1-phenyl-2-nitroethyl benzyl ether | 174318-87-7

• 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 benzyl ether
• 英文别名: (1-(benzyloxy)-2-nitroethyl)benzene；(2-Nitro-1-phenylethoxy)methylbenzene
• CAS: 174318-87-7
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: VYEVKRKHTOQWQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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 benzyl ether 在 platinum on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以27%的产率得到(+/-)-2-benzyloxy-2-phenylethylamine
  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 、 苯甲醇钠 以 苯甲醇 为溶剂， 反应 0.25h， 以66%的产率得到1-phenyl-2-nitroethyl benzyl 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

• Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes
  作者：James C. Anderson、Andreas S. Kalogirou、Graham J. Tizzard

  DOI：10.1016/j.tet.2014.10.042

  日期：2014.12

  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.
• β-Alkoxy-substituted phenethylamines: a family of compounds potentially active at the dopamine and α-adrenergic receptors
  作者：H.E. Katerinopoulos、N Tagmatarchis、G Zaponakis、N Kefalakis、K Kordatos、M Spyrakis、K Thermos

  DOI：10.1016/0223-5234(96)88314-0

  日期：1995.1

  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.