| 1428878-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1428878-77-6
• 化学式: C₁₃H₁₄OS₂
• 分子量: 250.386
• InChiKey: FTHUNVZROHBBAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以86%的产率得到2-hydroxyimino-3-oxo-3-p-tolyl-dithiopropionic acid allyl ester
  参考文献：
  名称：

  Easy access to α-hydroxyimino-β-oxodithioesters and application towards the synthesis of diverse 1,4-thiazine-3-ones via reduction/annulation cascade

  摘要：

  An operationally simple and facile synthesis of alpha-hydroxyimino-beta-oxodithioesters has been achieved by nitrosation of alpha-enolicdithioesters. They were further treated with internal alkynes to afford diverse 1,4-thiazin-3-ones via domino reduction/annulation strategy under mild reaction conditions. Importantly, this is the first straightforward entry to highly functionalized 1,4-thiazin-3-one derivatives from simple starting materials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.097

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。