(3,5-dimethylphenyl)(trifluoromethyl)sulfane | 129724-23-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3,5-dimethylphenyl)(trifluoromethyl)sulfane
• 英文别名: 1,3-Dimethyl-5-(trifluoromethylsulfanyl)benzene；1,3-dimethyl-5-(trifluoromethylsulfanyl)benzene
• CAS: 129724-23-8
• 化学式: C₉H₉F₃S
• 分子量: 206.232
• InChiKey: ORTWZUTWUKGBNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二甲基苯硫酚 在 吡啶 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 4.58h， 生成 (3,5-dimethylphenyl)(trifluoromethyl)sulfane
  参考文献：
  名称：

  10.1002/ejoc.202400542

  摘要：

  A practical and efficient trifluoromethylation of readily available and bench stable N‐Thiophthalimides and N‐Thioimides with Ruppert‐Prakash reagent (TMS‐CF3) is described. The reaction proceeds at room temperature and only requires NaOAc as the mild promoter to prepare a series of trifluoromethyl thioethers in good to excellent yields. Both aryl and alkyl derivates are well trifluoromethylated under transition‐metal‐free reaction conditions. Moreover, the reaction features with scale‐up synthesis and late‐stage modification of bioactive molecule.

  DOI：

  10.1002/ejoc.202400542

文献信息

• Copper-catalyzed synthesis of aryl and alkyl trifluoromethyl sulfides using CF3SiMe3 and Na2S2O3 as –SCF3 source
  作者：Wei Zhong、Xiaoming Liu

  DOI：10.1016/j.tetlet.2014.07.039

  日期：2014.8

  universal and efficient Cu(I)-catalyzed synthesis of aryl and alkyl trifluoromethyl sulfides has been developed. In this catalytic system, S-aryl or S-alkyl sulfothioate (I or II) proved to be the key intermediate. Substrates bearing groups of I, Br, Cl, OTs, and OMs on the aryl carbon and no matter electron-withdrawing and electron-donating substitutions on the aromatic ring could afford good to excellent

  已经开发出通用且有效的Cu（I）催化的芳基和烷基三氟甲基硫醚的合成方法。在该催化体系中，S-芳基或S-烷基磺基硫酸酯（Ⅰ或Ⅱ）被证明是关键的中间体。在芳基碳上带有I，Br，Cl，OTs和OMs的基团的基团，无论芳环上有吸电子和供电子取代基，都可以提供优异的良率。
• Copper-Catalyzed Trifluoromethylthiolation of Di(hetero)aryl-λ³-iodanes: Mechanistic Insight and Application to Synthesis of (Hetero)Aryl Trifluoromethyl Sulfides
  作者：Perumal Saravanan、Pazhamalai Anbarasan

  DOI：10.1002/adsc.201500606

  日期：2015.11.16

  The direct and regioselective copper/S-Phos-catalyzed trifluoromethylthiolation of symmetrical and unsymmetrical di(hetero)aryl-λ3-iodanes has been accomplished for the synthesis of various (hetero)aryl trifluoromethyl sulfides employing readily accessible silver trifluoromethylthiolate (AgSCF3) as nucleophilic trifluoromethylthiolating reagent. The developed transformation tolerates various functional

  直接和区域选择性铜/ S-PHOS催化对称和不对称二（杂）芳基- λ的trifluoromethylthiolation 3 -iodanes已经关于各种（杂）的合成芳基三氟甲基硫醚采用容易获得银trifluoromethylthiolate完成（AgSCF 3）作为亲核三氟甲基硫醇化试剂。发达的转化反应可耐受各种官能团，例如腈，烯醇化的酮，酯，硝基和游离羧酸。有趣的是，芳烃的正式trifluoromethylthiolation通过二芳基λ的合成的融合也达到3芳烃中的三氟甲基硫醇。机理研究不利于自由基形成和SET途径。基于可变温度19 F NMR光谱中，最相关的催化中间体，和化学计量研究隔离支撑在Cu（I）/铜（III）催化循环，其中，所述氧化加成二芳基- λ的3个-iodanes由辅助银盐。
• Copper-mediated oxidative trifluoromethylthiolation of aryl boronic acids with CF3CO2Na and elemental sulfur
  作者：Lijuan Zhai、Yaming Li、Jun Yin、Kun Jin、Rong Zhang、Xinmei Fu、Chunying Duan

  DOI：10.1016/j.tet.2013.10.028

  日期：2013.12

  A practical three-component copper-mediated oxidative trifluoromethylthiolation of aryl boronic acids with cheap and readily available sodium trifluoroacetate and elemental sulfur is reported. A variety of trifluoromethylthio-substituted aromatics are synthesized in moderate yields under mild reaction conditions.

  据报道，用便宜且容易获得的三氟乙酸钠和元素硫对芳基硼酸进行三组分铜介导的氧化三氟甲基硫醇化反应。在温和的反应条件下，以中等收率合成了多种三氟甲硫基取代的芳族化合物。
• Nickel-Catalyzed Synthesis of Aryl Trifluoromethyl Sulfides at Room Temperature
  作者：Cheng-Pan Zhang、David A. Vicic

  DOI：10.1021/ja210364r

  日期：2012.1.11

  Inexpensive nickel-bipyridine complexes were found to be active for the trifluoromethylthiolation of aryl iodides and aryl bromides at room temperature using the convenient [NMe4][SCF3] reagent.