3-tosyloxy-2-octanone

• 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: 3-tosyloxy-2-octanone
• 英文别名: 2-Oxooctan-3-yl 4-methylbenzenesulfonate；2-oxooctan-3-yl 4-methylbenzenesulfonate
• 化学式: C₁₅H₂₂O₄S
• 分子量: 298.403
• InChiKey: UPKRGQVYMUTEGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲苯磺酸 、 仲辛酮 在 碘苯 间氯过氧苯甲酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以66%的产率得到3-tosyloxy-2-octanone
  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

• PhI- and polymer-supported PhI-catalyzed oxidative conversion of ketones and alcohols to α-tosyloxyketones with m-chloroperbenzoic acid and p-toluenesulfonic acid
  作者：Yukiharu Yamamoto、Yuhta Kawano、Patrick H. Toy、Hideo Togo

  DOI：10.1016/j.tet.2007.03.091

  日期：2007.5

  Various ketones were converted to the corresponding α-tosyloxyketones with mCPBA and p-toluenesulfonic acid in the presence of a catalytic amount of iodobenzene. Moreover, secondary alcohols were directly converted to the corresponding α-tosyloxyketones using mCPBA and catalytic amounts of iodobenzene and potassium bromide, followed by treatment with p-toluenesulfonic acid in a one-pot manner. Poly(4-iodostyrene)

  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
• 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%。
• Iodoarene-Mediated α-Tosyloxylation of Ketones with MCPBA and p-Toluenesulfonic Acid
  作者：Hideo Togo、Ayumi Tanaka、Katsuhiko Moriyama

  DOI：10.1055/s-0030-1260948

  日期：2011.8

  Alkyl aryl ketones and dialkyl ketones could be converted into the corresponding α-tosyloxy ketones by the reaction with MCPBA and p-toluenesulfonic acid monohydrate (PTSA˙H2O) in the presence of a catalytic amount of molecular iodine (I2) in a mixture of acetonitrile and 2,2,2-trifluoroethanol, although the yields were dependent on the ketones (method A). The same conversion of alkyl aryl ketones and dialkyl ketones into the corresponding α-­tosyloxy ketones could be smoothly carried out by the reaction with MCPBA and PTSA˙H2O in the presence of catalytic amounts of ­iodine and tert-butylbenzene in a mixture of acetonitrile and 2,2,2-trifluoroethanol (method B). In those reactions, p-iodotoluene and 4-tert-butyl-1-iodobenzene were formed at first in method A and method B, respectively, and then they were converted into p-[(hydroxy)(tosyloxy)]iodotoluene and 4-tert-butyl-1-[(hydroxy)(tosyloxy)iodo]benzene by the reaction with MCPBA and PTSA˙H2O. p-[(Hydroxy)(tosyloxy)]iodotoluene and 4-tert-butyl-1-[(hydroxy)-(tosyloxy)iodo]benzene worked as an α-tosyloxylation reagent of ketones.

  烷基芳基酮和二烷基酮可以通过与间氯过氧苯甲酸（MCPBA）和单水合对甲苯磺酸（PTSA·H2O）在催化量的碘分子（I2）存在下反应，在乙腈和2,2,2-三氟乙醇的混合物中，转化为相应的α-甲苯磺酰氧基酮，尽管产率取决于酮类（方法A）。烷基芳基酮和二烷基酮同样可以通过与MCPBA和PTSA·H2O在催化量的碘和叔丁基苯存在下反应，在乙腈和2,2,2-三氟乙醇的混合物中，顺利转化为相应的α-甲苯磺酰氧基酮（方法B）。在这些反应中，方法A和方法B分别首先形成对碘甲苯和4-叔丁基-1-碘苯，然后它们通过与MCPBA和PTSA·H2O反应转化为对[(羟基)(甲苯磺酰氧基)]碘甲苯和4-叔丁基-1-[(羟基)(甲苯磺酰氧基)碘]苯。对[(羟基)(甲苯磺酰氧基)]碘甲苯和4-叔丁基-1-[(羟基)(甲苯磺酰氧基)碘]苯作为酮的α-甲苯磺酰氧化试剂。