5-methylsulfanyl-4(4-trifluoromethylbenzoyl)-1,2,3-thiadiazole | 1428878-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methylsulfanyl-4(4-trifluoromethylbenzoyl)-1,2,3-thiadiazole
• 英文别名: (5-Methylsulfanylthiadiazol-4-yl)-[4-(trifluoromethyl)phenyl]methanone；(5-methylsulfanylthiadiazol-4-yl)-[4-(trifluoromethyl)phenyl]methanone
• CAS: 1428878-91-4
• 化学式: C₁₁H₇F₃N₂OS₂
• 分子量: 304.317
• InChiKey: VPDVIBHLVHKQGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 3-hydroxy-3-(4-(trifluoromethyl)phenyl)prop-2-enedithioate 在 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 5-methylsulfanyl-4(4-trifluoromethylbenzoyl)-1,2,3-thiadiazole
  参考文献：
  名称：

  通过一锅中的亚硝化/还原/重氮化/环化级联反应从α-烯丙基二硫代酯轻松而直接地合成1,2,3-噻二唑

  摘要：

  通过一锅中通过级联1 –形成亚硝化/还原/重氮化/环化的顺序，可以从α-烯丙基二硫代酯中合成出操作简单，经济，直接的多种4,5-二取代的1,2,3-噻二唑。 2（N–S）和3–4（C–N）键。重要的是，这是来自二硫代酯的高度官能化的1,2,3-噻二唑的第一个直接方法。

  DOI：

  10.1016/j.tetlet.2014.02.115

文献信息

• Eco-efficient, regioselective and rapid access to 4,5-disubstituted 1,2,3-thiadiazoles via [3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide under solvent-free conditions
  作者：Maya Shankar Singh、Anugula Nagaraju、Girijesh Kumar Verma、Gaurav Shukla、Rajiv Kumar Verma、Abhijeet Srivastava、Keshav Raghuvanshi

  DOI：10.1039/c3gc37047j

  日期：——

  An efficient, sustainable, and regioselective one-pot synthesis of hitherto unreported 4-aroyl/hetaroyl/alkanoyl-5-alkyl/allyl/benzylsulfanyl-1,2,3-thiadiazoles has been achieved by [3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide through cascade 1–2 (S–N) and 3–4 (C–N) bond connections involving Wolff-type heterocyclization. Optimally, the reactions are very fast and completed within 2–15 minutes, when a mixture of α-enolicdithioester and tosyl azide was stirred at 0 °C in the presence of Et3N under solvent-free conditions. Furthermore, no co-catalyst or activator is necessary. The eco-compatibility, mild conditions, excellent yields, easy purification, and avoidance of expensive/toxic reagents are advantages of this protocol to access this medicinally privileged substructure.

  通过 α 的 [3 + 2] 环加成，实现了迄今为止未报道的 4-芳酰基/杂酰基/烷酰基-5-烷基/烯丙基/苄基硫基-1,2,3-噻二唑的高效、可持续和区域选择性一锅法合成-烯醇二硫酯与甲苯磺酰叠氮通过级联 1–2 (S–N) 和 3–4 (C–N) 键连接，涉及 Wolff 型杂环化。最理想的是，当α-烯醇二硫酯和甲苯磺酰叠氮化物的混合物在无溶剂条件下、Et3N存在下于0℃搅拌时，反应非常快并在2-15分钟内完成。此外，不需要助催化剂或活化剂。生态相容性、温和的条件、优异的产量、易于纯化和避免昂贵/有毒试剂是该协议获得这种医学上特权子结构的优点。
• A facile and straightforward synthesis of 1,2,3-thiadiazoles from α-enolicdithioesters via nitrosation/reduction/diazotization/cyclization cascade in one-pot
  作者：Anugula Nagaraju、B. Janaki Ramulu、Gaurav Shukla、Abhijeet Srivastava、Girijesh Kumar Verma、Keshav Raghuvanshi、Maya Shankar Singh

  DOI：10.1016/j.tetlet.2014.02.115

  日期：2014.4

  operationally simple, economical, and straightforward synthesis of diverse 4,5-disubstituted 1,2,3-thiadiazoles from α-enolicdithioesters has been achieved via nitrosation/reduction/diazotization/cyclization sequence in one-pot through the formation of cascade 1–2 (N–S) and 3–4 (C–N) bonds. Importantly, this is the first straightforward entry to highly functionalized 1,2,3-thiadiazoles from dithioesters

  通过一锅中通过级联1 –形成亚硝化/还原/重氮化/环化的顺序，可以从α-烯丙基二硫代酯中合成出操作简单，经济，直接的多种4,5-二取代的1,2,3-噻二唑。 2（N–S）和3–4（C–N）键。重要的是，这是来自二硫代酯的高度官能化的1,2,3-噻二唑的第一个直接方法。
• Visible light promoted synthesis of disubstituted 1,2,3-thiadiazoles
  作者：Vishal SRIVASTAVA、Pravin K. SINGH、Praveen P. SINGH

  DOI：10.33224/rrch.2020.65.3.01

  日期：——

  A novel one-pot visible light irradiated synthesis of disubstituted 1,2,3-thiadiazole from alpha-enolicdithioesters with tosyl azide have been reported. The reaction completed within 12-20 minutes, at room temperature, when a mixture of alpha-enolicdithioester and tosyl azide undergo photocatalysed reaction under solvent-free conditions. Furthermore, no co-catalyst or activator is necessary. This protocol includes eco-compatibility, mild conditions, excellent yields, easy purification, and avoidance of expensive/toxic reagents to synthesise organic compounds of medicinal importance, which fulfils the basic principle of green chemistry.