1-(3-(trifluoromethyl)phenyl)-1-oxopropan-2-yl 4-methylbenzenesulfonate | 936632-17-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-(trifluoromethyl)phenyl)-1-oxopropan-2-yl 4-methylbenzenesulfonate
• 英文别名: [(2R)-1-oxo-1-[3-(trifluoromethyl)phenyl]propan-2-yl] 4-methylbenzenesulfonate
• CAS: 936632-17-6
• 化学式: C₁₇H₁₅F₃O₄S
• 分子量: 372.365
• InChiKey: TUACGHPBMAXRKT-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  间三氟甲基苯丙酮 在 正丁基锂 、 (2R,2'R)-2,2'-((2-iodo-1,3-phenylene)bis(oxy))bis(N-methyl-N-phenylpropanamide) 、 二异丙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 25.75h， 生成 1-(3-(trifluoromethyl)phenyl)-1-oxopropan-2-yl 4-methylbenzenesulfonate 、 1-oxo-1-(3-(trifluoromethyl)phenyl)propan-2-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  对映选择性碘（III）介导的α-甲苯磺酰基酮的合成：打破了选择性壁垒。

  摘要：

  由于其无处不在的性质，开发接近手性非外消旋α-取代酮的实用方法尤为重要。报告了使用烯醇酯和手性碘（III）试剂合成α-甲苯磺酰氧基酮的前所未有的对映选择性水平。该反应可以在化学计量和催化条件下进行。这些结果表明酮与烯醇酯反应的反应机理大不相同，这支持了最新的计算见解。

  DOI：

  10.1021/acs.orglett.5b02501

文献信息

• Asymmetric α-Sulfonyl- and α-Phosphoryl-Oxylation of Ketones by a Chiral Hypervalent Iodine(III)
  作者：Guillaume Levitre、Audrey Dumoulin、Pascal Retailleau、Armen Panossian、Frédéric R. Leroux、Géraldine Masson

  DOI：10.1021/acs.joc.7b01597

  日期：2017.11.17

  An enantioselective direct oxygenation of propiophenone derivatives mediated by a catalytic or stoichiometric amount of new chiral non-C2-symmetric iodoarenes(III) is reported. The reaction gives an easy entry to optically active α-sulfonyl- and α-phosphoryl oxyketones in respectable yields and enantioselectivities.

  据报道，由催化或化学计量的新手性非C 2对称碘代芳烃（III）介导的对苯乙酮衍生物的对映选择性直接氧化。该反应使光学活性的α-磺酰基-和α-磷酰基氧基酮易于以可观的收率和对映选择性进入。
• Catalytic Enantioselective α-Oxysulfonylation of Ketones Mediated by Iodoarenes
  作者：Sabine M. Altermann、Robert D. Richardson、T. Keri Page、Ruth K. Schmidt、Edward Holland、Umal Mohammed、Shauna M. Paradine、Andrew N. French、Christine Richter、A. Masih Bahar、Bernhard Witulski、Thomas Wirth

  DOI：10.1002/ejoc.200800741

  日期：2008.11

  alpha-oxysulfonylation of ketones catalysed by enantioenriched iodoarenes using mCPBA as stoichiometric oxidant is reported to give useful synthetic intermediates in good yield and modest enantioselectivity. We believe this to be the first report of an enantioselective organocatalytic reaction involving hypervalent iodine reagents which should open up a new field for enantioselective organocatalysis of oxidation

  据报道，使用 mCPBA 作为化学计量氧化剂，由富含对映体的碘芳烃催化的酮的 α-氧磺酰化以良好的产率和适度的对映选择性得到有用的合成中间体。我们相信这是涉及高价碘试剂的对映选择性有机催化反应的第一份报告，这将为氧化反应的对映选择性有机催化开辟一个新领域。
• C−N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α‐Oxytosylation of Ketones
  作者：Haifa Alharbi、Mohamed Elsherbini、Jihan Qurban、Thomas Wirth

  DOI：10.1002/chem.202005253

  日期：2021.3

  A simple synthesis of a library of novel C−N axially chiral iodoarenes is achieved in a three‐step synthesis from commercially available aniline derivatives. C−N axial chiral iodine reagents are rarely investigated in the hypervalent iodine arena. The potential of the novel chiral iodoarenes as organocatalysts for stereoselective oxidative transformations is assessed using the well explored, but challenging

  从市场上可买到的苯胺衍生物的三步合成中，可以轻松合成新颖的CN轴向手性碘代芳烃库。在高价碘领域中很少研究C–N轴向手性碘试剂。新型手性碘代芳烃作为有机催化剂进行立体选择性氧化转化的潜力已通过深入研究但具有挑战性的酮的立体选择性α-氧羰基化反应进行了评估。所有研究的试剂均具有良好的立体化学控制，可将苯乙酮立体选择性氧化为相应的手性α-氧羰基化产品。使用优化的反应条件，通常以良好的收率获得优异的收率，并且具有良好的对映选择性。
• Enantioselective α-tosyloxylation of ketones catalyzed by spirobiindane scaffold-based chiral iodoarenes
  作者：Jun Yu、Jian Cui、Xue-Sen Hou、Shan-Shan Liu、Wen-Chao Gao、Shan Jiang、Jun Tian、Chi Zhang

  DOI：10.1016/j.tetasy.2011.12.003

  日期：2011.12

  Enantiomerically pure iodoarene (S)-2 and its derivatives (S)-3 to (S)-18 with a spirobiindane scaffold have been synthesized. The evaluation of these new chiral iodoarenes as catalysts in the enantioselective alpha-tosyloxylation of ketones was performed using m-CPBA as a stoichiometric oxidant, and the synthetically useful alpha-tosyloxylated ketones were obtained in up to 58% enantiomeric excess (ee). (C) 2011 Elsevier Ltd. All rights reserved.
• Catalytic Enantioselective α-Tosyloxylation of Ketones Using Iodoaryloxazoline Catalysts: Insights on the Stereoinduction Process
  作者：Audrey-Anne Guilbault、Benoit Basdevant、Vincent Wanie、Claude Y. Legault

  DOI：10.1021/jo302393u

  日期：2012.12.21

  A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The alpha-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.