(R,S)-4-(4-chlorophenyl)-2-[(2-hydroxyethyl)sulfanyl]-4-oxo-N-phenylbutanamide | 1470025-04-7

• 英文名称: (R,S)-4-(4-chlorophenyl)-2-[(2-hydroxyethyl)sulfanyl]-4-oxo-N-phenylbutanamide
• 英文别名: 4-(4-chlorophenyl)-2-(2-hydroxyethylsulfanyl)-4-oxo-N-phenylbutanamide
• CAS: 1470025-04-7
• 化学式: C₁₈H₁₈ClNO₃S
• 分子量: 363.865
• InChiKey: BPXLKNWRMCZOAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2E)-4-(4-chlorophenyl)-4-oxo-N-phenyl-2-butenamide 、 2-巯基乙醇 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到(R,S)-4-(4-chlorophenyl)-2-[(2-hydroxyethyl)sulfanyl]-4-oxo-N-phenylbutanamide
  参考文献：
  名称：

  Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study

  摘要：

  The reactivity of fifteen (E)-4-aryl-4-oxo-2-butenoic (aroylacrylic) acid arylamides toward thiols was studied, measuring the rate constants of the addition of model thiol nucleophile, 2-mercaptoethanol. The influence of the variation of the substituents on the phenyl rings on the rate of reaction was quantified using the Hammett substituent constants and descriptors derived from ab initio or semiempirical calculations (atomic charges, HOMO, and LUMO). Statistically significant linear correlations between second-order rate constants and Hammett substituent constants, as well as energies of LUMO orbitals, were obtained. Substituents on both aroyl and arylamido moieties were shown to influence the reactivity of studied compounds toward thiols. The regioselectivity of reaction was confirmed by NMR spectroscopy. Exclusively beta-addition product with respect to the aroyl keto group was obtained. The determined enthalpy and entropy of activation were found to be in agreement with the proposed reaction mechanism, which includes a highly ordered transition state.

  DOI：

  10.1007/s00706-013-1084-6