β-methyl-β-nitro-α-phenylstyrene | 15795-69-4

• 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: β-methyl-β-nitro-α-phenylstyrene
• 英文别名: 2-nitro-1,1-diphenylpropene；1,1-Diphenyl-2-nitro-propen-(1)；2-Nitro-1,1-diphenyl-propen；1,1-Diphenyl-2-nitropropen；1,1'-(2-Nitroprop-1-ene-1,1-diyl)dibenzene；(2-nitro-1-phenylprop-1-enyl)benzene
• CAS: 15795-69-4
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: AWDYUVQYWATBHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  β-methyl-β-nitro-α-phenylstyrene 在 亚磷酸三乙酯 作用下， 反应 2.0h， 以100%的产率得到2-甲基-3-苯基-1H-吲哚
  参考文献：
  名称：

  Reactions of ethyl phosphites with .beta.-nitrostyrenes. The role of nitrosoalkenes as intermediates

  摘要：

  3-Phenyl-2-substituted-indoles are formed in high yields in the reaction of Ph2C=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C while reaction with (EtO)2PO-/(EtO)2P(O)H at room temperature forms the aziridines 1 with R = H, Me, Ph. 2,2-Diphenyl-3-substituted-2H-azirines formed by deoxygenation of the Michael-type adducts are postulated as intermediates. Reactions of PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C or (EtO)2PO-/(EtO)2P(O)H at room temperature give products resulting from the addition of the phosphorus nudeophile at the benzylidene carbon atom. Evidence for the formartion of cyclic structures with pentacoordinated phosphorus atoms is presented for the reaction of Ph2C=C(Me)NO2 with (EtO)2PO-/EtO)2P(O)H and for PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P. The Michael-type adducts PhCH[P(O)(OEt)2]CH(R)NO2 (R = Me, Ph) undergo reaction upon treatment with aqueous base at 80-100-degrees-C followed by acidification to yield the 3-(diethoxyphosphinyl)-2-R-N-hydroxyindoles. 4-(Diethoxyphosphinyl)-3-R-4H-1,2-benzoxazines (13, R = Me, Ph) are formed by reaction with 85% H2SO4 Of the adducts of PhCH=C(R)NO2 with (EtO)2PO (R = Me) or (EtO)3P (R = Ph).

  DOI：

  10.1021/jo00050a026
• 作为产物：
  描述：

  1-Acetoxy-1.1-diphenyl-2-nitro-propan 在 硫酸 、 溶剂黄146 作用下， 生成 β-methyl-β-nitro-α-phenylstyrene
  参考文献：
  名称：

  Nitrations with Acetyl Nitrate. III. Nitration with 1,1-Diarylalkenes¹

  摘要：

  DOI：

  10.1021/jo01056a014

文献信息

• Generation of nitroalkanes, hydroximoyl halides and nitrile oxides from the reactions of β-nitrostyrenes with Grignard or organolithium reagents
  作者：Ching-Fa Yao、Kuo-Hsi Kao、Ju-Tsung Liu、Cheng-Ming Chu、Yeh Wang、Wen-Chang Chen、Yu-Mei Lin、Wen-Wei Lin、Ming-Chung Yan、Jing-Yuan Liu、Ming-Ching Chuang、Jin-Lien Shiue

  DOI：10.1016/s0040-4020(97)10356-8

  日期：1998.1

  products 6 and/or 7 are observed if the nitronates, generated from the substrate 1a, are added to 85% aqueous H2SO4 but only the hydrolyzed carboxylic acids 9 are generated when the β-nitrostyrenes 2 are reacted with Grignard reagents and worked up under the same condition. The nitrile oxides 7 can undergo 1,3-dipolar cycloaddition with alkenes or alkynes to generate 2-isoxazolines or isoxazoles. A one-pot

  β型硝基苯乙烯1或2与格氏或有机锂试剂反应在乙醚或THF溶液由1,4-加成中间nitronates以产生甲。当用稀盐酸处理A时，获得高产率的硝基烷3（和肟4）或5。当将中间体A缓慢加入到冰冷的浓氢卤酸中时，可以分离出羟甲酰卤6、8或一氧化氮7。如果从基材1a产生的硝酸盐观察到相同的产物6和/或7。将β-硝基苯乙烯2加入到85％的H 2 SO 4水溶液中，但是当β-硝基苯乙烯2与格氏试剂反应并在相同条件下进行后处理时，仅产生水解的羧酸9。腈氧化物7可与烯烃或炔烃进行1，3-偶极环加成反应以生成2-异恶唑啉或异恶唑。据报道，通过分子内一氧化氮-烯烃环加成反应可以一锅合成[n，3,0]双环（n = 3或4）化合物23-27。
• Titanium(III) Chloride Mediated Reduction of 1-Nitro-2-phenylethenes
  作者：Akira Sera、Shoji Fukumoto、Masako Tamura、Kiyoshi Takabatake、Hiroaki Yamada、Kuniaki Itoh

  DOI：10.1246/bcsj.64.1787

  日期：1991.6

  nes (β-nitrostyrenes) with aqueous titanium(III) chloride afforded substituted pyrroles in addition to the expected reduction products, oximes and carbonyl compounds. 2-Substituted 1-nitro-2-phenylethenes yielded divinylamine derivatives instead of pyrroles. The reaction mechanism has been rationalized by taking account of the electron transfer from titanium(III) species to the nitro olefins, followed

  除了预期的还原产物、肟和羰基化合物之外，1-硝基-2-苯基乙烯（β-硝基苯乙烯）与氯化钛（III）水溶液的反应还提供取代的吡咯。2-取代的 1-硝基-2-苯基乙烯产生二乙烯基胺衍生物而不是吡咯。通过考虑从钛 (III) 物种到硝基烯烃的电子转移，随后进行质子化、二聚、环化和/或水解，使反应机制合理化。
• Titanium Trichloride Mediated Reduction of Nitrostyrenes
  作者：Akira Sera、Shoji Fukumoto、Takako Yoneda、Hiroaki Yamada

  DOI：10.3987/r-1986-03-0697

  日期：——
• Grant, Richard D.; Pinhey, John T.; Rizzardo, Ezio, Australian Journal of Chemistry, 1984, vol. 37, # 6, p. 1217 - 1229
  作者：Grant, Richard D.、Pinhey, John T.、Rizzardo, Ezio

  DOI：——

  日期：——
• SERA, AKIRA;YAMAUCHI, HIDEMI;YAMADA, HIROAKI;ITOH, KUNIAKI, SYNLETT.,(1990) N, C. 477-478
  作者：SERA, AKIRA、YAMAUCHI, HIDEMI、YAMADA, HIROAKI、ITOH, KUNIAKI

  DOI：——

  日期：——