9-(4-tolyl)thioxanthen-9-ol | 113493-35-9

• 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-tolyl)thioxanthen-9-ol
• 英文别名: 9-(4-methylphenyl)thioxanthenol；9-(4-methylphenyl)-9H-thioxanthen-9-ol；9-(4-methylphenyl)thioxanthen-9-ol
• CAS: 113493-35-9
• 化学式: C₂₀H₁₆OS
• 分子量: 304.412
• InChiKey: ULRWNNKPVSLURB-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166 °C
• 沸点：
  472.8±24.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  9-(4-tolyl)thioxanthen-9-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到9-(p-methylphenyl)-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-噻吨酮 、 对甲苯基溴化镁 生成 9-(4-tolyl)thioxanthen-9-ol
  参考文献：
  名称：

  Tricylic amino-acid derivatives

  摘要：

  本文描述了具有以下一般式的化合物：##STR1##或其前药或药用可接受的盐、溶剂或水合物，其中：R.sup.1选自H、烷基和碱性加成盐的对离子组成的群；X选自CR.sup.9 R.sup.10、S、O、SO、SO.sub.2、NH和N-烷基的群；R.sup.2、R.sup.3、R.sup.4、R.sup.9和R.sup.10独立地选自H和烷基的群；R.sup.5和R.sup.6独立地选自H、烷基和苯基，或者，作为另一选择，R.sup.5和R.sup.6可以一起形成亚甲基基团或3-至6-成员的螺环基团；当X为CR.sup.9 R.sup.10时，R.sup.5和R.sup.9或R.sup.6和R.sup.10中的一个或两个对可能连接以形成双键或三键R.sup.7选自以下式II-V的群：##STR2##它们都可以在除R.sup.8之外的节点上选择性地取代，取代基独立地选自烷基、卤素、芳基（可能像R.sup.8那样被取代）、三氟甲基、三氟甲氧基、硝基、氰基、氨基、单烷基氨基、双烷基氨基、烷氧羰基、烷基羰基、烷氧硫代羰基、烷基硫代羰基、烷氧基、烷基硫、苯氧基、--SO.sub.2 NH.sub.2、--SO.sub.2 NH烷基、--SO.sub.2 N(烷基).sub.2和1,2-亚甲二氧基；结构II至V中的苯并环中的任何一个都可以被选择自吡啶、噻吩、呋喃和吡咯的5-或6-成员杂环环取代；其中R.sup.8选自H、烷基、苄基、环烷基、茚基和一个可选择性取代的芳基，其中可选择性取代基独立地选自烷基、卤素、芳基、三氟甲基、三氟甲氧基、硝基、氰基、氨基、单烷基氨基、双烷基氨基、烷氧羰基、烷基羰基、烷氧硫代羰基、烷基硫代羰基、烷氧基、烷基硫、苯氧基、--SO.sub.2 NH.sub.2、--SO.sub.2 NH烷基、--SO.sub.2 N(烷基).sub.2和1,2-亚甲二氧基；--表示单键或双键；Y选自O、S、SO、NH、N-烷基、CH.sub.2、CH-烷基、C(烷基).sub.2和C.dbd.O的群；当--为单键时，Z选自CH.sub.2、O、S、NH和N-烷基的群；当--为双键时，Z选自CH和N的群。还描述了这些化合物作为药物的用途。

  公开号：

  US06162824A1

文献信息

• 9-Phenylxanthen-9-ylium and 9-Phenylthioxanthen-9-ylium Ions: Comparison of<i>o</i>- and<i>p</i>-Substitutions in the 9-Phenyl Group by Cyclic Voltammetry and Visible Spectra
  作者：Tatsuo Erabi、Masahiro Asahara、Masahumi Miyamoto、Keisuke Goto、Masanori Wada

