4-tosyloxy-2H-1-benzothiopyran-2-one | 870641-13-7

• 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: 4-tosyloxy-2H-1-benzothiopyran-2-one
• 英文别名: 2-oxo-2H-thiochromen-4-yl 4-methylbenzenesulfonate；2-oxo-2H-thiochromen-4-yl tosylate；(2-Oxothiochromen-4-yl) 4-methylbenzenesulfonate
• CAS: 870641-13-7
• 化学式: C₁₆H₁₂O₄S₂
• 分子量: 332.401
• InChiKey: NWZDRSHQMIYGDA-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  488.3±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-tosyloxy-2H-1-benzothiopyran-2-one 在 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  氧化胺重排的研究：吡咯并[3,2-c][1]苯并噻喃-4-酮的合成

  摘要：

  摘要 一种基于串联 [2,3] 和 [3,3] sigmatropic 重排的方法已被描述用于合成迄今为止未报道的、具有潜在生物活性的吡咯并[3,2-c][1]苯并噻喃-4-酮。 6a-g) 衍生物。

  DOI：

  10.1080/00397910500518908
• 作为产物：
  描述：

  1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 、 2-hydroxythiochromen-4-one 在 三乙烯二胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以83%的产率得到4-tosyloxy-2H-1-benzothiopyran-2-one
  参考文献：
  名称：

  1-磺酰基-1H-1,2,3-三唑的无过渡金属和无氧化剂磺酰化为烯醇，用于合成磺酸盐衍生物

  摘要：

  摘要 建立了一种通过 DABCO 催化的 1-磺酰基-1,2,3-三唑直接磺酰化为不同烯醇合成磺酸盐衍生物的新型便捷方案。该合成路线可以有效地避免使用过渡金属催化剂和额外的氧化剂，在温和条件下，低催化剂负载量下可以以良好到优异的收率（75-86％）获得目标产物，具有广泛的底物范围，这将提供轻松实用地获得烯醇磺酸盐。此外，通过 Suzuki-Miyaura、Sonogashira 和 Heck 交叉偶联反应证明了使用所得烯醇磺酸盐形成 CC 键。图形概要

  DOI：

  10.1080/00397911.2019.1582065

文献信息

• Facile synthesis of 4-acetyl-coumarins, -thiocoumarin and -quinolin-2(1H)-one via very high α-regioselective Heck coupling on tosylates
  作者：Sergio Valente、Gilbert Kirsch

  DOI：10.1016/j.tetlet.2011.04.033

  日期：2011.7

  An efficient synthesis of a series of methyl ketones at the C4 position of coumarins, coumarin-containing heterocycles and analogous scaffolds is reported via very high α-regioselective Heck coupling using tosylates and in very high yields. Although α-regioselectivity in Heck coupling can be obtained with triflates as substrates, tosylates are less toxic, less expensive and, importantly, more stable

  据报道，通过使用甲苯磺酸盐的非常高的α-区域选择性Heck偶联，并以非常高的收率，在香豆素，含香豆素的杂环和类似支架的C4位有效合成了一系列甲基酮。尽管可以用三氟甲磺酸酯作为底物获得Heck偶联中的α-区域选择性，但是甲苯磺酸盐的毒性较小，价格较低并且重要的是更稳定。
• Photocycloaddition of 4-(Alk-1-ynyl)-Substituted Coumarins and Thiocoumarins to 2,3-Dimethylbuta-1,3-diene
  作者：Inga Inhülsen、Karin Chin、Maren Göwert、Paul Margaretha

  DOI：10.1002/hlca.201100112

  日期：2011.6

  AbstractOn irradiation (350 nm) in the presence of 2,3‐dimethylbuta‐1,3‐diene (8), 4‐(alk‐1‐ynyl)coumarins 1 afford mixtures of cyclobuta‐ and cycloocta‐annulated products 9 and 10, respectively. In contrast, the corresponding thiocoumarins 2 react with the same diene chemoselectively to give cyclohexa‐annulated products 11.
• Light-Induced Coumarin Cyclopentannelation
  作者：Marko Soltau、Maren Göwert、Paul Margaretha

  DOI：10.1021/ol051952i

  日期：2005.11.1

  Whereas cyclopentenylcarbenes resulting from photocycloaddition of 4-alk-1-ynylcoumarins to 2,3-dimethylbut-2-ene undergo tandem cyclization to hitherto unknown tetracyclic (4-hetera)cyclopent[b, c]acenaphthylenes, the corresponding cyclopentenylnitrenes stemming from 4-cyanocoumarins and the same alkene are converted into tricyclic imines via H-abstraction.
• Near Infrared Ray Activation Type Positive Resin Composition
  申请人：Imai Genji

  公开号：US20070259279A1

  公开（公告）日：2007-11-08

  A near infrared ray activation type positive resist composition comprising (A) a vinyl-based polymer having a monomer unit having an alkali-soluble group blocked by an ether having an alkenyl group next to an ether oxygen, (B) a photothermal converting substance generating heat by a light in the near infrared region, (C) a thermal acid generator generating an acid by heat, can provide a near infrared ray activation type positive resist composition which can be subjected to an exposure treatment in a complete bright room such as under a white light and the like, gives desired sensitivity and resolution, and of which baking treatment conditions can be relaxed or a baking treatment can be omitted, and a pattern formation method using the same.
• Positive resist composition for recording medium master, and method of producing recording medium master and method of producing stamper using the same
  申请人：Imai Genji

  公开号：US20090045552A1

  公开（公告）日：2009-02-19

  Provided are a positive resist composition for recording medium master showing excellent plating resistance and adhesion to a base plate such as glass or the like characterized by containing a vinyl polymer which has a monomer unit having an alkali-soluble group blocked by an alkyl vinyl ether, and a method of producing a recording medium master or stamper using this positive resist composition.