2-nitro-2-(4-nitrophenyl)propane | 3276-35-5

• 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-2-(4-nitrophenyl)propane
• 英文别名: p-nitro-α-nitrocumene；α,p-dinitrocumene；2-Nitro-2-<4-nitrophenyl-propan；p-(1-Methyl-1-nitroethyl)nitrobenzol；2-Nitro-2-(4-nitrophenyl)-propan；α,p-Dinitrocumol；1-nitro-4-(2-nitropropan-2-yl)benzene
• CAS: 3276-35-5
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: TVMFOXFWIMATIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-nitro-2-(4-nitrophenyl)propane 以 六甲基磷酰三胺 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 对硝基异丙基苯
  参考文献：
  名称：

  Norris, Robert K.; Wright, Timothy A., Australian Journal of Chemistry, 1985, vol. 38, # 7, p. 1107 - 1116

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-氯丙烷-2-基)-4-硝基苯 在 sodium nitrite 作用下， 以 二甲基亚砜 为溶剂， 反应 120.0h， 以91%的产率得到2-nitro-2-(4-nitrophenyl)propane
  参考文献：
  名称：

  Substitution reactions which proceed via radical anion intermediates. 29. Electron-transfer substitution reactions: p-nitrocumyl system

  摘要：

  DOI：

  10.1021/jo00378a008

文献信息

• Electron transfer reactivity in 5-nitrouracil series
  作者：Michel P. Crozet、Armand Gellis、Christian Pasquier、Patrice Vanelle、Jean-Pierre Aune

  DOI：10.1016/0040-4039(94)02304-t

  日期：1995.1

  shown to react with various reductive alkylating agents such as p-nitrobenzyl chloride and dinitropropane by an SRN1 mechanism to give new potentially bioactive 5-nitrouracil derivatives. 1,3-Dimethyl-5-nitro-6-chloromethyluracil also reacts by an SRN1 mechanism with 2-nitropropane anion to afford a new uracil derivative bearing a trisubstituted ethylenic double bond at the 6-position.

  1，3，6-三甲基-5-硝基尿嘧啶的钠盐显示通过S RN 1机理与各种还原性烷基化剂（例如对硝基苄基氯和二硝基丙烷）反应生成新的具有潜在生物活性的5-硝基尿嘧啶衍生物。1，3-二甲基-5-硝基-6-氯甲基尿嘧啶也通过S RN 1机理与2-硝基丙烷阴离子反应，得到新的尿嘧啶衍生物，其在6-位带有三取代的烯键式双键。
• Concerning the mechanism of displacement of nitro groups from activated aromatic systems
  作者：Donald B. Denney、Dorothy Z. Denney、Airan Jun Perez

  DOI：10.1016/s0040-4020(01)81276-x

  日期：1993.5

  The photostimulated reactions of p-nitrobenzophenone and p-nitrobenzonitrile with a variety of nucleophiles have been investigated. Displacement of the nitro group is observed in all cases. The rates of the reactions were measured by FT-IR. The rates were slowed by substances such as sulfur, air, Galvinoxyl and p-benzoquinone. In several cases rates of loss of starting material were monitored by quenching

  研究了对硝基二苯甲酮和对硝基苯甲腈与各种亲核试剂的光刺激反应。在所有情况下均观察到硝基的置换。反应速率通过FT-IR测量。诸如硫，空气，加尔维诺尔和对苯醌等物质使速率降低。在几种情况下，通过淬灭反应混合物并分离产物和起始原料来监测起始原料的损失速率。这些反应在抑制剂存在下也显示出对其速率的抑制。这些结果表明反应是连锁过程。结论是，底物被转化成它们相应的自由基阴离子，然后它们在双分子置换反应中与亲核试剂反应。替代机制，
• A new synthetic approach for novel 4-substituted-5-nitroimidazoles
  作者：Maxime D. Crozet、Patricia Perfetti、Mustapha Kaafarani、Patrice Vanelle、Michel P. Crozet

  DOI：10.1016/s0040-4039(02)00767-0

  日期：2002.6

  A new synthetic approach, involving an SRN1 reaction of the anion of 1-methyl-4-phenylsulfonyl-methyl-5-nitro-1H-imidazole with 2,2-dinitropropane and a radical anion or a concerted radical reductive elimination of sulfonyl and nitro groups affords an original 5-nitroimidazole bearing a trisubstituted ethylenic double bond at 4-position.

