| 142581-66-6

• CAS: 142581-66-6
• 化学式: CF₃O₃S*C₁₇H₂₁N₂
• 分子量: 402.438
• InChiKey: LFMFPNRLJRBAEC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 三乙胺-硼烷 作用下， 以 二氯甲烷 为溶剂， 生成 双[4-(二甲氨基)苯基]甲烷
  参考文献：
  名称：

  Kinetics and Mechanism of the Reactions of Amine Boranes with Carbenium Ions

  摘要：

  AbstractThe kinetics of the reactions of trialkylamine boranes and pyridine boranes with benzhydryl cations have been determined photometrically. Second‐order rate laws are obeyed, first‐order with respect to amine borane concentration and first‐order with respect to carbocation concentration. As for other reactions of carbocations with neutral nucleophiles, the rates of these reactions are only slightly affected by solvent polarity. The structure—reactivity relationships and kinetic isotope effects are in accord with a polar mechanism proceeding through a transition state where the migrating hydride is partly bound to the entering carbon and to the leaving boron atom. The rate constants correlate linearly with the electrophilicity parameters E of the carbenium ions. It is therefore possible to use the linear free enthalpy relationship logk2 = s(E+N) for determining nucleophilicity parameters N for the amine boranes and to compare their hydride‐donating abilities with those of other non‐charged hydride donors (silanes, germanes, stannanes, and dihydropyridines).

  DOI：

  10.1002/chem.19970030808

文献信息

• How Nucleophilic Are Diazo Compounds?
  作者：Thorsten Bug、Manfred Hartnagel、Clemens Schlierf、Herbert Mayr

  DOI：10.1002/chem.200304913

  日期：2003.9.5

  eight diazo compounds 1 a-g were investigated photometrically in dichloromethane. The nucleophilicity parameters N and slope parameters s of these diazo compounds were derived from the equation log k (20 degrees C)=s (E+N) and compared with the nucleophilicities of other pi systems (alkenes, arenes, silyl enol ethers, silyl ketene acetals). It is shown that the nucleophilic reactivities of diazo compounds

  在二氯甲烷中用光度法研究了苯甲基阳离子与八种重氮化合物1ag的反应动力学。这些重氮化合物的亲核参数N和斜率参数s从等式log k（20摄氏度）= s（E + N）导出，并与其他pi系统（烯烃，芳烃，甲硅烷基烯醇醚，甲硅烷基）的亲核性进行比较乙烯酮缩醛）。结果表明，重氮化合物的亲核反应活性覆盖了十多个数量级，与低反应性末端的苯乙烯和高反应性末端的烯胺的亲核反应性相当。这些反应的决定速率的步骤是重氮碳原子上的亲电子进攻，以产生重氮离子，重氮离子迅速失去氮。
• Structure–Nucleophilicity Relationships for Enamines
  作者：Bernhard Kempf、Nathalie Hampel、Armin R. Ofial、Herbert Mayr

  DOI：10.1002/chem.200204666

  日期：2003.5.23

  acetals) and carbanions. It is shown that the nucleophilic reactivities of enamines cover more than ten orders of magnitude, comparable to enol ethers on the low reactivity end and to carbanions on the high reactivity end. Since the products of N-attack are thermodynamically less stable than the reactants, the observed rate constants refer to the formation of the carbon bond;carbon bonds. In some cases

  在二氯甲烷中用光度法研究了苯甲基阳离子与22种烯胺，3种吡咯和3种吲哚的反应动力学。这些富含电子的pi系统的亲核参数N和斜率参数s从等式log k（20摄氏度）= s（E + N）导出，并与其他pi系统（甲硅烷基烯醇醚，甲硅烷基）的亲核性进行了比较乙烯酮缩醛）和碳负离子。结果表明，烯胺的亲核反应活性覆盖了十多个数量级，与低反应性末端的烯醇醚和高反应性末端的碳负离子相当。由于N攻击的产物在热力学上不如反应物稳定，因此观察到的速率常数是指碳键，碳键的形成。在某些情况下，
• Kinetics of the Friedel−Crafts Alkylations of Heterocyclic Arenes:  Comparison of the Nucleophilic Reactivities of Aromatic and Nonaromatic π-Systems
  作者：Matthias F. Gotta、Herbert Mayr

  DOI：10.1021/jo981373+

  日期：1998.12.1

  The kinetics of the reactions of benzhydryl cations with heteroarenes (N-methylpyrrole, furan, 2-methylfuran? and 2-methylthiophene) have been determined photometrically in dichloromethane, and the reaction products have been completely characterized by H-1 and C-13 NMR spectroscopy. The reactions follow second-order kinetics with rate-limiting formation of the sigma-adducts. The second-order rate constants correlate linearly with the electrophilicity parameter E of the benzhydryl cations. This allows the determination of the reactivity parameters N and s for the heteroarenes according to the linear free enthalpy relationship log k = s(E + N) (Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957). The nucleophilicity parameters N thus defined allow a direct comparison of the nucleophilic reactivities of aromatic and nonaromatic :pi-systems. Since N correlates linearly with sigma(arene)(+), it becomes possible to derive N parameters for arenes and heteroarenes with known sigma(+) parameters and to calculate absolute rate constants for their reactions with carbenium ions and diazonium ions. Applications of the reactivity parameters thus determined for the quantitative and qualitative prediction of the rates of electrophilic aromatic substitutions are discussed.
• Mayr, Herbert; Basso, Nils, Angewandte Chemie, 1992, vol. 104, # 8, p. 1103 - 1105
  作者：Mayr, Herbert、Basso, Nils

  DOI：——

  日期：——