4'-methoxy-2-nitropropiophenone | 65662-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-methoxy-2-nitropropiophenone
• 英文别名: 2-nitro-1-(4-methoxyphenyl)propanone；1-(4-Methoxyphenyl)-2-nitropropan-1-one
• CAS: 65662-59-1
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: NJSOYRHNACEULJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-methoxy-2-nitropropiophenone 在 1-苯甲基-1,4-二氢烟酰胺 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 48.0h， 以52%的产率得到对甲氧基苯丙酮
  参考文献：
  名称：

  1-Benzyl-1,4-dihydronicotinamide as a reagent for replacing aliphatic nitro groups by hydrogen. An electron-transfer chain reaction

  摘要：

  DOI：

  10.1021/ja00350a045
• 作为产物：
  描述：

  2-nitro-1-hydroxy-1-(4-methoxy-phenyl)-propane 在 sodium dichromate 、 硫酸 作用下， 以 水 为溶剂， 生成 4'-methoxy-2-nitropropiophenone
  参考文献：
  名称：

  1-Benzyl-1,4-dihydronicotinamide as a reagent for replacing aliphatic nitro groups by hydrogen. An electron-transfer chain reaction

  摘要：

  DOI：

  10.1021/ja00350a045

文献信息

• General Allylic C–H Alkylation with Tertiary Nucleophiles
  作者：Jennifer M. Howell、Wei Liu、Andrew J. Young、M. Christina White

  DOI：10.1021/ja500726e

  日期：2014.4.16

  A general method for intermolecular allylic C–H alkylation of terminal olefins with tertiary nucleophiles has been accomplished employing palladium(II)/bis(sulfoxide) catalysis. Allylic C–H alkylation furnishes products in good yields (avg. 64%) with excellent regio- and stereoselectivity (>20:1 linear:branched, >20:1 E:Z). For the first time, the olefin scope encompasses unactivated aliphatic olefins

  已经使用钯（II）/双（亚砜）催化完成了末端烯烃与叔亲核试剂的分子间烯丙基 C-H 烷基化的通用方法。烯丙基 C–H 烷基化以良好的收率（平均 64%）提供具有出色区域和立体选择性（>20:1 线性：支化，>20:1 E:Z）的产品。烯烃范围首次涵盖未活化的脂肪族烯烃以及活化的芳族/杂芳族烯烃和 1,4-二烯。将烯丙基部分附加到复杂支架上的便利性被利用来实现这种温和且选择性的烯丙基 C–H 烷基化，从而使酚类天然产物快速多样化。叔亲核试剂范围很广，包括用于进一步加工的潜在功能（例如，脂肪醇、α,β-不饱和酯）。
• Nitrosocarbonyl–Henry and Denitration Cascade: Synthesis of α-Ketoamides and α-Keto Oximes
  作者：Mallu Kesava Reddy、Sumitava Mallik、Isai Ramakrishna、Mahiuddin Baidya

  DOI：10.1021/acs.orglett.7b00482

  日期：2017.4.7

  Henry reaction of in situ generated nitrosocarbonyl intermediates and concomitant denitration cascade has been developed. The reaction is catalyzed by organic base at room temperature offering α-ketoamides, a demanding scaffold for drug discovery, in high yields. An alteration of substitution pattern also produced α-keto oximes, a high-value synthon. The protocol features operational simplicity and broad

  原位生成的亚硝基羰基中间体和随之而来的反硝化级联反应已实现了前所未有的亨利反应。该反应在室温下被有机碱催化，以高收率提供了α-酮酰胺，这是药物发现所必需的支架。取代模式的改变也产生了α-酮肟，一种高价值的合成子。该协议具有操作简便和广泛的基材范围的特点。
• A high performance oxidation method for secondary alcohols by inductive activation of TEMPO in combination with pyridine–bromine complexes
  作者：Zhen-Wu Mei、Takumi Omote、Mounir Mansour、Hiroyuki Kawafuchi、Yutaka Takaguchi、Anny Jutand、Sadao Tsuboi、Tsutomu Inokuchi

  DOI：10.1016/j.tet.2008.08.051

  日期：2008.11

  A new TEMPO-mediated catalytic oxidation method in combination with Py center dot HBr3 (stoichiometric) is developed for oxidation of secondary alcohols to the corresponding ketones. The performance of this oxidizing system is better compared with that of TEMPO method combined with R4NBr3 center dot Poly(4-vinylpyridine) HBr3 can be used in place of Py center dot HBr3. The electron-withdrawing substituent at the C-4 position of TEMPO increases the reactivity of TEMPO significantly in the oxidation of electron-deficient alcohols Such as polyhaloalkylmethanols. Inductive effect of the substituent of TEMPO is discussed through the characterization of the redox potential of N-O radical by cyclic voltammetry. (C) 2008 Elsevier Ltd. All rights reserved.
• Ratsino,E.V. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 2320 - 2322
  作者：Ratsino,E.V. et al.

  DOI：——

  日期：——
• Tyrkov, A. G.; Ladyzhnikova, T. D.; Altukhov, K. V., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 5.2, p. 977
  作者：Tyrkov, A. G.、Ladyzhnikova, T. D.、Altukhov, K. V.

  DOI：——

  日期：——