1-phenyl-2-nitroethyl methyl ether | 3532-58-9

• 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-phenyl-2-nitroethyl methyl ether
• 英文别名: (1-methoxy-2-nitroethyl)benzene；1-Methoxy-2-nitro-1-phenyl-aethan；1-Nitro-2-phenylaethylmethylaether；Methyl-<2-nitro-1-phenyl-aethyl>-aether；1²-Nitro-1¹-methoxy-1-aethyl-benzol；(β-Nitro-α-methoxy-aethyl)-benzol；Methyl-(2-nitro-1-phenyl-aethyl)-aether；methyl-(2-nitro-1-phenyl-ethyl)-ether
• CAS: 3532-58-9
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: MZEDLXQCIIQKGV-UHFFFAOYSA-N

物化性质

• 沸点：
  90-91 °C(Press: 0.3 Torr)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-phenyl-2-nitroethyl methyl ether 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以42%的产率得到2-methoxy-2-phenylethan-1-amine
  参考文献：
  名称：

  β-Alkoxy-substituted phenethylamines: a family of compounds potentially active at the dopamine and α-adrenergic receptors

  摘要：

  A series of beta-alkoxy-substituted phenethylamines were synthesized and tested for their affinity at the D-1 and D-2 dopaminergic receptors and the alpha(1) and alpha(2) adrenoceptors. None of the tested compounds exhibited D-2 receptor affinity. Among the nonhydroxylated compounds that were resolved to their antipodes, the (-)-enantiomers generally showed a moderate but distinct activity at the alpha(2) receptor. Ring hydroxylation appears to be a necessary requirement for D-1, activity. These results are discussed in terms of the structural elements of the tested drugs as compared to those of known active compounds.

  DOI：

  10.1016/0223-5234(96)88314-0
• 作为产物：
  描述：

  β-硝基苯乙烯 、 sodium methylate 以 甲醇 为溶剂， 反应 0.25h， 以37%的产率得到1-phenyl-2-nitroethyl methyl ether
  参考文献：
  名称：

  Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes

  摘要：

  The conjugate addition nitro-Mannich reactions of ethyl-beta-nitroacrylate (1) and beta-nitrostyrene (2) with electron rich aromatic nucleophiles, stabilized carbanions, alcohols, amines, thiols, and diphenyl phosphine oxide were investigated. The one pot conjugate addition nitro-Mannich reaction was unsuccessful except for the addition of alkoxides to 2 in alcohol as solvent. Isolation of the conjugate addition products followed by deprotonation with (BuLi)-Bu-n and treatment with a simple imine in the presence of TFA led to beta-nitroamine derived products. Products derived from 1 spontaneously cyclised in only a few examples and on the whole led to inherently unstable products. Products derived from 2 were isolated as their trifluoroacetamides, gave good yields of single diastereoisomers for aromatic and alkoxide nucleophiles and the structures were verified by single crystal X-ray crystallography. Products derived from amine nucleophiles were isolated in low yields while sulfur nucleophiles gave poor diastereoselectivities. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.042

文献信息

• On-water magnetic NiFe₂O₄ nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes
  作者：Soumen Payra、Arijit Saha、Subhash Banerjee

  DOI：10.1039/c6ra21160g

  日期：——

  Here, we have demonstrated the Michael addition of active methylene compounds, aromatic/aliphatic amines, thiols and alcohols to conjugated alkenes using magnetic nano-NiFe2O4 as reusable catalyst in water. Nano-NiFe2O4 efficiently catalyzed the formation of C–C and C–X (X = N, S, O etc.) bond through 1,4-addition reactions.

  在这里，我们已经证明了使用磁性纳米NiFe 2 O 4作为在水中可重复使用的催化剂将活性亚甲基化合物，芳香族/脂肪族胺，硫醇和醇的迈克尔加成到共轭烯烃上。纳米NiFe 2 O 4通过1，4-加成反应有效催化了CC和CX （X = N，S，O等）键的形成。
• The Addition Reaction of Dinitrogen Trioxide with Cinnamyl Acetate
  作者：Yoshie Kurihara、Kazuo Yamagishi

  DOI：10.1246/bcsj.38.1327

  日期：1965.8

  This study of the reaction between dinitrogen trioxide and cinnamyl acetate has indicated that the 3-acetoxy-2-nitro-1-phenyl-1-propylnitrite (IIb) is formed, in addition to 3-acetoxy-1 - nitroso- 2 -nitro - 1 - phenylpropane (IIa), in yield depending on the experimental conditions. Those products have been transformed in good yields into 1, 3-dimethoxy-2-nitro-1-phenylpropane, from which dl-eryth

  对三氧化二氮和乙酸肉桂酯之间反应的研究表明，除了 3-乙酰氧基-1-亚硝基-2-硝基之外，还形成了 3-乙酰氧基-2-硝基-1-苯基-1-丙基亚硝酸盐 (IIb) - 1 - 苯丙烷 (IIa)，产率取决于实验条件。这些产品已以良好的收率转化为 1, 3-二甲氧基-2-硝基-1-苯基丙烷，从中合成了 dl-erythro-2-amino-1-(p-nitrophenyl)-1, 3-propanediol。
• 1,3-Dipolar addition of nitrones to symmetrically substituted allenes: for the determination of absolute configuration of chiral allenes by NMR spectroscopy
  作者：Takahiro Kawai、Ko-hei Kodama、Takashi Ooi、Takenori Kusumi

  DOI：10.1016/j.tetlet.2004.03.161

  日期：2004.5

  5-Methyl-5-phenylpyrroline N-oxide was proved to be a useful 1,3-dipole for determining the absolute configuration of chiral allenes by means of NMR spectroscopy.

  5-甲基-5-苯基吡咯啉N-氧化物被证明是一种有用的1,3-偶极子，用于通过NMR光谱测定手性烯丙基的绝对构型。
• Rosenmund, Chemische Berichte, 1913, vol. 46, p. 1043
  作者：Rosenmund

  DOI：——

  日期：——
• Mannich; Walther, Archiv der Pharmazie, 1927, p. 7
  作者：Mannich、Walther

  DOI：——

  日期：——