N-Methyl-trifluoracetyl-p-chlor-anilin | 32368-26-6

• 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: N-Methyl-trifluoracetyl-p-chlor-anilin
• 英文别名: N-(4-chlorophenyl)-2,2,2-trifluoro-N-methylacetamide
• CAS: 32368-26-6
• 化学式: C₉H₇ClF₃NO
• 分子量: 237.609
• InChiKey: HONPEOFVZVYICO-UHFFFAOYSA-N

物化性质

• 沸点：
  236.9±40.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Methyl-trifluoracetyl-p-chlor-anilin 在 β-环糊精 水 作用下， 以 乙腈 为溶剂， 生成 4-氯-N-甲基苯胺
  参考文献：
  名称：

  Re-Evaluation of Cyclodextrin as a Model of Chymotrypsin: Acceleration and Inhibition of Tertiary Anilide Hydrolysis

  摘要：

  The hydrolysis of p-nitro-N-methyltrifluoroacetanilide (1), p-chloro-N-methyltrinuoroacetanilide (2), N-methyltrifluoroacetanilide (3), and p-methoxy-N-methyltrifluoroacetanilide (4) in the presence and absence of alpha- and beta-cyclodextrin has been studied at 7.5 < pH < 10.6. For 1-3, cyclodextrin (CD) exhibits simple Michaelis-Menten saturation kinetics, with no evidence for reaction via other than 1:1 CD-substrate complexes. The behavior of CD with 4 is more complex. Moreover, CD catalyzes the hydrolysis of 1 but inhibits the hydrolysis of 2-4 across the pH range studied. The nature of the buffer catalysis in the absence of CD, exhibited in the hydrolysis of 1, also shows marked differences with that exhibited by 2-4. The data are most simply interpreted by a mechanism in which CD accelerates formation of a tetrahedral intermediate 5; in the case of 1, the rate of breakdown of this intermediate is greater than the rate of buffer-catalyzed breakdown of the hydrolysis intermediate. The CD cavity may provide an environment complementary to the transition state for expulsion of the anilide leaving group. These results are compared with the previously reported effects of CDs on trifluoroacetanilide and phenyl ester hydrolysis and proposals of CD as a model of chymotrypsin.

  DOI：

  10.1021/jo00097a034
• 作为产物：
  描述：

  4-氯-N-甲基苯胺 、 三氟乙酸酐 以 四氢呋喃 为溶剂， 生成 N-Methyl-trifluoracetyl-p-chlor-anilin
  参考文献：
  名称：

  Re-Evaluation of Cyclodextrin as a Model of Chymotrypsin: Acceleration and Inhibition of Tertiary Anilide Hydrolysis

  摘要：

  The hydrolysis of p-nitro-N-methyltrifluoroacetanilide (1), p-chloro-N-methyltrinuoroacetanilide (2), N-methyltrifluoroacetanilide (3), and p-methoxy-N-methyltrifluoroacetanilide (4) in the presence and absence of alpha- and beta-cyclodextrin has been studied at 7.5 < pH < 10.6. For 1-3, cyclodextrin (CD) exhibits simple Michaelis-Menten saturation kinetics, with no evidence for reaction via other than 1:1 CD-substrate complexes. The behavior of CD with 4 is more complex. Moreover, CD catalyzes the hydrolysis of 1 but inhibits the hydrolysis of 2-4 across the pH range studied. The nature of the buffer catalysis in the absence of CD, exhibited in the hydrolysis of 1, also shows marked differences with that exhibited by 2-4. The data are most simply interpreted by a mechanism in which CD accelerates formation of a tetrahedral intermediate 5; in the case of 1, the rate of breakdown of this intermediate is greater than the rate of buffer-catalyzed breakdown of the hydrolysis intermediate. The CD cavity may provide an environment complementary to the transition state for expulsion of the anilide leaving group. These results are compared with the previously reported effects of CDs on trifluoroacetanilide and phenyl ester hydrolysis and proposals of CD as a model of chymotrypsin.

  DOI：

  10.1021/jo00097a034

文献信息

• Re-Evaluation of Cyclodextrin as a Model of Chymotrypsin: Acceleration and Inhibition of Tertiary Anilide Hydrolysis
  作者：David R. J. Palmer、Erwin Buncel、Gregory R. J. Thatcher

  DOI：10.1021/jo00097a034

  日期：1994.9

  The hydrolysis of p-nitro-N-methyltrifluoroacetanilide (1), p-chloro-N-methyltrinuoroacetanilide (2), N-methyltrifluoroacetanilide (3), and p-methoxy-N-methyltrifluoroacetanilide (4) in the presence and absence of alpha- and beta-cyclodextrin has been studied at 7.5 < pH < 10.6. For 1-3, cyclodextrin (CD) exhibits simple Michaelis-Menten saturation kinetics, with no evidence for reaction via other than 1:1 CD-substrate complexes. The behavior of CD with 4 is more complex. Moreover, CD catalyzes the hydrolysis of 1 but inhibits the hydrolysis of 2-4 across the pH range studied. The nature of the buffer catalysis in the absence of CD, exhibited in the hydrolysis of 1, also shows marked differences with that exhibited by 2-4. The data are most simply interpreted by a mechanism in which CD accelerates formation of a tetrahedral intermediate 5; in the case of 1, the rate of breakdown of this intermediate is greater than the rate of buffer-catalyzed breakdown of the hydrolysis intermediate. The CD cavity may provide an environment complementary to the transition state for expulsion of the anilide leaving group. These results are compared with the previously reported effects of CDs on trifluoroacetanilide and phenyl ester hydrolysis and proposals of CD as a model of chymotrypsin.