(2S)-2-[(4-methylbenzenesulfonyl)oxy]-1-phenylpropan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-[(4-methylbenzenesulfonyl)oxy]-1-phenylpropan-1-one
• 英文别名: (S)-1-oxo-1-phenylpropan-2-yl 4-methylbenzenesulfonate；1-oxo-1-phenylpropan-2-yl 4-methylbenzenesulfonate；[(2S)-1-oxo-1-phenylpropan-2-yl] 4-methylbenzenesulfonate
• 化学式: C₁₆H₁₆O₄S
• 分子量: 304.367
• InChiKey: AOXAGAXGWOAIHV-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 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：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-2-(甲苯-4-磺酰氧基)-丙酸 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 (2S)-2-[(4-methylbenzenesulfonyl)oxy]-1-phenylpropan-1-one
  参考文献：
  名称：

  Enantioselective α-tosyloxylation of ketones catalyzed by spirobiindane scaffold-based chiral iodoarenes

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2011.12.003

文献信息

• Isothiourea-Catalyzed Atroposelective N-Acylation of Sulfonamides
  作者：Jun-Yang Ong、Xiao Qian Ng、Shenci Lu、Yu Zhao

  DOI：10.1021/acs.orglett.0c02266

  日期：2020.8.21

  We report herein an atroposelective N-acylation of sulfonamides using a commercially available isothiourea catalyst, (S)-HBTM, with a simple procedure. The N-sulfonyl anilide products can be obtained in good to high enantiopurity, which represents a new axially chiral scaffold. The application of the product as a chiral iodine catalyst is also demonstrated for the asymmetric α-oxytosylation of propiophenone

  我们在此报道了使用市售异硫脲催化剂（S）-HBTM，以简单的程序进行的磺酰胺的对位选择性N-酰化。所述Ñ磺酰基酰苯胺产物可以良好地获得高对映体纯度，其代表一种新的轴向手性支架。还证明了该产物作为手性碘催化剂用于丙苯酮的不对称α-氧羰基化反应。
• 3,3′-Diiodobinaphthol and 3,3′-Diiodobiphenol Derivatives as Hypervalent Iodine Organocatalysts for the α-Oxytosylation of Ketones
  作者：Florian Berthiol、Simon Brenet、Clémentine Minozzi、Bastien Clarens、Lilia Amiri

  DOI：10.1055/s-0035-1560267

  日期：——

  of enantiopure 3,3′-diiodobinaphthol- and 3,3′-diiodobiphenol-based molecules have been synthesized and used as chiral hypervalent iodine oxidation organocatalysts in the α-oxytosylation of propiophenone. When we compared these new organocatalysts to our previous series of 3,3′-diiodo-1,1′-binaphthalene-2,2′-diol-fused maleimides, we have made two important observations: the maleimide moiety is the

  摘要 合成了一系列新的对映体纯的3,3'-二碘代二酚和3,3'-二碘代双酚基分子，并将其用作手性高价碘氧化有机催化剂，用于苯乙酮的α-氧合。当我们将这些新的有机催化剂与之前的3,3'-二碘-1,1'-联萘-2,2'-二醇稠合的马来酰亚胺系列进行比较时，我们得出了两个重要的观察结果：马来酰亚胺部分是获得适中的对映选择性，并且在催化剂的联芳基部分上存在脂肪族取代基会增强对映选择性。 合成了一系列新的对映体纯的3,3'-二碘代二酚和3,3'-二碘代双酚基分子，并将其用作手性高价碘氧化有机催化剂，用于苯乙酮的α-氧合。当我们将这些新的有机催化剂与之前的3,3'-二碘-1,1'-联萘-2,2'-二醇稠合的马来酰亚胺系列进行比较时，我们得出了两个重要的观察结果：马来酰亚胺部分是获得适中的对映选择性，并且在催化剂的联芳基部分上存在脂肪族取代基会增强对映选择性。
• Structurally Defined α-Tetralol-Based Chiral Hypervalent Iodine Reagents
  作者：Tobias Hokamp、Thomas Wirth

  DOI：10.1021/acs.joc.9b01315

  日期：2019.7.5

  A novel class of chiral hypervalent iodine reagents containing an α-tetralol scaffold is introduced. Iodine triacetate is employed in a key step as a highly selective and efficient iodinating reagent for a short and convenient synthesis of iodine(III) derivatives. Solid-state X-ray analyses offer valuable structural information, while reactivities and stereoselectivities are investigated in three model

  介绍了一种新型的含有α-四醇支架的手性高价碘试剂。三乙酸碘在关键步骤中用作高度选择性和高效的碘化试剂，可用于简短方便地合成碘（III）衍生物。固态X射线分析提供了有价值的结构信息，同时在三种模型反应中研究了反应性和立体选择性。
• Access to Axially and Centrally Chiral Sulfinamides via Asymmetric Allylic Alkylation
  作者：Gaoliang Zheng、Xin Li、Jin-Pei Cheng

  DOI：10.1021/acs.orglett.1c01201

  日期：2021.5.21

  Herein, access to axially and centrally chiral sulfinamides via asymmetric allylic alkylation was reported. A series of sulfinamides were obtained with good outcomes (up to 99% yield, >19:1 dr, and 98:2 er). The synthetic utility of the reaction was demonstrated by scaled-up synthesis, product transformation, and application as a catalyst in asymmetric catalysis.

  本文中，报道了通过不对称烯丙基烷基化获得轴向和中心手性亚磺酰胺。获得了一系列具有良好收率的亚磺酰胺（高达99％的收率，> 19：1 dr和98：2 er）。通过放大合成，产物转化以及在不对称催化中作为催化剂的应用证明了该反应的合成效用。
• Hypervalent Iodine(III)‐Catalysed Enantioselective α‐Acetoxylation of Ketones
  作者：Tobias Hokamp、Thomas Wirth

  DOI：10.1002/chem.202000927

  日期：2020.8.17

  An enantioselective catalytic synthesis of α‐acetoxylated ketones through I(I)/I(III) catalysis using a resorcinol/lactamide‐based chiral iodoarene is reported. Catalyst turnover by in situ generation of the active iodine(III) derivative is achieved by oxidation with mCPBA in the presence of acetic acid. The prior transformation of ketones to easily accessible acetyl enol ethers is beneficial and yields

  据报道，使用基于间苯二酚/乳酰胺的手性碘芳烃，通过 I(I)/I(III) 催化对映选择性催化合成 α-乙酰氧基化酮。通过在乙酸存在下用m CPBA氧化，原位生成活性碘 (III) 衍生物来实现催化剂周转。将酮预先转化为易于获得的乙酰烯醇醚是有益的，并且在温和的反应条件下仅使用仅 5 mol % 的低催化剂负载即可获得高达 97 % 的产率和高达 88 %  ee的对映选择性。