2-phenyl-4-diethylammino-1,4,2,5-dithiazine | 118535-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-4-diethylammino-1,4,2,5-dithiazine
• 英文别名: N,N-diethyl-6-phenyl-1,4,2,5-dithiadiazin-3-amine
• CAS: 118535-45-8
• 化学式: C₁₂H₁₅N₃S₂
• 分子量: 265.403
• InChiKey: JGOHIUPYIOWQQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  decamethylrhenocene 、 2-phenyl-4-diethylammino-1,4,2,5-dithiazine 以 苯 为溶剂， 以6.4%的产率得到(η(5)-cyclopentadienyl)(1-phenylmethanimine-N,1-dithiolato)cobalt(III)
  参考文献：
  名称：

  A novel metallacycle, 1,2,5,3-cobaltadithiazole. Formation, structure, and properties of (η5-cyclopentadienyl or η5 pentamethylcyclopentadienyl)(1-phenylmethanimine-N,1l-dithiolato) - cobalt(III)

  摘要：

  (Eta5-Cyclopentadienyl)(1-phenylmethanimine-N,1-dithiolato)cobalt(III), [Co(eta5-C5R5){SNC(Ph)S}] (1a: R=H or 1b: R=CH3), which contain a 1,2,5,3-cobaltadithiazole ring were synthesized in the reactions of [Co(eta5-C5R5)Ln] (Ln = (CO)2 or 1,5-cyclooctadiene) with two types of heterocyclic compounds: (1) compounds with a partial structure of -S-N=C(Ph)-S- or with similar structures; and (2) compounds which give benzonitrile sulfide on thermolysis or photolysis. The crystals of 1b are orthorhombic of space group P2,2,2 with a = 14.936 angstrom, b = 14.262 angstrom, c = 8.078 angstrom and Z = 4. The structure was solved and refined to R = 0.038 and R(w) = 0.040 by using 3981 independent reflections. The structure of 1,2,5,3-cobaltadithiazole is similar to that of 1,2,5-cobaltadithiolenes. The 1,2,5,3-cobaltadithiazole ring is almost planar and perpendicular to cp*. The cobaltadithiazoles undergo a reversible one electron reduction which is ascribed to the process from Co(III) to Coll. The halfwave potential of -1.34 V versus Ag \0.1 mol dm-3 AgClO4 for the reduction of 1b is less negative than that of the cobaltadithiolene with a similar structure. This shows that the nitrogen atom in the ring attracts electrons and causes the cobaltadithiazole ring to be electron-deficient.

  DOI：

  10.1016/0022-328x(94)80132-0
• 作为产物：
  描述：

  [5-(diethylamino)-3-phenyl-1λ4,4-dithia-2-azacyclopenta-2,5-dien-1-yl] perchlorate 生成 2-phenyl-4-diethylammino-1,4,2,5-dithiazine
  参考文献：
  名称：

  JONEHMOTO, KATSUMI;SIBUYA, ISAO

  摘要：

  DOI：

文献信息

• Formation of 1,4,2,5-Dithiadiazines as a Heterocyclic System by Reaction of 1,4,2-Dithiazolium Salts with Sulfenamides
  作者：Katsumi Yonemoto、Isao Shibuya、Kazumasa Honda

  DOI：10.1246/bcsj.61.2232

  日期：1988.6

  application of sulfenamides for ring expansion on nitrogen atom has been reported to give 1,4,2,5-dithiadiazines (3) from 1,4,2-dithiazolium salts (1). The structure of 3 was confirmed by X-ray crystallographic analysis. The similar ring expansion reaction occurred on 1,3-dithiolium salts (5) to afford 1,4,2-dithiazines (6).

  据报道，使用次磺酰胺在氮原子上扩环的第一个例子是从 1,4,2-二噻唑鎓盐 (1) 得到 1,4,2,5-二噻二嗪 (3)。通过X射线晶体学分析证实了3的结构。类似的扩环反应发生在 1,3-二硫鎓盐 (5) 上，得到 1,4,2-二噻嗪 (6)。
• Ring Expansion Reaction of Heterocyclic Cation Compounds by Incorporating One Nitrogen Atom Using I₂–NH₃System
  作者：Katsumi Yonemoto、Isao Shibuya

  DOI：10.1246/cl.1989.89

  日期：1989.1

  The reaction of various heterocyclic cation compounds with I2/NH4OH resulted in ring expansion on nitrogen atom. The similar ring expansion reaction occurred on the corresponding triiodides with NH4OH. The reaction mechanism based on initial nucleophilic attack of NH3 on cations, subsequent oxidative iodination, and liberation of I− is proposed.

  各种杂环阳离子化合物与 I2/NH4OH 的反应导致氮原子上的环膨胀。类似的扩环反应发生在相应的三碘化物与 NH4OH 上。提出了基于 NH3 对阳离子的初始亲核攻击、随后的氧化碘化和 I- 释放的反应机制。
• Decomposition Reaction of 3-Aryl-6-disubstituted Amino-1,4,2,5-dithiadiazines in the Solid State
  作者：Katsumi Yonemoto、Isao Shibuya

  DOI：10.1246/bcsj.62.2407

  日期：1989.7

  3-Diethylamino-6-phenyl-1,4,2,5-dithiadiazine, on standing in air at room temperature, decomposed to afford 5-diethylamino-3-phenyl- and 3,5-bis(diethylamino)-1,2,4-thiadiazoles, whereas in the melt and in solution it was remarkably stable. With increasing bulkiness of substituents (Ar and/or NR2) in 1,4,2,5-dithiadiazines, their stability in the solid state clearly enhanced. Some interstack interactions in the crystal seem to favor the decomposition.

  3-二乙氨基-6-苯基-1,4,2,5-二噻二嗪在室温下置于空气中会分解生成 5-二乙氨基-3-苯基和 3,5-双（二乙基氨基）-1,2,4-噻二唑，而在熔体和溶液中则非常稳定。随着 1,4,2,5-二噻二唑中取代基（Ar 和/或 NR2）体积的增加，它们在固态中的稳定性明显增强。晶体中的一些堆间相互作用似乎有利于其分解。
• YONEMOTO, KATSUMI;SHIBUYA, ISAO, CHEM. LETT.,(1989) N, C. 89-90
  作者：YONEMOTO, KATSUMI、SHIBUYA, ISAO

  DOI：——

  日期：——
• JONEHMOTO, KATSUMI;SIBUYA, ISAO
  作者：JONEHMOTO, KATSUMI、SIBUYA, ISAO

  DOI：——

  日期：——