1,3-Dithiane
(Synonyms: 1,3-二噻烷) 目录号 : GC60011
1,3-二噻烷2位的亚甲基氢具有较高的酸度（pKa31.1），在烷基锂等强碱作用下可生成烷基阴离子物种。由于硫缩醛通过脱保护转化为羰基，1,3-二噻烷可用作酰基阴离子等价物（酰基极性改变）。也就是说，酮醛可以通过使亲核试剂如卤代烷反应然后将产物水解来获得。它也可以通过脱硫反应转化为烷烃。
Cas No.:505-23-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
1,3-Dithiane is a protected formaldehyde anion equivalent that could serve as a useful labeled synthon[1]. 1,3-Dithiane is also a sulfur-containing Maillard reaction products (MRPs) found in boiled beef extracts. 1,3-Dithiane shows a potent direct-acting mutagenicity toward S. typhimurium TA98 and TA100[2].
[1]. Lee H, et al. Genotoxicity of 1,3-dithiane and 1,4-dithiane in the CHO/SCE assay and the Salmonella/microsomal test. Mutat Res. 1994 Jun;321(4):213-8. [2]. Martinez RA, et al. Synthesis of isotopically labeled 1,3-dithiane. J Labelled Comp Radiopharm. 2014 May 15;57(5):338-41.
| Cas No. | 505-23-7 | SDF | |
| 别名 | 1,3-二噻烷 | ||
| Canonical SMILES | S1CSCCC1 | ||
| 分子式 | C4H8S2 | 分子量 | 120.24 |
| 溶解度 | DMSO : 100 mg/mL (831.67 mM; Need ultrasonic) | 储存条件 | 4°C, stored under nitroge |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 8.3167 mL | 41.5835 mL | 83.167 mL |
| 5 mM | 1.6633 mL | 8.3167 mL | 16.6334 mL |
| 10 mM | 0.8317 mL | 4.1583 mL | 8.3167 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
2-Methyl-2-(3-nitro-phen-yl)-1,3-dithiane
Acta Crystallogr Sect E Struct Rep Online 2012 Jun 1;68(Pt 6):o1827.PMID:22719599DOI:10.1107/S1600536812022283.
The title compound, C(11)H(13)NO(2)S(2), contains a 1,3-Dithiane ring in an almost ideal chair conformation with the following puckering parameters: Q = 0.7252 (15) Å, θ = 6.71 (13) and ϕ = 50.4 (11)°. The benzene ring occupies an axial position at the dithiane ring. The nitro group is almost coplanar with the benzene ring [O-N-C-C = -3.2 (2)°]. The mol-ecule has an L-shape with a C-C-C-C torsion angle of -74.15 (17)° for the atoms of the methyl group and the dithiane-benzene linkage. The crystal packing is stabilized only via weak non-specific van der Waals inter-actions.
7-Nitro-1,2,3,4-tetra-hydro-naphthalene-1-spiro-2'-(1,3-Dithiane)
Acta Crystallogr Sect E Struct Rep Online 2009 Jan 17;65(Pt 2):o347.PMID:21581948DOI:10.1107/S1600536809001536.
In the title compound, C(13)H(15)NO(2)S(2), the nitro group is coplanar with the benzene ring to which it is attached, forming a dihedral angle of 1.07 (14)°. The dithiane ring adopts a chair conformation. In the crystal structure, mol-ecules are linked through C-H⋯O and C-H⋯π [C⋯Cg = 3.7164 (15) Å] inter-actions. The crystal studied was an inversion twin with an 0.134 (5):0.866 (5) domain ratio.
2,2'-Ethylenebis(1,3-Dithiane) as a polydentate μ2-, μ4- and μ5-assembling ligand for the construction of sulphur-rich Cu(I), Hg(II) and heterometallic Cu(I)/Hg(II) coordination polymers featuring uncommon network architectures
Dalton Trans 2022 May 17;51(19):7581-7606.PMID:35507431DOI:10.1039/d2dt00800a.
