tert-butyl 5-((trifluoromethyl)thio)-1H-indole-1-carboxylate | 1333415-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl 5-((trifluoromethyl)thio)-1H-indole-1-carboxylate
• 英文别名: Tert-butyl 5-(trifluoromethylsulfanyl)indole-1-carboxylate
• CAS: 1333415-93-2
• 化学式: C₁₄H₁₄F₃NO₂S
• 分子量: 317.332
• InChiKey: SMIFNPAKFRLWSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-((trifluoromethyl)thio)-1H-indole-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-((trifluoromethyl)thio)-1H-indole
  参考文献：
  名称：

  TRYPTAMINE COMPOUNDS, COMPOSITIONS, AND METHODS OF USE

  摘要：

  The present disclosure relates to tryptamine compounds, and pharmaceutically acceptable salts, stereoisomers, tautomers, solvates, polymorphs, or prodrugs thereof, to pharmaceutical compositions, and in some embodiments, to serotonin 5-HT2receptor agonists and uses in the treatment of diseases such as those diseases associated with a 5-HT2receptor.

  公开号：

  WO2024046837A1
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 5-碘吲哚 在 4-二甲氨基吡啶 、 苯基三乙基碘化铵 、 [(cod)Pd(CH₂TMS)₂] 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 tert-butyl 5-((trifluoromethyl)thio)-1H-indole-1-carboxylate
  参考文献：
  名称：

  TRYPTAMINE COMPOUNDS, COMPOSITIONS, AND METHODS OF USE

  摘要：

  The present disclosure relates to tryptamine compounds, and pharmaceutically acceptable salts, stereoisomers, tautomers, solvates, polymorphs, or prodrugs thereof, to pharmaceutical compositions, and in some embodiments, to serotonin 5-HT2receptor agonists and uses in the treatment of diseases such as those diseases associated with a 5-HT2receptor.

  公开号：

  WO2024046837A1

文献信息

• Pd-Catalyzed Synthesis of ArSCF3 Compounds under Mild Conditions
  作者：Georgiy Teverovskiy、David S. Surry、Stephen L. Buchwald

  DOI：10.1002/anie.201102543

  日期：2011.8.1

  Good to excellent yields of aryl trifluoromethyl sulfides, which are an important class of compounds in both the pharmaceutical and agrochemical areas, can be achieved under mild conditions by the Pd‐catalyzed reaction of aryl bromides with a trifluoromethylthiolate nucleophile (see scheme).

  通过芳基溴化物与三氟甲基硫醇盐亲核试剂的 Pd 催化反应，芳基三氟甲基硫化物是制药和农用化学品领域的一类重要化合物，可在温和条件下获得良好至极好的收率（参见方案）。
• Fundamental Studies and Development of Nickel-Catalyzed Trifluoromethylthiolation of Aryl Chlorides: Active Catalytic Species and Key Roles of Ligand and Traceless MeCN Additive Revealed
  作者：Guoyin Yin、Indrek Kalvet、Ulli Englert、Franziska Schoenebeck

  DOI：10.1021/jacs.5b00538

  日期：2015.4.1

  A catalytic protocol to convert aryl and heteroaryl chlorides to the corresponding trifluoromethyl sulfides is reported herein. It relies on a relatively inexpensive Ni(cod)(2)/dppf (cod = 1,5-cyclooctadiene; dppf = 1,1'-bis(diphenylphosphino)ferrocene) catalyst system and the readily accessible coupling reagent (Me4N)SCF3. Our computational and experimental mechanistic data are consistent with a Ni-(0)/Ni-(II) cycle and inconsistent with Ni-(I) as the reactive species. The relevant intermediates were prepared, characterized by X-ray crystallography, and tested for their catalytic competence. This revealed that a monomeric tricoordinate Ni-(I) complex is favored for dppf and Cl whose role was unambiguously assigned as being an off-cycle catalyst deactivation product. Only bidentate ligands with wide bite angles (e.g., dppf) are effective. These bulky ligands render the catalyst resting state as [(P-P)Ni(cod)]. The latter is more reactive than Ni(P-P)(2), which was found to be the resting state for ligands with smaller bite angles and suffers from an initial high-energy dissociation of one ligand prior to oxidative addition, rendering the system unreactive. The key to effective catalysis is hence the presence of a labile auxiliary ligand in the catalyst resting state. For more challenging substrates, high conversions were achieved via the employment of MeCN as a traceless additive. Mechanistic data suggest that its beneficial role lies in decreasing the energetic span, therefore accelerating product formation. Finally, the methodology has been applied to synthetic targets of pharmaceutical relevance.