2-羟基-5-(对甲苯磺酰氧基)苯甲酸甲酯 | 94033-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-5-(对甲苯磺酰氧基)苯甲酸甲酯
• 英文名称: methyl 2-hydroxy-5-(p-tolylsulphonyloxy)benzoate
• 英文别名: methyl 2-hydroxy-5-(tosyloxy)benzoate；2-methoxyformyl-4-tosyloxyphenol；2-carbomethoxy-4-tosyloxyphenol；methyl 2-hydroxy-5-{[(4-methylphenyl)sulfonyl]oxy}benzoate；methyl 2-hydroxy-5-(4-methylphenyl)sulfonyloxybenzoate
• CAS: 94033-94-0
• 化学式: C₁₅H₁₄O₆S
• 分子量: 322.339
• InChiKey: IHIDHZXSOHCTQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-羟基-5-(对甲苯磺酰氧基)苯甲酸甲酯 在 甲酸 、 水 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 5-({[(2R)-1-methyI-2-pyrrolidinyl]methyl}oxy)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS
  [FR] COMPOSÉS INÉDITS

  摘要：

  本发明公开了抑制LRRK2激酶活性的新化合物，其制备过程，含有它们的组合物，以及在治疗以LRRK2激酶活性为特征的疾病中的应用，特别是帕金森病和阿尔茨海默病。

  公开号：

  WO2011038572A1
• 作为产物：
  描述：

  2,5-二羟基苯甲酸甲酯 在 TEA 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.33h， 生成 2-羟基-5-(对甲苯磺酰氧基)苯甲酸甲酯
  参考文献：
  名称：

  The regioselective cleavage of aryl tosylates by electrochemical reduction

  摘要：

  The electrochemical reductions of eight bis(tosyloxy)benzanoid compounds were studied as a method for the regioselective cleavage of aryl tosylates. For the methyl bis(tosyloxy)benzoate isomers, a strong preference was observed for cleavage of the tosyl group in conjugation with the electron-withdrawing ester moiety. Thus it was possible to selectively cleave tosyl groups to the ortho or para positions over tosyl groups at the meta positions. The bis(tosyloxy)anisole isomers displayed the opposite regioselectivity favoring cleavage of tosyl groups that were meta to the electron-donating methoxy substituent. The general electrochemical process for the reduction of aryl tosylates has been shown to be selective, high yielding, and reproducible on gram quantities.

  DOI：

  10.1021/jo00029a010

文献信息

• Efficient Synthesis of Various 4-Tosyloxy-2-substituted Phenols Using Pyridinium Salt-supported [Hydroxy(tosyloxy)iodo]benzene Reagent
  作者：Bing Yang、Jizhen Zhang、Dejian Zhao、Yazhen Wang、Hongbin Jia

  DOI：10.1246/cl.130229

  日期：2013.8.5

  A novel pyridinium salt-supported [hydroxy(tosyloxy)iodo]benzene (HTIB) reagent (N-4-[hydroxy(tosyloxy)iodo]phenyl}pyridinium hexafluorophosphate) was prepared via Zincke’s reaction. The conjugate...

  通过 Zincke 反应制备了新型吡啶鎓盐负载的 [羟基（甲苯磺酰氧基）碘] 苯 (HTIB) 试剂（N-4-[羟基（甲苯磺酰氧基）碘]苯基}吡啶鎓六氟磷酸盐）。共轭...
• The Synthesis of 4-Tosyloxy-2-Substituted Phenols using New Solid Pyridinium Salt Supported [Hydroxyl(Tosyloxy)Iodo]Benzene Reagents
  作者：Bing Yang、Jizhen Zhang、Dejian Zhao、Hua Kuang

  DOI：10.3184/174751912x13338131755814

  日期：2012.5

  Two new solid pyridinium salt supported HTIB reagents (N-4-[hydroxyl(tosyloxy)iodo]benzyl}pyridinium tetrafluoroborate and N-4-[hydroxyl(tosyloxy)iodo]phenylcarbamoylmethyl}pyridinium tetrafluoroborate) were synthesised using a pyridinium salt as a cationic support. Although the former was hygroscopic the latter was stable in air and in a highly humid atmosphere over a few weeks. The latter has an

  使用吡啶鎓盐合成了两种新的固体吡啶鎓盐负载 HTIB 试剂（N-4-[羟基（甲苯磺酰氧基）碘]苄基}四氟硼酸吡啶鎓和 N-4-[羟基（甲苯磺酰氧基）碘]苯基氨基甲酰基甲基}吡啶鎓四氟硼酸盐）阳离子载体。尽管前者具有吸湿性，但后者在空气中和高度潮湿的大气中稳定了数周。后者有一个额外的酰胺键。两种化合物的结构均通过IR、1H NMR、13C NMR、MS和元素分析确定。然后，使用新试剂成功制备了两种 4-tosyloxy-2-取代苯酚。两种试剂都很容易以高产率再生。
• A novel and convenient approach for tosyloxylation of aromatic ring of some ortho-substituted phenolic compounds using [hydroxy(tosyloxy)iodo]benzene
  作者：Om Prakash、Manoj Kumar、Rajesh Kumar

  DOI：10.1016/j.tet.2010.05.042

  日期：2010.7

  substituted monohydric phenols, containing electron-withdrawing substituents at the ortho position to the phenolic group, with [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser’s reagent) leads to novel tosyloxylation of aromatic ring, thereby offering a convenient synthesis of hitherto unknown 4-tosyloxy-2-substituted phenols.

  一些取代的一元酚在酚基邻位含有吸电子取代基，被[羟基（甲苯磺酰氧基）碘]苯（HTIB，Koser试剂）氧化，导致芳香环的新甲苯磺酰化，从而提供了方便的合成方法迄今未知的4-甲苯磺酰氧基-2-取代的酚。
• NOVEL COMPOUNDS
  申请人：Nichols Paula Louise

  公开号：US20120184553A1

  公开（公告）日：2012-07-19

  The present invention relates to novel compounds that inhibit LRRK2 kinase activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases characterised by LRRK2 kinase activity, particularly Parkinson's disease and Alzheimer's disease.

  本发明涉及一种新型化合物，其抑制LRRK2激酶活性，包括其制备过程，含有它们的组合物以及它们在治疗LRRK2激酶活性疾病，特别是帕金森病和阿尔茨海默病中的应用。
• Compounds
  申请人：Nichols Paula Louise

  公开号：US08778939B2

  公开（公告）日：2014-07-15

  The present invention relates to novel compounds that inhibit LRRK2 kinase activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases characterized by LRRK2 kinase activity, particularly Parkinson's disease and Alzheimer's disease.

  本发明涉及一种新型化合物，其抑制LRRK2激酶活性，制备方法，包含它们的组合物以及它们在治疗LRRK2激酶活性疾病，特别是帕金森病和阿尔茨海默病中的应用。