(o-aminophenylthio)acetonitrile | 62225-57-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (o-aminophenylthio)acetonitrile
• 英文别名: 2-(2-aminophenylthio)acetonitrile；o-amino-S-cyanomethylthiophenol；Acetonitrile, [(2-aminophenyl)thio]-；2-(2-aminophenyl)sulfanylacetonitrile
• CAS: 62225-57-4
• 化学式: C₈H₈N₂S
• 分子量: 164.231
• InChiKey: MNPCKQVFLSQOLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (o-aminophenylthio)acetonitrile 在 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.33h， 生成 4-methoxycarbonyl-4H-1,4-benzothiazine-2-carbonitrile
  参考文献：
  名称：

  EWG稳定的(2-异氰基苯硫基)甲基阴离子闭环合成4H-1,4-苯并噻嗪衍生物的新方法

  摘要：

  2-氰基（苯基亚磺酰基-、对-硝基苯基-或邻-硝基苯基-）甲基苯硫基异氰化物由 2-氨基苯硫醇合成，并显示通过去质子化 2,4-二取代 4H-1,4-苯并噻嗪衍生物进行闭环与硫原子相邻的氢用氢化钠或叔丁醇钾，然后用各种亲电子试剂捕获。

  DOI：

  10.1055/s-2006-926385
• 作为产物：
  描述：

  双(2-硝基苯基)二硫化物 在 盐酸 、 溶剂黄146 、 锌 作用下， 生成 (o-aminophenylthio)acetonitrile
  参考文献：
  名称：

  Bertoglio Riolo, Annali di Chimica, 1955, vol. 45, p. 1174,1176

  摘要：

  DOI：

文献信息

• A Convenient and General Synthesis of 2-Aryl- and 2-Pyridyl-3-oxo-3,4-dihydro-2<i>H</i>-1,4-benzothiazines
  作者：Niels Jacobsen、Hans Kolind-Andersen

  DOI：10.1055/s-1990-27051

  日期：——

  The reaction of bis(2-aminophenyl) disulphide 1 with methyl or ethyl aryl- or pyridylacetates and sodium hydride gives the title compounds in good yield and high purity. The reaction is general, the starting materials easily available and the workup is simple and rapid

  双（2-氨基苯基）二硫化物1与甲基或乙基芳基或吡啶乙酸盐及氢化钠的反应在良好的产率和高纯度下生成该标题化合物。该反应具有通用性，起始材料易于获得，后处理简单快速。
• Studies on 1,4-benzothiazines. I. Synthesis of 2,3-dihydro-3-imino-4H-1,4-benzothiazines and acetylation of the N-methyl derivative.
  作者：HIROSHI HIRANO、MASANORI TAKAMATSU、KAZUAKI SUGIYAMA、TAKUSHI KURIHARA

  DOI：10.1248/cpb.27.374

  日期：——

  o-Amino-S-cyanomethylthiophenol (1) obtained by the reaction of o-aminothiophenol with monochloroacetonitrile was converted to 2, 3-dihydro-3-imino-4H-1, 4-benzothiazine (2). Furthermore, the N-methyl derivative (6) was prepared from o-(formyl-methylamino)-S-cyanomethylthiophenol (5) which was obtained by the reaction of benzothiazolium iodide (4) with monochloroacetonitrile under basic conditions. Acetylation of 6 was attempted. The compound 6 (base) was acetylated with acetic anhydride in pyridine at room temperature to give the acetylimino compound (9) by the usual reaction. Unexpectedly, heating under reflux of the hydrochloride of 6 in acetic anhydride afforded a new ring system compound, 8, 15-diazaphenothiazino [8, 7-h] phenothiazine derivative (10) in fair yield. The last reaction gave a small amount of two by-products, which proved to be o-(acetyl-methylamino)-S-acetylcarbamoylmethylthiophenol (11) and 2, 3-dihydro-4-methyl-4H-1, 4-benzothiazin-3-one (12), respectively.

