2,6-di-tert-butyl-4-(1-(4-methoxyphenyl)-2-nitropropyl)phenol

• 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: 2,6-di-tert-butyl-4-(1-(4-methoxyphenyl)-2-nitropropyl)phenol
• 英文别名: 2,6-Ditert-butyl-4-[1-(4-methoxyphenyl)-2-nitropropyl]phenol
• 化学式: C₂₄H₃₃NO₄
• 分子量: 399.53
• InChiKey: RESAFIYHWQDYMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-di-tert-butyl-4-(4-methoxybenzylidene)-cyclohexa-2,5-dienone 、 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.5h， 以55%的产率得到2,6-di-tert-butyl-4-(1-(4-methoxyphenyl)-2-nitropropyl)phenol
  参考文献：
  名称：

  Nucleophilicities of Nitroalkyl Anions

  摘要：

  The kinetics of the reactions of eight nitroalkyl anions (nitronate anions) with benzhydrylium ions and quinone methides in DMSO and water were investigated photometrically. The second-order rate constants were found to follow a Ritchie constant selectivity relationship with slightly smaller selectivities than those observed previously for other carbanions and O or N nucleophiles. Evaluation of the kinetic data by the correlation equation log k (20 degreesC) = s(N + E) yields the nucleophilicity parameters, (N), which allow a comparison of the nucleophilicities of nitronates with those of other classes of compounds. Although the aliphatic nitronates la-c are more nucleophilic than the aromatic representatives Id-h in DMSO, hydration reduces the nucleophilicities of aliphatic nitronates by a factor of 1 million, which is considerably greater than the reduction of the reactivities of the aromatic nitronates with the consequence that aromatic nitronates are more nucleophilic in water than aliphatic ones. The nucleophilic reactivities of nitronates are only slightly affected by substituent variation in DMSO and even less so in aqueous solution, which is considered to be the reason for the unusual rate equilibrium relationships, the so-called nitroalkane anomaly. Outersphere electron transfer does not occur in any of the reactions that were investigated.

  DOI：

  10.1021/jo048773j

文献信息

• Reactions of Nitroheteroarenes with Carbanions: Bridging Aromatic, Heteroaromatic, and Vinylic Electrophilicity
  作者：Florian Seeliger、Sylwia Błażej、Sebastian Bernhardt、Mieczysław Mąkosza、Herbert Mayr

  DOI：10.1002/chem.200800329

  日期：2008.7.7

  reactive than nitrobenzene. Among the five-membered heterocycles 2-nitrothiophene is the most active followed by nitroimidazoles and 4-nitropyrazole. Nitropyrroles are the least electrophilic nitroheteroarenes with reactivities comparable to nitrobenzene. Quantum chemically calculated methyl anion affinities (B3LYP/6-311G(d,p)//B3LYP/6-31G(d)) of the nitroarenes correlated only moderately with the partial

  已确定氯甲基苯基砜（1-）的阴离子被各种硝基杂芳烃（例如硝基吡啶，硝基吡咯，硝基咪唑，2-硝基噻吩和4-硝基吡唑）的取代亲核取代（VNS）的相对速率常数通过竞争实验。结果表明，硝基吡啶的活性比硝基苯高大约四个数量级。在五元杂环中，2-硝基噻吩活性最高，其次是硝基咪唑和4-硝基吡唑。硝基吡咯是亲电性最低的硝基杂芳烃，其反应性与硝基苯相当。量子化学计算的硝基芳烃的甲基阴离子亲和力（B3LYP / 6-311G（d，p）// B3LYP / 6-31G（d））仅与部分相对速率常数适度相关。这些活性与硝基芳烃的LUMO能的相关性甚至更差。通过测量1-硝基芳烃和二乙基亚芳基丙二酸酯10的二阶速率常数，可以将硝基杂芳烃的亲电反应性与基于线性自由能关系log k（K）的综合亲电等级联系起来。 20摄氏度）= s（N + E）。
• Constant Selectivity Relationships of Addition Reactions of Carbanions
  作者：Roland Lucius、Herbert Mayr

  DOI：10.1002/1521-3773(20000602)39:11<1995::aid-anie1995>3.0.co;2-e

  日期：2000.6.2
• Nucleophilicities of Nitroalkyl Anions
  作者：Thorsten Bug、Tadeusz Lemek、Herbert Mayr

  DOI：10.1021/jo048773j

  日期：2004.10.1

  The kinetics of the reactions of eight nitroalkyl anions (nitronate anions) with benzhydrylium ions and quinone methides in DMSO and water were investigated photometrically. The second-order rate constants were found to follow a Ritchie constant selectivity relationship with slightly smaller selectivities than those observed previously for other carbanions and O or N nucleophiles. Evaluation of the kinetic data by the correlation equation log k (20 degreesC) = s(N + E) yields the nucleophilicity parameters, (N), which allow a comparison of the nucleophilicities of nitronates with those of other classes of compounds. Although the aliphatic nitronates la-c are more nucleophilic than the aromatic representatives Id-h in DMSO, hydration reduces the nucleophilicities of aliphatic nitronates by a factor of 1 million, which is considerably greater than the reduction of the reactivities of the aromatic nitronates with the consequence that aromatic nitronates are more nucleophilic in water than aliphatic ones. The nucleophilic reactivities of nitronates are only slightly affected by substituent variation in DMSO and even less so in aqueous solution, which is considered to be the reason for the unusual rate equilibrium relationships, the so-called nitroalkane anomaly. Outersphere electron transfer does not occur in any of the reactions that were investigated.