α-(p-chlorobenzenesulfonyloxy)acetophenone | 110143-20-9

• 英文名称: α-(p-chlorobenzenesulfonyloxy)acetophenone
• 英文别名: α-(p-chlorophenylsulfonyloxy)acetophenone；phenacyl p-chlorobenzenesulphonate；Phenacyl 4-chlorobenzenesulfonate
• CAS: 110143-20-9
• 化学式: C₁₄H₁₁ClO₄S
• 分子量: 310.758
• InChiKey: QGKAHOBCGMUQIU-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C
• 沸点：
  466.6±30.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-(p-chlorobenzenesulfonyloxy)acetophenone 、 甲氧苯胺 以 甲醇 、 乙腈 为溶剂， 生成 2-((4-methoxyphenyl)amino)-1-phenylethanone
  参考文献：
  名称：

  Lee, Ikchoon; Shim, Chang Sub; Chung, Soo Young, Journal of the Chemical Society. Perkin transactions II, 1988, p. 975 - 982

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯磺酸 、 苯乙酮 在 碘苯 间氯过氧苯甲酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以78%的产率得到α-(p-chlorobenzenesulfonyloxy)acetophenone
  参考文献：
  名称：

  PHI-和酮和醇，以α-tosyloxyketones与聚合物负载的PHI-催化氧化转化米氯过苯甲酸和p -甲苯磺酸

  摘要：

  各种酮转化成相应的α-tosyloxyketones与米CPBA和p在碘苯催化量的存在对甲苯磺酸。此外，使用m CPBA和催化量的碘代苯和溴化钾将仲醇直接转化为相应的α-甲苯磺酰氧基酮，然后以对-甲苯磺酸的一锅法处理。聚（4-碘苯乙烯）也可用作与酮相同的α-甲苯磺酰化反应的可回收催化剂

  DOI：

  10.1016/j.tet.2007.03.091

文献信息

• 4-MeC6H4I-Mediated Efficient α-Tosyloxylation of Ketones with Oxone® and p-Toluenesulfonic Acid in Acetonitrile
  作者：Hideo Togo、Ayumi Tanaka

  DOI：10.1055/s-0029-1218370

  日期：2009.12

  Various alkyl aryl ketones, dialkyl ketones, and cycloheptanone were efficiently converted into the corresponding α-tosyl­oxy ketones in good yields by using Oxone® and p-toluenesulfonic acid monohydrate in the presence of p-iodotoluene in acetonitrile. 4-Methoxyacetophenone and 2-acetylthiophene bearing an electron-rich aromatic group could be also converted into the corresponding α-tosyloxyketones smoothly in good yields with the present method. Here, p-iodotoluene works as catalyst and p-[(hydroxy)(tosyloxy)]iodotoluene is formed in situ as a reactive species for the α-tosyloxylation of ketones. However, one equivalent of p-iodotoluene was required to obtain α-tosyloxyketones in good yields and was recovered in 80-20% yields, depending on the reaction conditions.

  通过在乙腈中使用Oxone®和p-甲苯磺酸一水合物，并在p-碘甲苯的存在下，各种烷基芳香酮、二烷基酮和环庚酮高效地转化为相应的α-甲苯磺酰氧基酮，产率良好。带有富电子芳香基团的4-甲氧基苯乙酮和2-乙酰基噻吩也可以用当前方法顺利地转化为相应的α-甲苯磺酰氧基酮，产率良好。在这里，p-碘甲苯作为催化剂，并且原位生成p-[(羟基)(甲苯磺酰氧基)]碘甲苯作为酮的α-甲苯磺酰氧化反应的活性物质。然而，为了获得良好的α-甲苯磺酰氧基酮产率，需要等量的p-碘甲苯，并且根据反应条件的不同，其回收率为80-20%。
• Novel α-tosyloxylation of ketones catalyzed by the in situ generated hypoiodous acid from alkyl iodide
  作者：Bijun Zhang、Liuquan Han、Jiantao Hu、Jie Yan

  DOI：10.1016/j.tetlet.2014.08.093

  日期：2014.10

  Using a catalytic amount of 1-iodopropane, a novel and efficient procedure has been developed for direct preparation of alpha-tosyloxyketones from ketones. In this protocol, 1-iodopropane is first oxidized into iodosylpropane, which decomposes to form the key catalyst hypoiodous acid. With this method, not only alpha-tosyloxyketones, but also other alpha-sulfonyloxyketones have been prepared in moderate to good yields, which extends the application of alkyl substituted hypervalent iodine reagents in organic synthesis. (C) 2014 Elsevier Ltd. All rights reserved.
• Group transfers. 1. Enolate structures contributing to the transition state for nucleophilic substitution on .alpha.-substituted carbonyl compounds
  作者：T. I. Yousaf、E. S. Lewis

  DOI：10.1021/ja00254a038

  日期：1987.9
• Effective<font>α</font>-Tosyloxylation of Ketones Using 1,1,1-Trifluoro-2-iodoethane as Catalyst
  作者：Bijun Zhang、Liuquan Han、Jiantao Hu、Jie Yan

  DOI：10.1080/00397911.2014.937500

  日期：2014.11.17

  With 1,1,1-trifluoro-2-iodoethane as catalyst, a novel and efficient procedure has been developed for preparation of alpha-tosyloxyketones from ketones. In this protocol, 1,1,1-trifluoro-2-iodoethane is first oxidized by m-chloroperbenzoic acid to a hypervalent iodine intermediate. The in situ-generated active iodine species then reacts with ketones to afford the corresponding alpha-tosyloxyketones in good yields.
• A Multiple Hammett Study of the Nucleophilic Substitution Reaction of ∝-Carbonyl Derivatives
  作者：Soo-Dong Yoh、Oh-Seuk Lee

  DOI：10.1016/s0040-4039(00)80514-6

  日期：1988.1