  一种新的合成方法，涉及1-甲基-4-苯基磺酰基-甲基-5-硝基-1 H-咪唑的阴离子与2，2-二硝基丙烷的S RN 1反应和自由基阴离子或协同消除自由基磺酰基和硝基基团提供了一个原始的5-硝基咪唑，其在4-位带有一个三取代的烯键式双键。
• Nucleophilic Substitution Reactions of Tetrabutylammonium aci-Nitronates with p-Substituted Nitrobenzenes
  作者：RK Norris、D Randles

  DOI：10.1071/ch9792413

  日期：——

  The reactions of tetrabutylammonium aci-nitronates with p-dinitrobenzene in dimethyl sulfoxide, benzene or acetone proceed far more rapidly than the reactions of the corresponding lithium salts and give, in unhindered cases, good yields of C-arylates, e.g. p-(1-methyl-1-nitroethyl)nitrobenzene (in 73-89% yields) and p-nitro(l,3,3-trimethyl-1-nitrobuty1)benene (in 70% yield). With more sterically hindered nitronates, O-arylation increases, giving phenols and ketoxime O-p-nitrophenyl ethers, presumably derived from the novel, intermediate p-nitrophenyl aci-nitronate esters. aci-Nitronate ions with more than two β-methyl groups gave no C-arylation. Similar results were obtained with p-fluoronitrobenzene and p-nitrobenzonitrile, A mechanism for the conversion of the intermediate aci-nitronate esters into the ketoxime ethers is proposed.

  四丁基硝酸铵与对二硝基苯的反应 与对二硝基苯在二甲亚砜、苯或丙酮中的反应要比 反应要比相应锂盐的反应迅速得多，而且在无阻碍的情况下还能得到 例如对（1-甲基-1-硝基乙基）硝基苯（收率为 73-89%）和对硝基（l,3,3-三甲基-1-硝基丁 1）苯（收率为 70%）。对于立体受阻较大的硝酸酯，O-芳基化作用会增加，从而产生苯酚和酮。 酚和酮肟 O-对硝基苯醚。 对硝基苯基 Aci-Nitronate 酯。 两个以上 β-甲基的 aci-Nitronate 离子不会产生 C-芳基化反应。 对氟硝基苯和对硝基苯腈也得到了类似的结果。 中间体艾氏硝酸 提出了将中间体酰基硝酸酯转化为酮肟醚的机理。
• The kinetics and mechanism of the reaction of p-nitrocumyl bromide with nitrite ions in dimethyl sulfoxide. Evidence for a non-chain reaction giving a high nitro/nitrite ratio in the product
  作者：Stuart W. Paine、John H. Ridd

  DOI：10.1039/p29960002577

  日期：——

  The reaction of p-nitrocumyl bromide (RBr) with sodium nitrite in [2H6]dimethyl sulfoxide gives none of the conventional evidence for an SRN1 chain reaction but the initial values of the [RNO2]/[RONO] ratio (2.5–5) are far higher than would be expected for the attack of a nitrite ion on the carbocation R+ and increase with the concentration of nitrite ions. The high values of [RNO2]/[RONO] are considered to derive from a mechanism in which a nitrite ion attacks a π-complex derived from the carbocation R+ and a second nitrite ion. This interpretation is supported by a kinetic term that is second order with respect to nitrite ions. An attempt to provide evidence for alternative radical pair intermediates from 15N CIDNP effects was unsuccessful.

  对硝基二茂溴(RBr)与亚硝酸钠在[2H6]二甲基亚砜中的反应没有给出 SRN1 链式反应的常规证据，但[RNO2]/[RONO]比值（2.5-5）的初始值远高于亚硝酸根离子攻击碳化合物 R+ 的预期值，并且随着亚硝酸根离子浓度的增加而增加。据认为，[RNO2]/[RONO]的高值源于亚硝酸根离子攻击由碳位 R+ 和第二个亚硝酸根离子生成的 π-复合物的机制。这一解释得到了与亚硝酸根离子有关的二阶动力学项的支持。试图从 15N CIDNP 效应中提供替代自由基对中间体的证据，但没有成功。