9-(4-fluorophenyl)thioxanthenol | 82761-37-3

• 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: 9-(4-fluorophenyl)thioxanthenol
• 英文别名: 9-(4-fluorophenyl)-9H-thioxanthen-9-ol；9-(4-Fluorophenyl)thioxanthen-9-ol；9-(4-fluorophenyl)thioxanthen-9-ol
• CAS: 82761-37-3
• 化学式: C₁₉H₁₃FOS
• 分子量: 308.376
• InChiKey: HSZRXHVGVMJAPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  3

反应信息

• 作为反应物：
  描述：

  9-(4-fluorophenyl)thioxanthenol 在 4-二甲氨基吡啶 、 三甲基氯硅烷 作用下， 以 吡啶 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 5'-O-[9-(4-fluorophenyl)thioxanthyl]thymidine
  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：

  9-(p-fluorophenyl)thioxanthenium cation 在 水 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 9-(4-fluorophenyl)thioxanthenol
  参考文献：
  名称：

  噻吨阳离子：具有可调颜色和湿度敏感性的高度可逆水致变色材料

  摘要：

  thioxanthylium 阳离子/thioxanthene-9-ol 的氢致变色可以通过结构功能化进行调整，以提供不同的颜色和湿度敏感性。这种可逆的水致变色系统很容易被化学稳定前体中的有机酸激活，从而可能用于湿度感应和防伪加密。

  DOI：

  10.1002/chem.202201975

文献信息

• 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.
• Thioxanthylium Cations: Highly Reversible Hydrochromic Mate‐rials with Tunable Color and Moisture Sensitivity
  作者：Ming Hui Chua、Xiang Yun Debbie Soo、Wei Peng Goh、Zhuang Mao Png、Qiang Zhu、Jianwei Xu

  DOI：10.1002/chem.202201975

  日期：2022.11.21

  Hydrochromism of thioxanthylium cations/ thioxanthene-9-ol can be tuned by structural functionalization to offer diverse colors and moisture-sensitivities. This reversible hydrochromic system is easily activated with organic acid from chemically stable precursors, allowing for possible uses in moisture-sensing and anti-counterfeiting encryption.

  thioxanthylium 阳离子/thioxanthene-9-ol 的氢致变色可以通过结构功能化进行调整，以提供不同的颜色和湿度敏感性。这种可逆的水致变色系统很容易被化学稳定前体中的有机酸激活，从而可能用于湿度感应和防伪加密。