1-((trifluoromethyl)thio)isoquinoline | 1352009-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-((trifluoromethyl)thio)isoquinoline
• 英文别名: 1-((Trifluoromethyl)thio)isoquinoline；1-(trifluoromethylsulfanyl)isoquinoline
• CAS: 1352009-96-1
• 化学式: C₁₀H₆F₃NS
• 分子量: 229.226
• InChiKey: ABMDFELEDNDIBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-氯异喹啉 在 叔丁基过氧化氢 、 copper(l) iodide 、 硫脲 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 1-((trifluoromethyl)thio)isoquinoline
  参考文献：
  名称：

  Chemoselective Perfluoromethylation of Thio- and Selenoamides

  摘要：

  A chemo- and regioselective perfluoromethylation using thioamides/selenoamides (prepared one step from corresponding lactams) as starting materials has been discovered. The reaction demonstrated complementary chemoselectivity to the C-H trifluoromethylation of (hetero)arenes as well as remarkable functional group compatibility especially toward radical sensitive olefin-, alkyne-, and arylhalide-bearing substrates. The examples of perfluorothio-/selenolated drug molecules indicated application potential of this strategy in drug modification and drug-analogue preparation.

  DOI：

  10.1021/acs.orglett.0c03241

文献信息

• Regioselective deoxygenative C H trifluoromethylthiolation of heteroaryl N-oxides with AgSCF3
  作者：Shi-Bo Zhang、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1016/j.jfluchem.2019.109367

  日期：2019.11

  trifluoromethylthiolation of heteroaryl N-oxides with AgSCF3 is presented, employing p-toluenesulfonic anhydride and tetra-n-butylammonium iodide as the activators. This reaction delivers a series of C2-trifluoromethylthiolated heteroaromatic compounds in moderate to excellent yields. It provides a complementary method for CH trifluoromethylthiolation reactions.

  提出了一种温和有效的方法，采用对甲苯磺酸酐和碘化四正丁基铵作为活化剂，用AgSCF 3进行杂芳基N-氧化物的区域选择性脱氧CH 3三氟甲基硫醇化。该反应以中等至优异的产率产生了一系列的C2-三氟甲基硫醇化的杂芳族化合物。它为C H三氟甲基硫醇化反应提供了一种补充方法。
• Trifluoromethylthiolation of Aryl Iodides and Bromides Enabled by a Bench-Stable and Easy-To-Recover Dinuclear Palladium(I) Catalyst
  作者：Guoyin Yin、Indrek Kalvet、Franziska Schoenebeck

  DOI：10.1002/anie.201501617

  日期：2015.6.1

  Described herein is the concept of alternative cross‐coupling cycles with a more robust (air‐, moisture‐, and thermally‐stable) dinuclear PdI complex, thus avoiding the handling of sensitive Pd0 species or ligands. Highly efficient CSCF3 coupling of a range of aryl iodides and bromides was achieved, and the recovery of the PdI complex was accomplished via simple open‐atmosphere column chromatography.

  尽管钯催化在现代化学研究中无处不在，但是在常规实验室应用下如何回收活性过渡金属络合物常常是一项挑战。本文描述的是具有更健壮（空气，湿气和热稳定）双核Pd I配合物的交替交叉偶联循环的概念，从而避免了对敏感的Pd 0物种或配体的处理。高度高效的C  SCF 3的范围内的芳基碘化物和溴化物的耦合达到了，并且PD的恢复余复合物通过简单的开气氛柱色谱法来完成。动力学和计算数据支持双核Pd I催化的可行性。新颖的SCF分离了3桥的Pd I二聚体，通过X射线晶体学表征，并证明是有效的催化中间体。
• 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.
• CN116102507
  申请人：——

  公开号：——

  公开（公告）日：——
• Chemoselective Perfluoromethylation of Thio- and Selenoamides
  作者：Xianhong Xu、Jianyu Zhang、Tao Xu

  DOI：10.1021/acs.orglett.0c03241

  日期：2020.11.6

  A chemo- and regioselective perfluoromethylation using thioamides/selenoamides (prepared one step from corresponding lactams) as starting materials has been discovered. The reaction demonstrated complementary chemoselectivity to the C-H trifluoromethylation of (hetero)arenes as well as remarkable functional group compatibility especially toward radical sensitive olefin-, alkyne-, and arylhalide-bearing substrates. The examples of perfluorothio-/selenolated drug molecules indicated application potential of this strategy in drug modification and drug-analogue preparation.