苯甲酰基苯磺酸盐 | 98475-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苯甲酰基苯磺酸盐
• 英文名称: α-phenylsulfonyloxyacetophenone
• 英文别名: phenacyl benzenesulphonate；phenacyl benzenesulfonate；2-Oxo-2-phenylethyl benzenesulfonate
• CAS: 98475-06-0
• 化学式: C₁₄H₁₂O₄S
• 分子量: 276.313
• InChiKey: LVJABPYBQCMMML-UHFFFAOYSA-N

物化性质

• 沸点：
  444.7±28.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  苯甲酰基苯磺酸盐 、 乙烷,三氯氟- 以 甲醇 、 乙腈 为溶剂， 生成 N-phenacyl-p-toluidine
  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：

  苯乙酮 、 苯磺酸 在 1-碘代丙烷 、 间氯过氧苯甲酸 作用下， 以 2,2,2-三氟乙醇 、 乙腈 为溶剂， 反应 8.0h， 以65%的产率得到苯甲酰基苯磺酸盐
  参考文献：
  名称：

  Novel α-tosyloxylation of ketones catalyzed by the in situ generated hypoiodous acid from alkyl iodide

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2014.08.093

文献信息

• Synthesis of α-sulfonyloxyketones <i>via</i> iodobenzene diacetate (PIDA)-mediated oxysulfonyloxylation of alkynes with sulfonic acids
  作者：Yang Zhang、Hua Tan、Weibing Liu

  DOI：10.1039/c7ra11875a

  日期：——

  A simple yet powerful method to synthesize a variety of α-sulfonyloxyketones has been developed. This novel method can be applied for the direct oxysulfonyloxylation of alkynes with sulfonic acids to access a variety of α-sulfonyloxyketones. Compared to the reported methods for the application of PIDA, this study expands its application scope and uses it not only as the oxidant but also as the carrier

  已经开发了一种简单而有效的合成多种α-磺酰氧基酮的方法。这种新方法可用于炔烃与磺酸的直接氧磺酰氧基化反应，从而获得各种α-磺酰氧基酮。与报道的PIDA的应用方法相比，本研究扩大了其应用范围，不仅将其用作氧化剂，而且还用作“ O”的载体在产品中形成羰基。另外，在确定的条件下，该方法不仅显示出较宽的底物范围，而且还证明了与1,2-二取代内部炔烃的底物具有独特的区域选择性。
• Sulfonic acids, their derivatives and pharmaceutical compositions containing them
  申请人：Dompé S.P.A.

  公开号：EP1457485A1

  公开（公告）日：2004-09-15

  Selected sulfonic acids, their derivatives and pharmaceutical compositions containing such compounds are useful in inhibiting the chemotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCR1 and CXCR2 membrane receptors. The compounds are used for the prevention and treatment of pathologies deriving from said activation. Notably, the selected sulfonic acids and their derivativas are devoid of cyclo-oxygenase inhibition activity and are particularly useful in the treatment of neutrofil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD), bullous pemphigoid, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.

  选择性磺酸、它们的衍生物和含有这些化合物的药物组合物在抑制由白细胞介素-8（IL-8）与CXCR1和CXCR2膜受体相互作用引起的中性粒细胞（PMN白细胞）趋化活化方面是有用的。这些化合物用于预防和治疗由该活化引起的病理状况。值得注意的是，所选的磺酸及其衍生物不具有环氧化酶抑制活性，特别适用于治疗中性粒细胞依赖性病理状况，如银屑病、溃疡性结肠炎、黑色素瘤、慢性阻塞性肺疾病（COPD）、大疱性类天疱疮、类风湿性关节炎、特发性纤维化、肾小球肾炎以及预防和治疗缺血再灌注引起的损伤。
• Kinetic studies for the reactions of phenacyl p-bromobenzenesulfonate with substituted pyridines under high pressures
  作者：Soo-Dong Yoh、Kyung-Hwan Park、Sung-Hong Kim、Duk-Young Cheong

  DOI：10.1016/s0040-4020(01)81011-5

  日期：1989.1

  Kinetic studies of the reactions of phenacyl p-bromobenzenesulfonate(brosylate) with substituted pyridines at 1–1500 atm and 35, 45, and 55°C in acetonitrile were carried out by electric conductivity method. From the activation volumes and activation entropies, it can be deduced that phenacyl brosylate has SN2 character in the transition state like other Menschutkin reactions of benzyl benzenesulfonate

  通过电导率法研究了苯甲酰基对溴苯磺酸盐（溴甲酸酯）与取代的吡啶在1–1500 atm以及35、45和55°C下在乙腈中的反应。从活化体积和活化熵可以推断出，苯甲酰基溴磺酸盐在过渡态具有S N 2特征，就像苄基苯磺酸盐，2-苯乙基芳磺酸盐，乙基碘和十六烷基溴化物与吡啶的其他Menschutkin反应一样。升高压力后，哈米特| ϱ | Br？nstedβ值增加表明该反应随压力增加而具有增加的S N 2特性。
• 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.