4-nitro-1-(3-methylphenyl)-3-phenylbutane-1-one | 1613141-90-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-nitro-1-(3-methylphenyl)-3-phenylbutane-1-one
• 英文别名: 4-nitro-3-phenyl-1-(m-tolyl)butan-1-one；1-(3-Methylphenyl)-4-nitro-3-phenylbutan-1-one；1-(3-methylphenyl)-4-nitro-3-phenylbutan-1-one
• CAS: 1613141-90-4
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: QQCSORDMUJZUDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-nitro-1-(3-methylphenyl)-3-phenylbutane-1-one 在 Ni-doped silica 、 氢气 作用下， 以 乙腈 为溶剂， 120.0 ℃ 、2.0 MPa 条件下， 反应 20.0h， 以85%的产率得到3-phenyl-5-(m-tolyl)-3,4-dihydro-2H-pyrrole
  参考文献：
  名称：

  酮、醛和硝基烷烃加氢环化合成 3,4-二氢-2H-吡咯

  摘要：

  一种高活性、选择性和可重复使用的镍催化剂已被开发并用于通过硝基酮的氢化和随后的环化合成 3,4-二氢-2 H-吡咯。该催化剂是从 24 种非均相催化剂的库中鉴定出来的。我们的氢化/环化反应的关键是醛和酮作为官能团的耐受性以及高效氢化脂肪族硝基化合物的能力。

  DOI：

  10.1002/chem.202201307
• 作为产物：
  描述：

  反式硝基苯乙烯 、 3'-甲基苯乙酮 在 藜芦酸 、 (1R,2R)-反式-N-Boc-1,2-二氨基环己烷 、 (1S,2S)-BOC-1,2-环己二胺 作用下， 以 氯仿 为溶剂， 生成 4-nitro-1-(3-methylphenyl)-3-phenylbutane-1-one
  参考文献：
  名称：

  Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines

  摘要：

  Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched beta-substituted gamma-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.07.011

文献信息

• Synthesis of multisubstituted 1H-pyrrole: selenium-catalyzed reaction of γ-nitro substituted carbonyl compounds and carbon monoxide
  作者：Rui Umeda、Tsukasa Mashino、Yutaka Nishiyama

  DOI：10.1016/j.tet.2014.04.061

  日期：2014.7

  The novel and efficient selenium-catalyzed reductive N-heterocyclization of γ-nitro substituted carbonyl compounds with carbon monoxide has been developed. Various multisubstituted 1H-pyrroles can be easily prepared by this protocol. The one-pot synthesis of ethyl 1H-pyrrole-3-carboxylate derivatives was also successfully attained by the selenium-catalyzed reaction of β-ketoester, vinyl nitro compounds and

  已经开发出新颖和有效的硒催化一氧化碳对γ-硝基取代的羰基化合物进行硒催化的还原性N-杂环化。通过该方案可以容易地制备各种多取代的1 H-吡咯。通过硒催化β-酮酸酯，乙烯基硝基化合物和一氧化碳的反应，也成功地完成了1 H-吡咯-3-羧酸乙酯衍生物的一锅法合成。
• Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines
  作者：Jesús Flores-Ferrándiz、Alexander Stiven、Lia Sotorríos、Enrique Gómez-Bengoa、Rafael Chinchilla

  DOI：10.1016/j.tetasy.2015.07.011

  日期：2015.9

  Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched beta-substituted gamma-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of 3,4‐Dihydro‐2 <i>H</i> ‐Pyrroles from Ketones, Aldehydes, and Nitro Alkanes via Hydrogenative Cyclization
  作者：Barbara Klausfelder、Patricia Blach、Niels de Jonge、Rhett Kempe

  DOI：10.1002/chem.202201307

  日期：2022.8.22

  developed and employed for the synthesis of 3,4-dihydro-2H-pyrroles via hydrogenation and subsequent cyclization of nitro ketones. The catalyst was identified from a library of 24 heterogeneous catalysts. The key to our hydrogenation/cyclization reaction is the tolerance of aldehydes and ketones as functional groups and the ability to hydrogenate aliphatic nitro compounds efficiently.

  一种高活性、选择性和可重复使用的镍催化剂已被开发并用于通过硝基酮的氢化和随后的环化合成 3,4-二氢-2 H-吡咯。该催化剂是从 24 种非均相催化剂的库中鉴定出来的。我们的氢化/环化反应的关键是醛和酮作为官能团的耐受性以及高效氢化脂肪族硝基化合物的能力。