3-hydroxy-2-(2-nitro-1-phenylethyl)cyclohex-2-enone | 92774-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-2-(2-nitro-1-phenylethyl)cyclohex-2-enone
• 英文别名: 3-hydroxy-2-(2-nitro-1-phenylethyl)cyclohex-2-en-1-one
• CAS: 92774-90-8
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: QHAJUFVCAGJIGM-UHFFFAOYSA-N

物化性质

• 沸点：
  452.0±45.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-(2-nitro-1-phenylethyl)cyclohex-2-enone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (E)-2-(hydroxyimino)-3-phenyl-2,3,6,7-tetrahydro benzofuran-4(5H)-one
  参考文献：
  名称：

  Hrnciar, Pavel; Culak, Igor, Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 6, p. 1421 - 1431

  摘要：

  DOI：
• 作为产物：
  描述：

  β-硝基苯乙烯 、 1,3-环己二酮 在 sodium 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以68%的产率得到3-hydroxy-2-(2-nitro-1-phenylethyl)cyclohex-2-enone
  参考文献：
  名称：

  Hrnciar, Pavel; Culak, Igor, Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 6, p. 1421 - 1431

  摘要：

  DOI：

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.