(+/-)-1-(4-chlorophenyl)-2-phenylethyl acetate | 92907-22-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+/-)-1-(4-chlorophenyl)-2-phenylethyl acetate
• 英文别名: 2-Phenyl-1-p-chlorphenyl-aethyl-acetat；[1-(4-Chlorophenyl)-2-phenylethyl] acetate
• CAS: 92907-22-7
• 化学式: C₁₆H₁₅ClO₂
• 分子量: 274.747
• InChiKey: WINYDTQMUQEHPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(4-chlorophenyl)-2-phenylethyl acetate 在 Pseudomonas cepacia lipase 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 290.0h， 生成 (R)-1-(4-chlorophenyl)-2-phenylethanol
  参考文献：
  名称：

  Asymmetric preparation of antifungal 1-(4′-chlorophenyl)-1-cyclopropyl methanol and 1-(4′-chlorophenyl)-2-phenylethanol. Study of the detoxification mechanism by Botrytis cinerea

  摘要：

  Chiral alcohols are important as bioactive compounds or as precursors to such molecules. On the basis of the different antifungal properties of the enantiopure alcohol derivatives of 4'-chlorophenyl cyclopropyl ketone and benzyl 4'-chlorophenyl ketone, their enantioselective synthesis by chemical and biocatalytic methods was studied. The detoxification pathways by the phytopathogen fungus Bonytis cinerea are reported. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.02.005
• 作为产物：
  描述：

  4-氯苯基苄基酮 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 (+/-)-1-(4-chlorophenyl)-2-phenylethyl acetate
  参考文献：
  名称：

  Asymmetric preparation of antifungal 1-(4′-chlorophenyl)-1-cyclopropyl methanol and 1-(4′-chlorophenyl)-2-phenylethanol. Study of the detoxification mechanism by Botrytis cinerea

  摘要：

  Chiral alcohols are important as bioactive compounds or as precursors to such molecules. On the basis of the different antifungal properties of the enantiopure alcohol derivatives of 4'-chlorophenyl cyclopropyl ketone and benzyl 4'-chlorophenyl ketone, their enantioselective synthesis by chemical and biocatalytic methods was studied. The detoxification pathways by the phytopathogen fungus Bonytis cinerea are reported. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.02.005

文献信息

• Substituent Effect Studies of Aryl-Assisted Solvolyses. II. The Acetolysis of 2-Phenyl-2-(substituted phenyl)ethyl<i>p</i>-Toluenesulfonates
  作者：Mizue Fujio、Yasuyuki Maeda、Mutsuo Goto、Yoshihiro Saeki、Masaaki Mishima、Yuho Tsuno

  DOI：10.1246/bcsj.66.3021

  日期：1993.10

  The substituent effect on the acetolysis of 2-phenyl-2-(substituted phenyl)ethyl p-toluenesulfonates had a nonlinear LArSR correlation and was explicable in terms of a competitive aryl-assisted mechanism involving the X-substituted phenyl-assisted () pathway and the unsubstituted phenyl-assisted () pathway. By the application of the iterative nonlinear least-squares method based on the LArSR Eq., the

  取代基对 2-苯基-2-（取代苯基）乙基对甲苯磺酸酯的乙酰化作用具有非线性 LArSR 相关性，并且可以根据涉及 X 取代苯基辅助 () 途径的竞争性芳基辅助机制进行解释。未取代的苯基辅助 () 途径。通过应用基于 LArSR 方程的迭代非线性最小二乘法，将取代基对整体 kt 的影响分解为 ρM = -3.53 和 rM = 0.60 的最佳拟合 kM 相关性，以及 ρN 的 kN 相关性= -0.88 σ0。辅助芳基取代基效应的 ρM 和 rM 值非常接近于 2-甲基-2-苯丙基体系的值，并且辅助芳基的小 ρN 值与未升高的 σ0 常数与远程 β-芳基效应相容。基于取代基效应分析分析的竞争途径的相对速率与通过 13C-示踪法确定的各个芳基迁移产物的比例完全一致。精确的 ...