3-甲基-1,3-苯并噻唑-2-硒酮 | 2786-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 3-甲基-1,3-苯并噻唑-2-硒酮
• 中文别名: 2-硒代-3-甲基苯并噻唑
• 英文名称: 3-methylbenzothiazole-2-selone
• 英文别名: N-methylbenzothiazole-2-selone；3-Methylbenzothiazole-2(3H)-selone；3-methyl-1,3-benzothiazole-2-selone
• CAS: 2786-43-8
• 化学式: C₈H₇NSSe
• 分子量: 228.176
• InChiKey: VBKDUIRAXCKPOA-UHFFFAOYSA-N

物化性质

• 熔点：
  108-110 °C(Solv: ethanol (64-17-5))
• 沸点：
  328.4±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1(b)
• 海关编码：
  2934999090
• 危险品运输编号：
  UN 3282

反应信息

• 作为反应物：
  描述：

  3-甲基-1,3-苯并噻唑-2-硒酮 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以47%的产率得到N-methylbenzothiazole-2-selone dichloride
  参考文献：
  名称：

  The reaction of N-methylbenzothiazole-2-selone and 1,1-dimethylselenourea with sulfuryl chloride and dichlorine †

  摘要：

  研究了 N-甲基苯并噻唑-2-selone (mbts) 和 1,1-二甲基硒脲 (dmsu) 与二氯和氯化剂 SO2Cl2 的反应。在1-1反应中，获得了1-1硒酰胺·Cl2加合物形成的光谱证据；不幸的是，迄今为止结晶尝试尚未成功。然而，对 mbts 与一当量 SO2Cl2 反应产生的离子次要产物进行了单晶 X 射线衍射。当两当量的 SO2Cl2 或过量的二氯气体用 mbts 或 dmsu 处理时，得到各种离子产物，其确切性质取决于所使用的氯化剂、硒代酰胺的特性和反应物的化学计量。 。因此，反应很复杂，并且在大多数情况下，从给定的反应中可以获得多种产物。这项研究代表了首次报道的硒酰胺与氯化剂的反应，并且首次对两种新的硒-氯二元阴离子进行了晶体学表征，即Se2Cl42-和SeCl62-。

  DOI：

  10.1039/a905552e
• 作为产物：
  描述：

  (2Z)-3-甲基-2-(3-甲基-1,3-苯并噻唑-2-亚基)-1,3-苯并噻唑 在 selenium 作用下， 生成 3-甲基-1,3-苯并噻唑-2-硒酮
  参考文献：
  名称：

  Metzger,J. et al., Bulletin de la Societe Chimique de France, 1964, p. 2857 - 2867

  摘要：

  DOI：
• 作为试剂：
  描述：

  苯乙醇 、 丙酸 在 N,N-二甲基苯胺 3-甲基-1,3-苯并噻唑-2-硒酮 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以44%的产率得到丙酸-2-苯乙酯
  参考文献：
  名称：

  INTERMOLECULAR DEHYDRATION BETWEEN CARBOXYLIC ACIDS AND ALCOHOLS BY THE USE OF DIETHYL AZODICARBOXYLATE AND 3-METHYLBENZOTHIAZOLE-2-SELONE

  摘要：

  在二乙基偶氮二羧酸酯和3-甲基苯并噻唑-2-硒酮存在下，羧酸与醇的反应生成相应的酯，并保持醇碳原子的构型。

  DOI：

  10.1246/cl.1984.855

文献信息

• Reaction of dimethylselenourea and selenourea with dibromine to produce selenourea–dibromine, the ‘T’-shaped 1:1 molecular adduct N,N-dimethyl-2-selenourea–dibromine, its solvent of crystallisation-containing analogue and the unusual ionic compound 5[(H2N)(Me2N)CBr]+[SeBr6]2−[Se2Br9]−2[Br3]−. A low temperature crystallographic reinvestigation of N-methylbenzothiazole-2-selone–dibromine
  作者：Philip D. Boyle、Wendy I. Cross、Stephen M. Godfrey、Charles A. McAuliffe、Robin G. Pritchard、Simon J. Teat

  DOI：10.1039/a903564h

  日期：——

  The reactions of the selenoamides N,N-dimethyl-2-selenourea, dmsu, selenourea, su and N-methylbenzothiazole-2-selone, mbts, with dibromine has been studied. In all reactions the bulk product formed is the 1∶1 T-shaped addition compound, selenoamide·Br2. The crystal structure of dmsu·Br2 1 has been determined and compared to its solvated analogue, dmsu·Br2·CH2Cl2. Despite the different crystal packing in these two adducts, an asymmetry in d(Se–Br) is exhibited by both, ruling out the possibility that differences in Se–Br bond lengths are attributed solely to crystal packing forces. Both structures are essentially zwitterionic, a negative charge resides on the SeBr2 moiety and the positive charge is supported by the two nitrogen atoms. The recently reported mbts·Br2, previously described as a carbene interacting with SeBr2, was reinvestigated. Considering findings from a low temperature X-ray study and the 13C NMR spectrum, this compound is in fact also best described as zwitterionic, analogous to 1 and previously described structures. An interesting minor product from the reaction of two equivalents of dibromine with dmsu has also been characterised crystallographically. This complicated ionic structure of formula 5[(H2N)(Me2N)CBr]+[SeBr6]2–[Se2Br9]–2[Br3]– illustrates the susceptibility of certain selenoamides to carbon–selenium bond cleavage when a dihalogen that is more strongly oxidising than I2 or IBr is treated with them in a stoichiometric ratio greater than 1∶1. This curious (and disordered) structure represents the first report of the anion [Se2Br9]–.

