(tosyloxy)methyl 2-furanyl ketone | 80521-10-4

• 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: (tosyloxy)methyl 2-furanyl ketone
• 英文别名: [2-(Furan-2-yl)-2-oxoethyl] 4-methylbenzenesulfonate
• CAS: 80521-10-4
• 化学式: C₁₃H₁₂O₅S
• 分子量: 280.301
• InChiKey: AFQSJCWVLQSYBU-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64 °C
• 沸点：
  457.4±30.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (tosyloxy)methyl 2-furanyl ketone 在 甲酸 、 Cp*RhCl[(S,S)-TsDPEN] 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以98%的产率得到(S)-2-(furan-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Enantioselective Rh-catalyzed transfer hydrogenation of α-sulfonyloxy heteroaryl ketones; asymmetric synthesis of (S)-bufuralol

  摘要：

  Asymmetric transfer hydrogenation of a-sulfonyloxy heteroaryl ketones mediated by Cp*RhCl[(S,S)-TsDPEN] using an azeotropic mixture of formic acid/triethylamine afforded the corresponding diol-2-monosulfonates in excellent yield with high enantioselectivity. This led to the asymmetric synthesis of (S)-bufuralol. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.002
• 作为产物：
  描述：

  2-乙酰基呋喃 、 对甲苯磺酸 在 potassium peroxymonosulfate 、 4-碘甲苯 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以45%的产率得到(tosyloxy)methyl 2-furanyl ketone
  参考文献：
  名称：

  4-MeC6H4I-Mediated Efficient α-Tosyloxylation of Ketones with Oxone® and p-Toluenesulfonic Acid in Acetonitrile

  摘要：

  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%。

  DOI：

  10.1055/s-0029-1218370

文献信息

• Iodobenzene-Catalyzed Synthesis of α-Azidoketones and α-Thiocyanatoketones from Aryl Ketones with MCPBA as a Cooxidant
  作者：Ya-Li Chang、Chi-Lin Chung、Fang-Wen Wu、Huey-Min Wang、Rei-Sheu Hou、Iou-Jiun Kang、Ling-Ching Chen

  DOI：10.1002/jccs.201000023

  日期：2010.4

  Iodobenzene‐catalyzed synthesis of α‐azidoketones and α‐thiocyanatoketones from aryl ketones with MCPBA as a cooxidant is described. The method is simple, rapid and practical, generating α‐azidoketones and α‐thiocyanatoketones from the aryl ketone without isolation of α‐tosyloxyketones in good to excellent yields.

  描述了碘化苯催化MCPBA作为助氧化剂由芳基酮合成α-叠氮酮和α-硫氰基酮的方法。该方法简单，快速且实用，可从芳基酮生成α-叠氮酮和α-硫氰基酮，而无需分离α-甲苯磺酰氧基酮，收率好至极好。
• A New Application of Hypervalent Iodine (λ⁵) Reagents with Organosulfonic Acids for Direct α-Organosulfonyloxylation Carbonyl Compounds
  作者：Krishnacharya Akamanchi、Ulhas Mahajan

  DOI：10.1055/s-2008-1072508

  日期：——

  Hypervalent iodine (λ 5 ) reagents in combination with P-toluenesulfonic acid when reacted with ketones under reflux temperature in acetonitrile gave α-tosyloxy ketones in moderate to excellent yields. The reaction was developed further for both ketones and dicarbonyl compounds using Dess-Martin periodinane reagent in combination with P-toluenesulfonic acid and methanesulfonic acid, to give mono-α-tosyloxy

  当在回流温度下在乙腈中与酮反应时，高价碘 (λ 5 ) 试剂与对甲苯磺酸结合，以中等至极好的收率得到 α-甲苯磺酰氧基酮。使用 Dess-Martin 高碘烷试剂与对甲苯磺酸和甲磺酸结合，进一步开发了酮和二羰基化合物的反应，以非常高的收率得到单-α-甲苯磺酰氧基和单-α-甲磺酰氧基产物。
• 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。
• Iodobenzene-Catalyzed Synthesis of Imidazo[1,2-a]pyridines from Aryl Ketones with mCPBA in Ionic Liquid
  作者：Ya-Li Chang、Huey-Min Wang、Rei-Sheu Hou、Iou-Jiun Kang、Ling-Ching Chen

  DOI：10.1002/jccs.201000024

  日期：2010.4

  Iodobenzene‐catalyzed synthesis of imidazo[1,2‐a]pyridines from aryl ketones with mCPBA as a cooxidant in ionic liquid is described. The method is simple, rapid and practical, generating Imidazo[1,2‐a]pyridines from the aryl ketone without isolation of α‐tosyloxyketones in good to excellent yields.

  描述了碘代苯在离子液体中以mCPBA为助氧化剂从芳基酮催化合成咪唑并[1,2- a ]吡啶。该方法简单，快速且实用，可从芳基酮生成咪唑并[1,2- a ]吡啶，而无需分离α-甲苯磺酰氧基酮，产率高至优异。
• An Iodobenzene-Catalysed Domino Route toward Quinoxaline Derivatives from Simple Ketones and<i>o</i>-Phenylenediamines in One Pot
  作者：Xiaoqing Li、Can Zhou、Zhiyan Hu、Xiangsheng Xu

  DOI：10.3184/174751913x13758803237636

  日期：2013.9

  An iodobenzene-catalysed domino route to quinoxalines from ketones and o-phenylenediamines in one pot has been developed. This transformation consisted of the generation of Koser's generation, α-tosyloxylation of ketones, nucleophilic substitution and intramolecular dehydration with o-phenylenediamines, and dehydrogenation.

  研究人员开发出了一种碘苯催化的多米诺路线，可在一锅内从酮和邻苯二胺制备出喹喔啉类化合物。这一转化过程包括科塞生成、酮的α-甲苯基氧基化、邻苯二胺的亲核取代和分子内脱水以及脱氢。