9-(4-methoxyphenyl)thioxanthenol | 52844-97-0

• 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-methoxyphenyl)thioxanthenol
• 英文别名: 9-(4-methoxy-phenyl)-thioxanthen-9-ol；9-(4-Methoxyphenyl)thioxanthen-9-ol
• CAS: 52844-97-0
• 化学式: C₂₀H₁₆O₂S
• 分子量: 320.412
• InChiKey: TYFBPQOPVFUITN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(4-methoxyphenyl)thioxanthenol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到9-(p-methoxyphenyl)-10-oxothioxanthen-9-ol
  参考文献：
  名称：

  S(O)-Pixyl protecting group as efficient mass-tag

  摘要：

  我们在此报告了一种新型三苯基甲基标签的设计、制备及其首次应用，该标签具有可调节的稳定性，作为保护基或质谱分析物有效。

  DOI：

  10.1039/b504913j
• 作为产物：
  描述：

  9-(4-methoxyphenyl)-9H-thioxanthen-9-ylium 在 水 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 9-(4-methoxyphenyl)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.
• Rate Constants and Activation Energies for the Reactions of Triphenylmethyl and 9-Arylthioxanthyl Radicals with Dioxygen.
  作者：Haijiang Wang、Vernon D. Parker、Gang Zheng、Haijiang Wang、Jose Maria Moreno、Antonio Romerosa、Ward T. Robinson、Björn O. Roos、Claire Vallance、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0865

  日期：——

  Triphenylmethyl radical reacts with dioxygen in dichloromethane with a second-order rate constant of 1.1 x 10(7) dm(3) mol(-1) s(-1) at 298 K and an Arrhenius activation energy of -4.1 kcal mol(-1). 4-Phenyl-substituted thioxanthyl radicals are somewhat less reactive toward dioxygen in acetonitrile (second-order rate constants from 1.4 x 10(5) to 3.2 x 10(5) dm3 mol(-1) s(-1) at 298 K with Arrhenius activation energies of about -3 kcal mol(-1)). A weak substituent effect (p=-0.45) was observed for the latter reaction series. The major products of these reactions are the corresponding carbonyl compounds, benzophenone and thioxanthone, believed to form by rearrangement after rate determining adduct formation between the radicals and dioxygen. The mechanism of adduct formation is believed to occur in two steps involving the formation of a complex in a pre-equilibrium followed by bond formation.
• NAGAO;YUKINORI;ABE, YUKIHIRO;OYAMA, TSUKASA;ABE, YOSHIMOTO;MISONO, TAKAHI+, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1987) N 10, 1839-1845
  作者：NAGAO、YUKINORI、ABE, YUKIHIRO、OYAMA, TSUKASA、ABE, YOSHIMOTO、MISONO, TAKAHI+

  DOI：——

  日期：——
• S(O)-Pixyl protecting group as efficient mass-tag
  作者：Pablo L. Bernad, Jr、Safraz Khan、Vladimir A. Korshun、Edwin M. Southern、Mikhail S. Shchepinov

  DOI：10.1039/b504913j

  日期：——

  We report herein the design, preparation and first applications of novel trityl tags with adjustable stability, efficient as protecting groups or MS analytes.

  我们在此报告了一种新型三苯基甲基标签的设计、制备及其首次应用，该标签具有可调节的稳定性，作为保护基或质谱分析物有效。
• 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。