1,2-dithiolo<5,4-b>pyridin-3-one | 65282-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1,2-dithiolo<5,4-b>pyridin-3-one
• 英文别名: 1,2-Dithiolo(3,4-b)pyridin-3-one；dithiolo[3,4-b]pyridin-3-one
• CAS: 65282-42-0
• 化学式: C₆H₃NOS₂
• 分子量: 169.228
• InChiKey: ZFEQZSUEICITLV-UHFFFAOYSA-N

物化性质

• 熔点：
  97-99 °C(Solv: ethanol (64-17-5))
• 沸点：
  383.3±34.0 °C(Predicted)
• 密度：
  1.578±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-dithiolo<5,4-b>pyridin-3-one 在 碘 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 2-(p-chlorobenzyl)isothiazolo<5,4-b>pyridin-3-one
  参考文献：
  名称：

  Baggaley, Keith H.; Jennings, L. John A.; Tyrrell, A. William R., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1393 - 1396

  摘要：

  DOI：
• 作为产物：
  描述：

  2-巯基烟酸 在 tetraphosphorus decasulfide 、 mercury(II) diacetate 作用下， 以 吡啶 、 氯仿 、 溶剂黄146 为溶剂， 反应 74.0h， 生成 1,2-dithiolo<5,4-b>pyridin-3-one
  参考文献：
  名称：

  Baggaley, Keith H.; Jennings, L. John A.; Tyrrell, A. William R., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1393 - 1396

  摘要：

  DOI：

文献信息

• Synthesis of 6,7-Dihydropyrrolo[2,1-<i>c</i> ][1,3]thiazino[3,2-<i>a</i> ]pyrazine-4(11b<i>H</i> )-(thi)ones from 1,2-Dithiolo-3-(thi)ones
  作者：Vladimir A. Ogurtsov、Yury V. Karpychev、Yulia V. Nelyubina、Petr V. Primakov、Panayiotis A. Koutentis、Oleg A. Rakitin

  DOI：10.1002/ejoc.201900142

  日期：2019.7.14

  Both monocyclic and fused 1,2‐di‐thiolo‐3‐(thi)ones underwent addition of 3,4‐dihydropyrrolo[1,2‐a]pyrazine with selective extrusion of S2 atom and formation of 6,7‐dihydropyrrolo[2,1‐c][1,3]thi‐azino[3,2‐a]pyrazine‐4(11bH)‐(thi)ones. 1,2‐Dithiolo‐3‐one moiety was found more reactive than the corresponding 1,2‐dithiole‐3‐thione one.

  单环和稠合的1,2-二硫代3-（thi）酮都加入了3,4-二氢吡咯并[1,2- a ]吡嗪，并选择性挤出了S2原子并形成了6,7-二氢吡咯并[2] ，1‐ c ] [1,3]噻嗪[3,2‐ a ]吡嗪‐4（11b H）‐（噻吩）酮。发现1,2-二硫代-3-酮比相应的1,2-二硫代-3-硫酮具有更高的反应活性。
• 一种苯并二硫杂环戊烯类骨架化合物的制备 方法
  申请人：江苏师范大学

  公开号：CN110950836B

  公开（公告）日：2022-04-05

  本发明公开了一种苯并二硫杂环戊烯类骨架化合物的制备方法，将2‑溴硫代苯甲酰胺衍生物和S8加入有机溶剂中，再加入配体和碱，惰性气氛中在铜催化剂作用下反应，然后将反应体系经抽滤和酸性水解处理，即得。本发明具有操作简单，原料和试剂易得，条件温和，反应体系绿色环保，产物易分离纯化的优点，适用于合成多种苯并二硫杂环戊烯类骨架化合物，特别适用于大规模的工业生产，可以高效、高收率地制得高纯度的苯并二硫杂环戊烯类骨架化合物，产物收率最高可达91％。
• Synthesis and in Vitro Anti<i>-Mycobacterium </i>Activity of <i>N</i>-Alkyl-1,2-dihydro-2-thioxo-3-pyridinecarbothioamides. Preliminary Toxicity and Pharmacokinetic Evaluation
  作者：Giuseppe Pagani、Massimo Pregnolato、Daniela Ubiali、Marco Terreni、Claudio Piersimoni、Francesco Scaglione、Franco Fraschini、Alicia Rodríguez Gascón、José Luis Pedraz Muñoz

  DOI：10.1021/jm991044p

  日期：2000.1.1

  Disseminated infections with Mycobacterium tuberculosis (MT) and Mycobacterium avium complex (MAC) are increasingly opportunistic diseases in patients with advanced acquired human immunodeficiency syndrome (AIDS). A series of N-alkyl-1,2-dihydro-2-thioxo-3-pyridinecarbothioamides has been synthesized, and MICs for MT and MAC strains, either standard or isolated from infected patients, have been determined. Preliminary tests show a good activity and a very low toxicity for some derivatives. Pharmacokinetic studies in the rat show a very rapid elimination from the body after intravenous administration and a poor absorption after oral administration.
• 1,2-Dithiolan-3-ones and derivatives structurally related to leinamycin. Synthesis and biological evaluation
  作者：Raul Salvetti、Giovanni Martinetti、Daniela Ubiali、Massimo Pregnolato、Giuseppe Pagani

  DOI：10.1016/s0014-827x(03)00134-4

  日期：2003.9

  Leinamycin, an antitumor antibiotic isolated from Streptomyces sp., shows a 1,2-dithiolan-3-one 1-oxide heterocycle that appears to be involved in the biological activity. Several derivatives related to 1,2-dithiolan-3-one 1-oxide have been prepared and their activity as antineoplastic agents have been investigated. The synthesized compounds did not display a significative antitumor or cytotoxic activity in vitro.
• New 5-Substituted Derivatives of Ethyl 2,3-Dihydro-3-oxoisothiazolo[5,4-b]pyridine-2-acetate
  作者：Victor Martinez-Merino、Maria J. Gil、Alberto Gonzalez、Jose M. Zabalza、Javier Navarro、Maria A. Ma勃

  DOI：10.3987/com-93-6556

  日期：——

  New series of ethyl 5-substituted 2,3-dihydro-3-oxoisothiazolo[5,4-b] pyridine-2-acetate was prepared either a) directly by reaction of 5-substituted 2-chlorothio-3-pyridinecarbonyl chlorides with ethyl glycinate or b) by oxidation of the correspondent 2-mercapto-3-pyridinecarboxamides. New 5-substituted 1,2-dihydro-2-thioxo-3-pyridinecarboxylic acids as starting materials are described.