3,5-二(2-甲基-2-丙基)-4-硝基联苯 | 143726-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-二(2-甲基-2-丙基)-4-硝基联苯
• 中文别名: D-α-甲基亮氨酸盐酸
• 英文名称: 3,5-Di-tert-butyl-4-nitro-1,1'-biphenyl
• 英文别名: 1,3-ditert-butyl-2-nitro-5-phenylbenzene
• CAS: 143726-80-1
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: IPFAZYLCWVGYMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-di-tert-butylbiphenyl-4-ylamine 在 叔丁基过氧化氢 、 cobalt(II) 1,6-bis(2-hydroxyphenyl)-2,5-diaza-3,3,4,4-tetramethylhexa-1,5-diene 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以24%的产率得到2,6-Ditert-butyl-4-tert-butylperoxy-4-phenylcyclohexa-2,5-dien-1-imine
  参考文献：
  名称：

  Cobalt Schiff Base Complex-Catalyzed Oxidation of Anilines with tert-Butyl Hydroperoxide

  摘要：

  Cobalt Schiff base complexes [Co(SB)] catalyze the oxidation of anilines (1) with tert-butyl hydroperoxide to give nitrobenzenes 2 and 4-(tert-butylperoxy)-2,5-cyclohexadien-1-imine derivatives 3 in yield distributions depending on the substitution mode of the substrate. 4-Alkyl- and 4-aryl-2,6-di-tert-butylanilines gave mixtures of 2 and 3, where the higher the bulkiness of the 4-substituent, the higher the yield of 2. With 2,4,6-trimethylaniline, the ratio of oxidations of the nitrogen and C-4 atoms was almost the same; but a hydrolyzed product 5 of the imine was obtained. 2,4,6-Triphenylaniline gave only 2. Nitrobenzene derivatives were also obtained from 2,6-dialkylanilines and 4-substituted anilines. The catalytic activity of Co(SB) depended on the nature of the SB ligand: the formal potential E degrees and steric factors seem to affect the reaction rate. Kinetic studies showed that the key step may involve hydrogen abstraction from the aniline, presumably by t-BuO(.) generated from homolytic decomposition of initially formed Co-III(SB)(OO-t-Bu). A precursor of 2 was found to be the nitrosobenzene derivative.

  DOI：

  10.1021/jo952198p

文献信息

• From mutagenic to non-mutagenic nitroarenes: effect of bulky alkyl substituents on the mutagenic activity of 4-nitrobiphenyl in Salmonella typhimurium
  作者：Markus Klein、Ulrike Voigtmann、Torsten Haack、Lothar Erdinger、Gernot Boche

  DOI：10.1016/s1383-5718(00)00012-7

  日期：2000.4

  This reduction of mutagenicity is correlated with deviations from the coplanar orientation of the nitro group relative to the aromatic plane. Since a comparable decrease of mutagenicity for the nitroso compounds (4NOBp and 3-tertbutyl-4NOBp) was not observed, the first reduction step of non-planar nitro groups must be inhibited. Alkyl groups in the 2'-position of 4NBp (2'-methyl-, 2'-ethyl-, 2'-isopropyl-

  合成了11种烷基取代的4-硝基联苯（4NBp）和两种相应的亚硝基化合物，并测试了鼠伤寒沙门氏菌TA98和TA100菌株的诱变能力。邻位被硝基取代的化合物的诱变性（3-甲基-，3-乙基-，3-异丙基-，3-叔丁基-，3、5-二乙基-，3,5-二异丙基-和3,5-在两个测试菌株中，随着烷基取代基的空间需求的增长，二叔丁基-4NBp）降低。受空间影响最大​​的化合物即使在最高浓度下也不会引起突变。致突变性的降低与硝基相对于芳族平面的共面取向的偏离有关。由于未观察到亚硝基化合物（4NOBp和3-叔丁基-4NOBp）致突变性的可比下降，必须抑制非平面硝基的第一步还原。4NBp（2'-甲基-，2'-乙基-，2'-异丙基和2'，4'，6'-三甲基-4NBp）2'-位处的烷基也随着大小的增加而降低了诱变活性并将其完全清除掉，成为受空间最大阻碍的物种（2'-异丙基-，2'，4'，6'-三甲基-4NBp）。在
• Co(salen) catalyzed oxidation of 2,4,6-trisubstituted anilines with tert-butylhydroperoxide
  作者：Akira Nishinaga、Stefan Fo¨rster、Emerich Eichhorn、Bernd Speiser、Anton Rieker

  DOI：10.1016/s0040-4039(00)60100-4

  日期：1992.7

  Co(salen) catalyzed oxidation of 2,4,6-trisubstituted (preferentially 2,6-di-tert-butylated) anilines with tert-butylhydroperoxide gives 4-tert-butylperoxy-2,5-cyclohexadien-1-imine and nitrobenzene derivatives. The relative ratio of the products depends on the nature of the substituents in the substrate.