化中是未知的，凸显了酶利用新机制来解决长期存在的合成挑战的潜力。
• Palladium-Catalyzed Monoarylation of Nitroalkanes
  作者：Erasmus M. Vogl、Stephen L. Buchwald

  DOI：10.1021/jo010953v

  日期：2002.1.1

  A general protocol for the Pd-catalyzed-arylation of nitroalkanes is described. Substituted aryl bromides as well as aryl chlorides can be coupled efficiently with a variety of nitroalkanes under mild conditions to selectively yield the monoarylated products. This method tolerates a number of functional groups including ketones, esters, and olefins. Notably, the arylation of nitroalkanes can be effected chemoselectively over ketone and ester arylation.
• Synthesis of 5-alkyl-5-aryl-γ-lactams from 1-aryl-substituted nitroalkanes and methyl acrylate via Michael addition and reductive lactamization
  作者：Jingjing Xu、Xingyao Li、Jinlong Wu、Wei-Min Dai

  DOI：10.1016/j.tet.2014.04.074

  日期：2014.6

  A general method for accessing 5-alkyl-5-aryl-gamma-lactams has been developed using readily available aryl bromides, nitroalkanes, and methyl acrylate as the starting materials. The palladium-catalyzed arylation of nitroalkanes gave the 1-aryl-substituted nitroalkanes, which underwent the DBU-mediated Michael addition with methyl acrylate at room temperature to afford the methyl 4-aryl-4-nitroalkanoates. The latter were then subjected to the nitro reduction using NaBH4-NiCl2 center dot 6H(2)O in MeOH at 0 degrees C to furnish, after treatment with aqueous K2CO3 at room temperature, the 5-alkyl-5-aryl-gamma-lactams in good to excellent overall yields. Selected examples of N-alkylation of the gamma-lactams were also illustrated. (C) 2014 Elsevier Ltd. All rights reserved.
• Access to Ketones through Palladium‐Catalyzed Cross‐Coupling of Phenol Derivatives with Nitroalkanes Followed by Nef Reaction
  作者：Xiaoyu He、Sengui Hu、Yuxuan Xiao、Lin Yu、Wengui Duan

  DOI：10.1002/ejoc.202200731

  日期：2022.9.20

  Aryl ketones were prepared from aryl triflates and nitroalkanes through a palladium-catalyzed cross-coupling followed by Nef-type reaction in a one-pot synthesis.

  芳基酮是由芳基三氟甲磺酸酯和硝基烷烃通过钯催化的交叉偶联然后在一锅合成中的 Nef 型反应制备的。