2-nitro-1-phenyl-1-phenylsulfonylethane | 87015-49-4

• 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: 2-nitro-1-phenyl-1-phenylsulfonylethane
• 英文别名: (2-nitro-1-(phenylsulfonyl)ethyl)benzene；(2-nitro-1-phenyl-ethyl)-phenyl sulfone；(2-Nitro-1-phenyl-aethyl)-phenyl-sulfon；[2-Nitro-1-(phenylsulfonyl)ethyl]benzene；[1-(benzenesulfonyl)-2-nitroethyl]benzene
• CAS: 87015-49-4
• 化学式: C₁₄H₁₃NO₄S
• 分子量: 291.328
• InChiKey: XMKJTJSZFKWLAH-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C
• 沸点：
  509.0±50.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-nitro-1-phenyl-1-phenylsulfonylethane 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 生成 β-硝基苯乙烯 、 苯亚磺酸
  参考文献：
  名称：

  活化砜的动力学研究

  摘要：

  反应速率和平衡位置由活化砜分解过程中释放的亚磺酸的 pH 静态滴定确定。这些值可以与 σ-Hammett 参数相关联。

  DOI：

  10.1002/ardp.19833160802
• 作为产物：
  描述：

  (2-nitro-1-phenylethyl)(phenyl)sulfane 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 23.0h， 以97%的产率得到2-nitro-1-phenyl-1-phenylsulfonylethane
  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

• Reaction of Arendiazonium Salts and SO₂with α-Nitroolefins
  作者：E. E. Bilaya、N. D. Obushak、A. M. Buchinskii、N. I. Ganushchak

  DOI：10.1023/b:rujo.0000034940.16955.8e

  日期：2004.2

  In reaction of beta-nitrostyrene and 2-(2-nitrovinyl)furan with arenediazonium chlorides and SO2 in the presence of copper(H) chloride products were obtained resulting from addition of arylsulfonyl group and a hydrogen atom across the C=C bond: 2-nitro-1-phenylethylsulfonylarenes and 2-(1-aryisulfonyl-2-nitroethyl)furans respectively. An anion-radical mechanism of the reaction was suggested.
• The Preparation of Some Aryl Aminoalkyl Sulfides and Sulfones^1,2
  作者：Louis F. Cason、Calvin C. Wanser

  DOI：10.1021/ja01145a051

  日期：1951.1
• Aleksiev, D. I.; Ivanova, S.; Tashkova, Kr., Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 85, # 1-4, p. 73 - 76
  作者：Aleksiev, D. I.、Ivanova, S.、Tashkova, Kr.

  DOI：——

  日期：——
• TSAJKOVA S. I.; ALEKSIEV D. I., GOD. VISSH. XIM.-TEXNOL. IN-T. BURGAS, 20,(1985) N 2, 37-41
  作者：TSAJKOVA S. I.、 ALEKSIEV D. I.

  DOI：——

  日期：——
• 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.