9-(phenylthio)anthracene | 74851-75-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(phenylthio)anthracene
• 英文别名: phenyl 9-anthryl sulfide；9-anthrylphenyl sulfide；9-anthrylphenylsulfide；9-phenylthioanthracene；9-Phenylmercapto-anthracen；9-Phenylthio-anthracen；9-(Phenylsulfanyl)anthracene；9-phenylsulfanylanthracene
• CAS: 74851-75-5
• 化学式: C₂₀H₁₄S
• 分子量: 286.397
• InChiKey: VZNHRVXOOXDJPK-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  487.0±14.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(phenylthio)anthracene 在 溴 、 溶剂黄146 、 苯基锂 作用下， 反应 1.25h， 生成 10-(phenylthio)-9-methylanthracene
  参考文献：
  名称：

  Homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in .alpha.-substituted and 10-substituted 9-methylanthracenes and their related radical anions

  摘要：

  Equilibrium acidities (pK(HA)), reduction potentials E(re)(HA), oxidation potentials E(ox)(HA), and oxidation potentials of the conjugate anions E(ox)(A-) have been measured in dimethylsulfoxide(DMSO) solution for 13 alpha-substituted 9-methylanthracenes (9-GCH2An) and 11 10-substituted 9-methylanthracenes (10-G-9-MeAn). The equilibrium acidities have been shown to be linearly correlated with Hammett sigma- constants. The similar rho- values for the linear correlations of pK(HA) Vs sigma- for 9-GCH2An (rho- = 13.8) and 10-G-9-MeAn (rho- = 14.2) demonstrate that the like substituents in 9-GCH2An and 10-G-9-MeAn have similar large effects on the equilibrium acidities. Suitable combinations of these equilibrium acidities with the reduction and oxidation potentials led to estimates of (a) the homolytic bond dissociation energies (BDE(HA)) of the acidic C-H bonds in 9-GCH2An and 10-G-9-MeAn, (b) the homolytic bond dissociation energies (BDE(HA.-)) of the acidic C-H bonds in 9-GCH2An.- and 10-G-9-MeAn.- radical anions, and (c) the radical cation acidities (pK(HA.+)) of the 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations. Introduction of alpha-CN and alpha-NO2 groups had opposite effects on the strengths (BDE(HA)) of the acidic C-H bonds in 9-GCH2An; the alpha-CN group decreased the BDE(HA) value by 2.5 kcal/mol and the alpha-NO2 increased the BDE(HA) value by 4.5 kcal/mol, but they both weakened the acidic C-H bonds in 9-GCH2An.- radical anions (by 10.6 and 12.5 kcal/mol, respectively). The BDEs of the acidic C-H bonds in 10-G-9-MeAn were estimated to be 81.3 +/- 1.3 kcal/mol and those in the corresponding radical anions were estimated to be 58.5 +/- 2.5 kcal/mol. The 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations are strongly acidic with the pK(HA.+) values estimated in the range of -5 to -11 pK(HA.+) units. Seven linear free energy relationships have been observed.

  DOI：

  10.1021/jo00063a025
• 作为产物：
  描述：

  蒽酮 在 甲烷磺酸 、 硫酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 111.0h， 生成 9-(phenylthio)anthracene
  参考文献：
  名称：

  Useful routes to 9-anthryl ethers and sulfides

  摘要：

  DOI：

  10.1021/jo00164a034

文献信息

• Site-Selective C−S Bond Formation at C−Br over C−OTf and C−Cl Enabled by an Air-Stable, Easily Recoverable, and Recyclable Palladium(I) Catalyst
  作者：Thomas Scattolin、Erdem Senol、Guoyin Yin、Qianqian Guo、Franziska Schoenebeck

  DOI：10.1002/anie.201806036

  日期：2018.9.17

  Computational, spectroscopic, X‐ray, and reactivity data support dinuclear PdI catalysis to be operative. Contrary to air‐sensitive Pd0, the active PdI species was easily recovered in the open atmosphere and subjected to multiple rounds of recycling.

