1-(4-methoxyphenyl)ethyl 3,5-dinitrobenzoate | 88563-47-7

• 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: 1-(4-methoxyphenyl)ethyl 3,5-dinitrobenzoate
• CAS: 88563-47-7
• 化学式: C₁₆H₁₄N₂O₇
• 分子量: 346.296
• InChiKey: WBMLTCWJCPXIGP-UHFFFAOYSA-N

物化性质

• 沸点：
  499.1±40.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  121.81
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)ethyl 3,5-dinitrobenzoate 在 sodium azide 、 sodium acetate 作用下， 以 水 为溶剂， 反应 20.0h， 生成 1-(1-叠氮乙基)-4-甲氧基苯
  参考文献：
  名称：

  Carbocation lifetimes that are independent of carbocation stability: the reaction of α-substituted 4-methoxybenzyl carbocations

  摘要：

  α-甲氧基-4-甲氧基苄基碳正离子与溶剂三氟乙醇→水（50：50 v/v）反应，速率常数ks= 3 × 107 s→1；当碳正离子通过强吸电子α-CF3 取代基取代强给电子α-OMe 取代基而不稳定时，ks 增加不到两倍。

  DOI：

  10.1039/c39910000200
• 作为产物：
  描述：

  4-甲氧基-α-甲基苯甲醇 、 3,5-二硝基苯甲酰氯 在 吡啶 作用下， 以65%的产率得到1-(4-methoxyphenyl)ethyl 3,5-dinitrobenzoate
  参考文献：
  名称：

  具有大环腔的手性双卟啉受体插入芳香族化合物的分子识别

  摘要：

  手性二卟啉受体 1 具有用于插入芳香客体分子的大环腔，是由吡咯设计和合成的，分为五个步骤。结合常数 (Ka) ...

  DOI：

  10.1246/bcsj.20110230

文献信息

• Formation and stability of ring-substituted 1-phenylethyl carbocations
  作者：John P. Richard、Marc E. Rothenberg、William P. Jencks

  DOI：10.1021/ja00317a031

  日期：1984.3

  l'utilisation d'azoture et de thiolate en tant que reactifs de piegeage controlant la diffusion afin d'evaluer les constantes de vitesse des reactions des carbocations aryl-1 ethyles avec le solvant et ses composants en fonction de la structure du carbocation, la composition du solvant et la concentration en sel

  描述 de l'utilisation d'azoture et de thiolate entant que reactifs de piegeage controlant la diffusion afin d'evaluer les constantes de vitesse des反应 des carboccations aryl-1 ethyles avec le solvant et ses composants en fonction de la structure du carbocation,溶剂组合物和浓缩液
• General base catalysis of the addition of hydroxylic reagents to unstable carbocations and its disappearance
  作者：John P. Richard、William P. Jencks

  DOI：10.1021/ja00317a034

  日期：1984.3

  Etude de la catalyse basique generale de l'addition d'alcools aux carbocations aryl-1 ethyles

  Etude de la catalyze basique generale de l'addition d'alcools aux carboncations aryl-1 乙基
• The effects of .alpha.-substituents on the kinetic and thermodynamic stability of 4-methoxybenzyl carbocations: carbocation lifetimes that are independent of their thermodynamic stability
  作者：Tina L. Amyes、Ishmael W. Stevens、John P. Richard

  DOI：10.1021/jo00074a036

  日期：1993.10

  The following new rate constants for reaction of alpha-substituted 4-methoxybenzyl carbocations, 4-MeOC6H4CR1(R2)+, With a solvent of 50:50 (v/v) trifluoroethanol/water at 25-degrees-C and ionic strength 0.50 (NaClO4) are reported: 4-MeOC6H4CH(OMe)+, k(S) = 2.2 X 10(7) s-1; 4-MeOC6H4CH(N3)+, k(S) = 3.3 X 10(5) s-1; 4-MeOC6H4C(CH3)2+, k(S) = 1.3 x 10(7) s-1; 4-MeOC6H4CH(CO2Et)+, k(S) = 1.4 X 10(7) s-1; 4-MeOC6H4CCH3(CF3)+, k(S) = 2.5 x 10(7) s-1. The values of k(S) for reaction of 4-MeOC6H4CR1(R2)+ with 50:50 (v/v) trifluoroethanol/water are nearly independent of very large changes in the thermodynamic stability of these carbocations caused by the addition of a wide range of electron-withdrawing or electron-donating groups at the alpha-position. In the most extreme case, the change from an alpha-methoxy to two alpha-(trifluoromethyl) substituents leads to a 23 kcal/mol thermodynamic destabilization of 4-MeOCrH4CR1(R2)+ relative to the neutral azide ion adducts but a 5-fold decrease in its reactivity toward solvent. The data show that the effects of alpha-substituents on the kinetic stability of 4-MeOC6H4CR1(R2)+ are complex and do not parallel the thermodynamic stability of these carbocations. The results are explained by consideration of the polar and resonance effects of the alpha-substituents on both the thermodynamic driving force and the intrinsic barrier for capture of the carbocations by solvent. These reactions are a new example of the consequences of the ''principle of nonperfect synchronization''.41
• Reactions of substituted 1-phenylethyl carbocations with alcohols and other nucleophilic reagents
  作者：John P. Richard、William P. Jencks

  DOI：10.1021/ja00317a032

  日期：1984.3
• Molecular Recognition of Chiral Diporphyrin Receptor with a Macrocyclic Cavity for Intercalation of Aromatic Compounds
  作者：Tadashi Ema、Norichika Ura、Katsuya Eguchi、Takashi Sakai

  DOI：10.1246/bcsj.20110230

  日期：2012.1.15

  Chiral diporphyrin receptor 1, which has a macrocyclic cavity for the intercalation of aromatic guest molecules, was designed and synthesized from pyrrole in five steps. The binding constants (Ka) ...

  手性二卟啉受体 1 具有用于插入芳香客体分子的大环腔，是由吡咯设计和合成的，分为五个步骤。结合常数 (Ka) ...