2-chloro-9-phenylthioxanthenol | 476331-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: 2-chloro-9-phenylthioxanthenol
• 英文别名: 2-Chloro-10-phenyl-10H-dibenzo[B,E]thiopyran-10-OL；2-chloro-9-phenylthioxanthen-9-ol
• CAS: 476331-76-7
• 化学式: C₁₉H₁₃ClOS
• 分子量: 324.831
• InChiKey: IUNGAZPEFGEIRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-9-phenylthioxanthenol 在 三甲基氯硅烷 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 2,9-Dichloro-9-phenyl-9H-thioxanthene
  参考文献：
  名称：

  S-Pixyl Analogues as Photocleavable Protecting Groups for Nucleosides

  摘要：

  Several analogues of the 9-phenylthioxanthyl (S-pixyl) photocleavable protecting group have been synthesized, containing substituents on the 9-aryl ring and on the thioxanthyl backbone. Each analogue protected the 5'-hydroxy moiety of thymidine in good to excellent yield. The protected substrates were deprotected in 1:1 water: acetonitrile with irradiation at 300 nm, resulting in recovered thymidine in excellent yield, except for the nitro-substituted analogues which gave substantially lower yields. Substrates with 2,7-dibromo or 3-methoxy substitution on the thioxanthyl backbone were also deprotected efficiently with irradiation at 350 nm. Shorter irradiation times were observed in the less nucleophilic solvent mixture of 1:9 trifluoroethanol:acetonitrile, with no formation of secondary photooxidation products. Photodeprotection with high yields was also achieved in the absence of solvent, with no secondary photoproducts.

  DOI：

  10.1021/jo026009w
• 作为产物：
  描述：

  溴苯 、 2-氯噻吨酮 在 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以83%的产率得到2-chloro-9-phenylthioxanthenol
  参考文献：
  名称：

  S-Pixyl Analogues as Photocleavable Protecting Groups for Nucleosides

  摘要：

  Several analogues of the 9-phenylthioxanthyl (S-pixyl) photocleavable protecting group have been synthesized, containing substituents on the 9-aryl ring and on the thioxanthyl backbone. Each analogue protected the 5'-hydroxy moiety of thymidine in good to excellent yield. The protected substrates were deprotected in 1:1 water: acetonitrile with irradiation at 300 nm, resulting in recovered thymidine in excellent yield, except for the nitro-substituted analogues which gave substantially lower yields. Substrates with 2,7-dibromo or 3-methoxy substitution on the thioxanthyl backbone were also deprotected efficiently with irradiation at 350 nm. Shorter irradiation times were observed in the less nucleophilic solvent mixture of 1:9 trifluoroethanol:acetonitrile, with no formation of secondary photooxidation products. Photodeprotection with high yields was also achieved in the absence of solvent, with no secondary photoproducts.

  DOI：

  10.1021/jo026009w

文献信息

• HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
  申请人：Samsung Display Co., Ltd.

  公开号：US20180237460A1

  公开（公告）日：2018-08-23

  An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer comprising an emission layer comprising the heterocyclic compound of Formula 1 as a host or as a delayed fluorescent dopant. The organic light-emitting device including the heterocyclic compound may have a low driving voltage and excellent maximum quantum efficiency:

  一种有机发光器件包括：第一电极，第二电极与第一电极相对，以及第一电极和第二电极之间的有机层，该有机层包括一个发射层，该发射层包括式1的杂环化合物作为主体或延迟荧光掺杂剂。包括该杂环化合物的有机发光器件可以具有低驱动电压和优异的最大量子效率。
• Heterocyclic compound and organic light-emitting device including the same
  申请人：Samsung Display Co., Ltd.

  公开号：US10954254B2

  公开（公告）日：2021-03-23

  An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer comprising an emission layer comprising the heterocyclic compound of Formula 1 as a host or as a delayed fluorescent dopant. The organic light-emitting device including the heterocyclic compound may have a low driving voltage and excellent maximum quantum efficiency:

  一种有机发光器件包括：第一电极；面向第一电极的第二电极；以及位于第一电极和第二电极之间的有机层，该有机层包括发射层，该发射层包含作为宿主或作为延迟荧光掺杂剂的式 1 杂环化合物。包括杂环化合物的有机发光器件可具有较低的驱动电压和出色的最大量子效率：
• S-Pixyl Analogues as Photocleavable Protecting Groups for Nucleosides
  作者：Michael P. Coleman、Mary K. Boyd

  DOI：10.1021/jo026009w

  日期：2002.11.1

  Several analogues of the 9-phenylthioxanthyl (S-pixyl) photocleavable protecting group have been synthesized, containing substituents on the 9-aryl ring and on the thioxanthyl backbone. Each analogue protected the 5'-hydroxy moiety of thymidine in good to excellent yield. The protected substrates were deprotected in 1:1 water: acetonitrile with irradiation at 300 nm, resulting in recovered thymidine in excellent yield, except for the nitro-substituted analogues which gave substantially lower yields. Substrates with 2,7-dibromo or 3-methoxy substitution on the thioxanthyl backbone were also deprotected efficiently with irradiation at 350 nm. Shorter irradiation times were observed in the less nucleophilic solvent mixture of 1:9 trifluoroethanol:acetonitrile, with no formation of secondary photooxidation products. Photodeprotection with high yields was also achieved in the absence of solvent, with no secondary photoproducts.