  由邻氨基苯硫酚与一氯乙腈反应得到的邻氨基-S-氰基甲基苯硫酚（1）被转化为 2，3-二氢-3-亚氨基-4H-1，4-苯并噻嗪（2）。此外，N-甲基衍生物（6）是由邻-（甲酰基-甲基氨基）-S-氰甲基苯硫酚（5）制备的，后者是由苯并噻唑碘化物（4）与一氯乙腈在碱性条件下反应得到的。尝试对 6 进行乙酰化。在室温下，用乙酸酐在吡啶中对化合物 6（碱）进行乙酰化，通过通常的反应得到乙酰亚氨基化合物 (9)。意想不到的是，在乙酸酐中回流加热 6 的盐酸盐，得到了一种新的环系统化合物，8，15-二氮吩噻嗪[8，7-h]吩噻嗪衍生物（10），收率尚可。最后一个反应产生了少量的两种副产物，分别是邻-（乙酰基-甲基氨基）-S-乙酰基氨基甲酰甲基苯硫酚（11）和 2，3-二氢-4-甲基-4H-1，4-苯并噻嗪-3-酮（12）。
• AMIDINE, THIOUREA AND GUANIDINE DERIVATIVES OF 2-AMINOBENZOTHIAZOLES AND AMINOBENZOTHIAZINES FOR THEIR USE AS PHARMACOLOGICAL AGENTS FOR THE TREATMENT OF NEURODEGENERATIVE PATHOLOGIES
  申请人：Anzini Maurizio

  公开号：US20100197670A1

  公开（公告）日：2010-08-05

  Amidine, thiourea and guanidine derivatives of appropriately substituted 2-aminobenzothiazoles, 2-amino-3,1-4H-benzothiazines and 3-amino-1,4-3H-benzothiazines, as understood from formula (I), the related pharmaceutically acceptable salts and solvates thereof: and the use of the products and the corresponding pharmaceutical formulations for the treatment of neurodegenerative pathologies such as cerebral ischemia, neurodegeneration induced by cranial trauma, Alzheimer's disease, Multiple Sclerosis and Amyotrophic Lateral Sclerosis.

  适当取代的2-氨基苯并噻唑、2-氨基-3,1-4H-苯并噻嗪和3-氨基-1,4-3H-苯并噻嗪的脲、硫脲和胍衍生物，如公式（I）所示，相关的药用可接受盐和溶剂合物：以及所述产品和相应的制药配方用于治疗神经退行性病理，如脑缺血、颅脑创伤引起的神经退化、阿尔茨海默病、多发性硬化症和肌萎缩侧索硬化症。
• Synthesis of fused 1,2,4-thiadiazoles from 5-chloro-1,2,4-thiadiazol-3(2H)-ones
  作者：Gerrit L'abbé、Johan Buelens、Wim Dehaen、Suzanne Toppet、Janine Feneau-Dupont、Jean-Paul Declercq

  DOI：10.1016/s0040-4020(01)85231-5

  日期：1994.1

  Fused 1,2,4-thiadiazoles (14-18 and 26-31) are conveniently prepared by reacting the chlorothiadiazolone 12 with omega-aminonitriles and aminoazoles. During these reactions the original thiadiazole ring is opened and a new, fused thiadiazole rig is formed, probably via a hypervalent sulfur intermediate. The products derived from the aminoazoles were analyzed by X-ray crystallography and found to have structures different from those published earlier.(7)
• Synthesis of fused 1,2,4-thiadiazoles from ω-amino nitriles and thioacyl isothiocyanates
  作者：Gerrit L'abbé、Bart D'hooge、Wim Dehaen

  DOI：10.1039/p19960000225

  日期：——

  Fused 1,2,4-thiadiazoles can be prepared in high yields from cyano substituted amines and thiocarbamoyl isothiocyanates by oxidation of the intermediate dithiobiurets.