With the aim to elaborate novel and inexpensive sulphur-rich materials featuring unusual network architectures, the coordination chemistry of the tetradentate thiaheterocycle 1,2-di(1,3-dithian-2-yl)ethane L1 ligand toward CuX and HgX2 salts was investigated. When L1 is reacted with CuI in a 1 : 1 ratio, a two-dimensional CP [{Cu(μ2-I)2Cu}(μ2-L1)]n (CP1) is formed, in which two out of four S atoms of L1 remain non-coordinated. Upon treatment of L1 with CuI in a 1 : 2 ratio, [{Cu(μ2-I)2Cu}(μ4-L1)]n (CP2) is obtained, in which each S atom of L1 coordinates to one copper centre forming a 2D layer. Raising the ligand-to-CuI ratio to 1 : 4 affords the 2D material [{Cu(μ4-I)(μ2-I)Cu}2(μ4-L1)]n (CP3), in which [Cu(μ4-I)(μ2-I)Cu]n ribbons are interconnected through μ4-bridging L1 ligands. Upon the reaction of L1 with CuBr in a 1 : 2 ratio, a 2D CP [{Cu(μ2-Br)}2(μ2-L1)(μ4-L1)0.5]n (CP4) is formed at room temperature and a 2D CP [{Cu(μ2-Br)}2(μ4-L1)]n (CP5) is obtained in refluxing propionitrile. In CP4 and CP5 Cu atoms are bridged by a single μ2-Br ligand giving rise to [Cu(μ2-Br)Cu]n ribbons but CP4 differs from CP5 from the metal to ligand ratio and the presence of non-coordinated S atoms. Employing a 1 : 3 ratio, a 1D ribbon [{Cu(μ2-Br)}3(MeCN)(μ4-L1)]n (CP6) is generated, that contains both tetrahedral and trigonal copper atoms. CP6 also presents two different L1 ligands that differ by the coordination mode of the sulphur atoms (S acting as 2 or as 4 electron-donor). With CuCl, a 2D network [{Cu(μ2-Cl)2Cu}(μ4-L1)]n (CP7) is generated. L1 coordinates also on HgX2 salts to yield CPs whose architecture depends on the ligand-to-metal ratio. The meander-shaped 1D CP [(HgI2)(μ2-L1)]n (CP8) and the linear 1D ribbons of CP9 and CP12 [(HgX2)(μ2-L1)]n (X = Br, Cl) result from treatment with L1 in a 1 : 1 ratio. In the case of HgBr2, using a 2 : 1 metal-to-ligand ratio, 1D polymeric [{BrHg(μ2-Br)2HgBr}(μ2-L1)] (CP10) is produced. HgI2 and HgBr2 have also been reacted with 2-methyl-1,3-dithiane L2 yielding the molecular complexes [{IHg(μ2-I)2HgI}(κ1-L2)2] (D1) and [HgBr2(κ1-L2)2] (M1). Two heterometallic 1D materials [{IHg(μ2-I)2HgI(μ2-I)2{Cu(RCN)2}2(μ2-L1)]n (CP13) and (CP14) result from the treatment of CP1 with HgI2 in MeCN or EtCN. Performing the reaction of CP1 with HgBr2 in acetonitrile produces the zwitterionic 2D material [Cu(MeCN)}(HgIBr2)(μ2-L1)1.5]n (CP15).
Polymorphism, Halogen Bonding, and Chalcogen Bonding in the Diiodine Adducts of 1,3- and 1,4-Dithiane
Molecules 2021 Aug 17;26(16):4985.PMID:34443571DOI:10.3390/molecules26164985.
Through variations in reaction solvent and stoichiometry, a series of S-diiodine adducts of 1,3- and 1,4-dithiane were isolated by direct reaction of the dithianes with molecular diiodine in solution. In the case of 1,3-Dithiane, variations in reaction solvent yielded both the equatorial and the axial isomers of S-diiodo-1,3-dithiane, and their solution thermodynamics were further studied via DFT. Additionally, S,S'-bis(diiodo)-1,3-dithiane was also isolated. The 1:1 cocrystal, (1,4-dithiane)·(I2) was further isolated, as well as a new polymorph of S,S'-bis(diiodo)-1,4-dithiane. Each structure showed significant S···I halogen and chalcogen bonding interactions. Further, the product of the diiodine-promoted oxidative addition of acetone to 1,4-dithiane, as well as two new cocrystals of 1,4-dithiane-1,4-dioxide involving hydronium, bromide, and tribromide ions, was isolated.
Genotoxicity of 1,3-Dithiane and 1,4-dithiane in the CHO/SCE assay and the Salmonella/microsomal test
Mutat Res 1994 Jun;321(4):213-8.PMID:7515159DOI:10.1016/0165-1218(94)90072-8.
1,3-Dithiane and 1,4-dithiane are the sulfur-containing Maillard reaction products (MRPs) which have been found in boiled beef extracts. In this study the genotoxicity of these products was examined using the Salmonella/microsomal test and the CHO/SCE assay. 1,3-Dithiane showed a potent direct-acting mutagenicity toward S. typhimurium TA98 and TA100, but 1,4-dithiane had a lower mutagenicity toward both tester strains. Both compounds were shown to be non-mutagenic with hepatic metabolic activation with the exception of 1,3-Dithiane toward strain TA100. To compare the mutagenic potential of 1,3-Dithiane and 1,4-dithiane with other types of MRPs, 24 MRPs were examined for their mutagenicity to S. typhimurium TA98 and TA100 in the presence or absence of S9 mix. 2,6-Dimethylpyrazine, furan, 2-acetylpyrrole, and thiazole were shown to be mutagenic. However, these four MRPs exhibited a lower mutagenicity in TA98 than 1,3-Dithiane and 1,4-dithiane. Furthermore, SCE frequencies in CHO cells were very significantly induced by 1,3-Dithiane in the absence of S9 mix, but the SCE-inducing capability of 1,3-Dithiane was reduced or even disappeared with metabolic activation. 1,4-Dithiane did not significantly induce SCE frequencies in the presence or absence of S9 mix. Thus, we concluded that 1,3-Dithiane was a potent mutagenic MRP in the Salmonella/microsomal test, whereas it was a weak SCE inducer in the CHO/SCE assay.