  研究了硒酰胺N,N-二甲基-2-硒脲、dmsu、硒脲、su和N-甲基苯并噻唑-2-硒酮、mbts与二溴的反应。在所有反应中，生成的主要产物是1∙1 T形加成化合物硒酰胺·Br2。已确定dmsu·Br2 1的晶体结构，并将其与溶剂化类似物dmsu·Br2·CH2Cl2进行了比较。尽管这两种加合物具有不同的晶体堆积，但两者都表现出d(Se-Br)的不对称性，排除了Se-Br键长差异仅归因于晶体堆积力的可能性。这两种结构基本上都是两性离子，负电荷位于SeBr2部分，正电荷由两个氮原子支撑。最近报道的mbts·Br2（以前描述为与SeBr2相互作用的羰基）被重新研究。考虑到低温X射线研究和13C NMR光谱的结果，实际上，这种化合物最好也描述为两性离子，类似于1和以前描述的结构。还通过晶体学方法表征了二溴与dmsu反应产生的一种有趣的小产物。这种复杂的离子结构，其化学式为5[(H2N)(Me2N)CBr]+[SeBr6]2∙[Se2Br9]∙2[Br3]，
• Compounds containing sulphur chromophores. Part I. The action of bases on heterocyclic sulphide quarternary salts
  作者：Edward B. Knott

  DOI：10.1039/jr9550000916

  日期：——
• The reactions of SbX3 (X=Cl, Br, I) with N-methylbenzothiazole-2-thione (mbtt) and N-methylbenzothiazole-2-selone (mbts). Formation of the mixed mer/fac-complex [mer-SbBr3(mbts)2(μ-mbts)fac-SbBr3(mbts)2]·CH2Cl2
  作者：Nicholas A. Barnes、Stephen M. Godfrey、Robin G. Pritchard、Shane Ratcliffe

  DOI：10.1016/j.poly.2010.02.029

  日期：2010.5

  The reactions of the antimony(III) halides, SbX3 (X = Cl, Br, I) with the heterocyclic thione, N-methylbenzothiazole-2-thione (mbtt) and the analogous selone, N-methylbenzothiazole-2-selone (mbts) are reported. The products formed are highly dependent upon the identity of the halide, and in one case on the identity of the chalcogen donor atom. The reaction of SbCl3 with both mbtt and mbts (and the reaction of SbBr3 with mbtt), forms complexes in CH2Cl2 with a 2:1 ligand to metal ratio, [SbX3(L)(mu-L)(2)SbX3(L)]center dot CH2Cl2, [X = Cl, L = mbtt (1), L = mbts (2); X = Br, L = mbtt (3)]. These complexes are weakly held together, and feature a primary pyramidal SbX3 coordination sphere with weak secondary donor-acceptor bonding to the chalcone donor ligands, giving an overall [3+3] octahedral geometry around each antimony atom. In contrast, the reaction of SbBr3 with mbts in CH2Cl2 produces a highly unusual 5:2 ligand:SbBr3 complex, [mer-SbBr3(mbts)(2)(-mbts)fac-SbBr3(mbts)(2)]center dot CH2Cl2 (4). The fac-substituted antimony center has a [4+2] bonding arrangement, consisting of a primary [SbBr3(mbts)] coordination sphere and weaker secondary bonds to two further mbts ligands. In contrast, the bonding at the mer-substituted antimony atom is better described as [5+1], with a primary [SbBr3(mbts)(2)] coordination sphere and only one secondary bond to another mbts ligand. The complex is highly unusual in featuring two antimony atoms with different primary/secondary coordination spheres in the same complex. The reactions of mbtt and mbts with Sbl(3) result in the formation of 1:1 complexes [SbI3L], which display chain polymeric structures, [SbI2(mbtt)(mu-I)]}(n) (5) and [SbI2(mbts)(mu-I)]}(n) (6). The complexes consist of see-saw [SbI3L] units linked into polymeric chains by bridging iodine atoms, the antimony atoms thus exhibits a square pyramidal geometry. The iodide complexes feature a stereochemically active lone pair trans to the apical iodine atom, and feature much shorter antimony-chalcogen bonds than observed for 1-4. (C) 2010 Elsevier Ltd. All rights reserved.
• Cristiani, Franco; Devillanova, Francesco A.; Diaz, Angelo, Journal of the Chemical Society. Perkin transactions II, 1984, # 8, p. 1383 - 1386
  作者：Cristiani, Franco、Devillanova, Francesco A.、Diaz, Angelo、Verani, Gaetano

  DOI：——

  日期：——
• MITSUNOBU, OYO;TAKEMASA, AKIRA;ENDO, RYOSUKE, CHEM. LETT., 1984, N 6, 855-858
  作者：MITSUNOBU, OYO、TAKEMASA, AKIRA、ENDO, RYOSUKE

  DOI：——

  日期：——