  该报告将新兴的 Pd 催化作用扩展到碳杂原子，即 C−S 键形成。虽然 Pd 0催化方案可能会遇到有毒的硫化物结合的非循环中间体的形成和缺乏选择性的问题，但机械上多样化的 Pd 催化概念规避了这些挑战，并允许 C−S 键形成（S-芳基和 S-烷基） ）多种芳基卤化物。在 C−Cl 和 C−OTf 存在下，C−Br 位点的位点选择性硫醇化是以一般且先验可预测的方式实现的。计算、光谱、X 射线和反应性数据支持双核 Pd 催化是有效的。与空气敏感的 Pd 0相反，活性 Pd 物种很容易在大气中回收并进行多轮回收。
• Microwave-assisted synthesis of substituted phenanthrenes, anthracenes, acenaphthenes, and fluorenes
  作者：Shiuh-Chuan Chan、Jing-Pei Jang、Yie-Jia Cherng

  DOI：10.1016/j.tet.2009.01.029

  日期：2009.3

  Rapid coupling reactions of polycyclic aromatic halides with various N-, S-, and Se-nucleophiles under focused microwave irradiation are described. Using this method, the desired products are obtained with good to excellent yields in a short reaction time.

  描述了在聚焦微波辐射下多环芳族卤化物与各种N-，S-和Se-亲核试剂的快速偶联反应。使用这种方法，可以在短的反应时间内以良好或极好的收率获得所需的产物。
• REACTION OF BENZYNES WITH 9-<i>t</i>-BUTYLTHIOANTHRACENE TO AFFORD 9-<i>t</i>-BUTYLTHIOTRIPTYCENES
  作者：Nobuo Nakamura

  DOI：10.1246/cl.1983.1795

  日期：1983.11.5

  Reaction of benzynes (3a, c, d) with 9-t-butylthioanthracene (2d) resulted in formation of the corresponding 9-t-butylthiotriptycenes (5a, c, d) and 5-t-butylthio-6,ll-dihydro-6,11-ethenonaphthacenes (6a, c, d), while that of 1,4-dimethoxybenzyne (3b) with 2d did not give the corresponding adducts (5b, 6b).

  对苯炔（3a、c、d）与9-叔丁基硫代蒽（2d）的反应生成了相应的9-叔丁基硫代三苯并（5a、c、d）和5-叔丁基硫代-6,11-二氢-6,11-乙烯萘烯（6a、c、d），而1,4-二甲氧基苯炔（3b）与2d的反应则没有生成对应的加成物（5b、6b）。
• Reactions of Haloarenes with Thiolate Anions in Tetraglyme: Competition between electron transfer andSNAr mechanisms
  作者：Stephen D. Pastor

  DOI：10.1002/hlca.19880710421

  日期：1988.6.15

  The reaction of the bromo-substituted naphthalene 1 with the alkanethiolate anions 2a–b and arenethiolate 2c in tetraglyme gave the corresponding 1-naphythyl thio-ethers 3a–c. Thio-ethers 3a–c were oxidized to the corresponding sulfones 4a–c with m- chloroperoxybenzoic acid. The reaction of the dichloro-substituted anthracene 5a with 2b gave the disubstutution product 6a. The reaction of 9-bromoanthracene

  溴代萘1与链烷硫醇根阴离子2a-b和芳硫醇根2c在四甘醇二甲醚中的反应得到相应的1-萘基硫醚3a-c。硫醚3A-C分别氧化成相应的砜4a-c中与米-氯过氧苯甲酸。二氯取代的蒽5a与2b的反应给出了结构产物6a。9-溴蒽的反应5C与烷硫醇2B得到图6b，而反应5C用芳硫醇盐2c得到取代产物6c和蒽7的混合物。观察到6c和7的形成是由取代（S n Ar）和电子转移（ET）机理之间的竞争所解释的。与此解释，一氯-取代的反应一致5b中，它具有一个较高的能量σ *轨道，与图2c，得到6c中，而不形成7.在四甘醇二甲醚的Zn / KOH显示出降低的芳基卤化物5B-C和硫代醚6C到7。
• METHOD OF MANUFACTURING SULTONIUM SALT
  申请人：TOYO GOSEI CO., LTD.

  公开号：US20160068477A1

  公开（公告）日：2016-03-10

  Provided is a sulfonium salt manufacturing method which can reduce the production of a monosulfonium salt. A method of manufacturing a sulfonium salt includes preparing a first sulfonium salt containing a sulfonium cation and a first anion, preparing a second sulfonium salt by exchanging the first anion for a halide ion, and preparing a third sulfonium salt by exchanging the halide ion for a second anion.

  提供一种亚砜盐的制备方法，可以减少单亚砜盐的产生。制备亚砜盐的方法包括：准备含有亚砜阳离子和第一阴离子的第一亚砜盐，通过将第一阴离子与卤离子交换来制备第二亚砜盐，通过将卤离子与第二阴离子交换来制备第三亚砜盐。