  DOI：10.1246/bcsj.75.1325

  日期：2002.6

  9-Arylxanthen-9-ylium (3a–i) and 9-arylthioxanthen-9-ylium (4a,b,e–i) perchlorates [aryl = 2,4,6-(MeO)3C6H2 (a), 2,6-(MeO)2C6H3 (b), 2-MeOC6H4 (c), 4-MeOC6H4 (d), 3-Br-2,6-(MeO)2C6H2 (e), 2,4,6-Me3C6H2 (f), 2-MeC6H4 (g), 4-MeC6H4 (h), C6H5 (i)] were prepared by the reactions of 9-arylxanthen-9-ols or 9-arylthioxanthen-9-ols with perchloric acid. Their LUMO and HOMO levels were estimated from the redox potential (E0) in cyclic voltammetry and λmax in the UV–visible spectra measured for a 1,2-dichloroethane solution, and were compared with those of 9-aryl-1,8-dimethoxyxanthen-9-ylium ions (8b,i). We found that 1) both the LUMO and HOMO levels varied almost in the same order of substituent on the 9-phenyl group; 2) the MeO-group on the 9-phenyl group was more effective to raise both the HOMO and LUMO levels than the Me-group; 3) the HOMO levels of 3 and 4 were more sensitive than the LUMO levels to the change in the 9-aryl group; 4) p-substitution by MeO- or Me-groups was more effective to raise the HOMO and LUMO levels than o-substitution; 5) the presence of two o-MeO groups was more effective to raise the HOMO and LUMO levels than one o-MeO group; 6) a m-bromination of 9-aryl group in 3b or 4b greatly lowered both LUMO and HOMO levels, as observed for 3e or 4e; 7) both the HOMO and LUMO levels of 8b and 8i were higher than those of 3b and 3i, respectively; 8) the LUMO level of 3b was higher than that of 8i, the isomer.

  9- 芳基氧杂蒽-9-基 (3a-i) 和 9- 芳基硫杂蒽-9-基 (4a,b,e-i) 高氯酸盐 [芳基 = 2,4,6-(MeO)3C6H2 (a)、2,6-(MeO)2C6H3 (b)、2-MeOC6H4 (c)、4-MeOC6H4 (d)、3-Br-2、6-(MeO)2C6H2 (e)、2,4,6-Me3C6H2 (f)、2-MeC6H4 (g)、4-MeC6H4 (h)、C6H5 (i)]是由 9-芳基氧杂蒽-9-醇或 9-芳基硫杂蒽-9-醇与高氯酸反应制备的。根据循环伏安法测得的氧化还原电位（E0）和在 1,2 二氯乙烷溶液中测得的紫外可见光谱中的λmax 值估算了它们的 LUMO 和 HOMO 水平，并将其与 9-芳基-1,8-二甲氧基氧杂蒽-9-鎓离子（8b,i）的 LUMO 和 HOMO 水平进行了比较。我们发现：1）9-苯基上的 LUMO 和 HOMO 水平几乎按照相同的取代基顺序变化；2）9-苯基上的 MeO 基团比 Me 基团更能提高 HOMO 和 LUMO 水平；3) 与 LUMO 水平相比，3 和 4 的 HOMO 水平对 9-芳基的变化更为敏感；4) 与 o 取代相比，MeO 或 Me 取代更有效地提高了 HOMO 和 LUMO 水平；5) 两个 o-MeO 基团的存在比一个 o-MeO 基团更有效地提高了 HOMO 和 LUMO 水平；6) 与 3e 或 4e 一样，3b 或 4b 中 9- 芳基的 m-bromination 大大降低了 LUMO 和 HOMO 水平；7) 8b 和 8i 的 HOMO 和 LUMO 水平分别高于 3b 和 3i；8) 3b 的 LUMO 水平高于同分异构体 8i。
• 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.
• MARYANOFF B. E.; STACKHOUSE J.; SENKLER JR. G. H.; MISLOW K., J. AMER. CHEM. SOC. <JACS-AT>, 1975, 97, NO 10, 2718-2742
  作者：MARYANOFF B. E.、 STACKHOUSE J.、 SENKLER JR. G. H.、 MISLOW K.

  DOI：——

  日期：——
• 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：——