1-methoxy-4-(1-nitromethyl-propyl)-benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methoxy-4-(1-nitromethyl-propyl)-benzene
• 英文别名: 1-methoxy-4-[1-(nitromethyl)propyl]benzene；1-methoxy-4-(1-nitrobutan-2-yl)benzene；rac-2-(4-methoxyphenyl)-nitrobutane
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: UNJGHQRKPADTMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四甲基乙二胺 、 1-methoxy-4-(1-nitromethyl-propyl)-benzene 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 氧气 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以85%的产率得到3-(4-methoxyphenyl)-N,N-dimethyl-2-nitropentan-1-amine
  参考文献：
  名称：

  可见光促进的C ？C键裂解：离子和氨基自由基的光催化生成

  摘要：

  Photoscissors：在结构上可变和合成健壮亚胺离子和氨基的基团的物种可以通过C的可见光促进photoredox裂解同时生成在简单邻二胺前体C键非常温和的反应条件下进行。

  DOI：

  10.1002/anie.201202880
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 4.67h， 生成 1-methoxy-4-(1-nitromethyl-propyl)-benzene
  参考文献：
  名称：

  可见光光氧化还原催化还原硝基化合物制肟的新方法

  摘要：

  在可见光辐射，Ru（bpy）3 Cl 2光催化剂，Hünig碱，Mg（ClO 4）2活化和MeCN溶剂的协同作用下，一系列硝基化合物被平滑还原为相应的肟。当采用经典贝克曼重排进行编排时，这种非常温和且对环境无害的方案使得从简单的前体硝基环己烷中即可轻松获得诸如己内酰胺之类的高价值工业原料。

  DOI：

  10.1021/ol4009443

文献信息

• One-pot multi-substrate enantioselective conjugate addition of diethylzinc to nitroalkenes
  作者：Ate Duursma、Adriaan J Minnaard、Ben L Feringa

  DOI：10.1016/s0040-4020(02)00574-4

  日期：2002.7

  catalyzed enantioselective conjugate addition of diethylzinc to nitroalkenes, using up to nine different nitroalkenes in a one pot procedure. The 18 products (9 times 2 enantiomers of nine different nitroalkanes) can be analyzed by chiral CG in a single run since on overlap in the peaks is observed. The obtained enantioselectivities are amongst the highest reported so far for the catalytic 1,4-addition

  多底物方法用于在一锅法中最多使用九种不同的硝基烯烃，将铜-亚铁酰胺催化的二乙基锌与硝基烯烃的对映选择性共轭加成反应。可以通过手性CG在一次运行中分析18种产物（9种不同硝基链烷烃的9对2对映体），因为观察到峰重叠。获得的对映选择性是迄今为止报道的将二烷基锌试剂催化1,4-加成到硝基烯烃中的最高对映选择性。
• Application of the Chiral Bis(phosphine) Monoxide Ligand to Catalytic Enantioselective Addition of Dialkylzinc Reagents to β-Nitroalkenes
  作者：Alexandre Côté,、Vincent N. G. Lindsay、André B. Charette

  DOI：10.1021/ol062792t

  日期：2007.1.1

  see text] Me-DuPHOS monoxide is shown to be a very effective ligand in the enantioselective copper-catalyzed addition of dialkylzinc reagents to beta-nitroalkenes providing access to chiral nitroalkanes. The major advantages of this process are high yields, broad and complementary substrate scope, and high enantioselectivities. The effect of achiral dummy ligands as an additive has also been documented

  [反应：见正文]在对映选择性铜催化的二烷基锌试剂与β-硝基烯烃的对映选择性铜催化加成反应中，Me-DuPHOS一氧化碳被证明是非常有效的配体。该方法的主要优点是高产率，广泛和互补的底物范围以及高对映选择性。非手性假配体作为添加剂的作用也已有文献记载。
• Enantioselective conjugate addition of primary dialkylzinc reagents to 2-aryl- and 2-heteroaryl-nitroolefins mediated by titanium-TADDOLates preparation of enantioenriched 2-aryl-alkylamines
  作者：Harald Schäfer、Dieter Seebach

  DOI：10.1016/0040-4020(94)01100-e

  日期：1995.2

  The addition of dialkylzinc to nitroolefins is catalyzed by Lewis acids such as MgBr2, MgI2, and chlorotitanates. Using the (R,R)-Ti-TADDOLates the addition of diethyl-, dibutyl-, and dioctyl zinc to 2-aryl-nitroethenes is shown to be enantioselective with yields near 90% and enantiomer ratios of ca. 9:1 (products 3-12; enantiomer enrichment by crystallization is possible in some cases). Reduction of the 2-aryl-nitroalkanes thus obtained by catalytic hydrogenation over Pd/C or Raney-Ni leads to the corresponding enantioenriched 2-aryl-alkylamines (products 13-21). The enantiopurity of the nitroalkanes and amines was determined by chromatography on chiral columns. The configuration of the products is assigned (S) by optical comparison and by analogy (comparison of five different types of physical data). The relative topicity of the process is unlike (ul = R,R/Si or S,S/Re).
• Chiral amidophosphane–copper-catalyzed asymmetric conjugate addition of dialkylzinc reagents to nitroalkenes
  作者：Fanny Valleix、Kazushige Nagai、Takahiro Soeta、Masami Kuriyama、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2005.05.070

  日期：2005.8

  The copper-amidophosphane-catalyzed asymmetric addition reaction of dialkylzinc reagents with beta-aryl and beta-alkylnitroalkenes afforded the corresponding nitroalkanes with moderate to good enantioselectivities (54-80% ee). The performance was highly dependent on the reaction procedure where the addition of nitroalkene to the mixture of copper-amidophosphane and dialkylzinc gave higher ee than the addition of dialkylzinc to a mixture of copper-amidophosphane and nitroalkene. (c) 2005 Elsevier Ltd. All rights reserved.
• Seebach, Dieter; Schaefer, Harald; Schmidt, Beat, Angewandte Chemie, 1992, vol. 104, # 12, p. 1680 - 1681
  作者：Seebach, Dieter、Schaefer, Harald、Schmidt, Beat、Schreiber, Martin

  DOI：——

  日期：——