噻吩-2-硫醇钠 | 88048-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 噻吩-2-硫醇钠
• 英文名称: sodium thiophene-2-thiolate
• 英文别名: Sodium;thiophene-2-thiolate
• CAS: 88048-79-7
• 化学式: C₄H₃S₂*Na
• 分子量: 138.19
• InChiKey: BKMBOPMJVDAWPZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.34
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-1-phenyl-ethanone oxime 、 噻吩-2-硫醇钠 在 L-乳酸 、 氯化胆碱 、 碳酸氢钠 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以88%的产率得到(Z)-2-(thiophen-2-ylthio)acetophenone oxime
  参考文献：
  名称：

  Solvent-catalyzed umpolung carbon sulfur bond-forming reactions by nucleophilic addition of thiolate and sulfinate ions to in situ–derived nitrosoalkenes in deep eutectic solvents

  摘要：

  摘要 乳酸和胆碱氯化物形成的低转化温度混合物，在α-氯肟α位形成碳硫键反位有效。脂肪族、芳香族及杂芳香族硫醇盐和亚磺酸盐离子可以顺利地与原位衍生亚硝基烯烃加成，分别得到相应的亚硫酰化或磺酰化加合物，产率非常良好（高达>98%）。该方法具有在室温及空气中进行、使用可生物降解、成本效益反应混合物的优势，既可用作溶剂，也可作为催化剂（20mol%），从而避免了使用无水、危险的易挥发有机溶剂及无气气氛。 补充材料： 本文的补充材料单独提供了一个文件：mmc1.pdf &

  DOI：

  10.1016/j.crci.2017.01.008

文献信息

• Relative Binding Affinity of Thiolate, Imidazolate, Phenoxide, and Nitrite Toward the {Fe(NO)₂} Motif of Dinitrosyl Iron Complexes (DNICs): The Characteristic Pre-Edge Energy of {Fe(NO)₂}⁹ DNICs
  作者：Ming-Che Tsai、Fu-Te Tsai、Tsai-Te Lu、Ming-Li Tsai、Yin-Ching Wei、I-Jui Hsu、Jyh-Fu Lee、Wen-Feng Liaw

  DOI：10.1021/ic901675p

  日期：2009.10.5

  within the range of 7113.4−7113.8 eV for the anionic Fe(NO)2}9 DNICs, implicate that the iron metal center of DNICs is tailored to minimize the electronic changes accompanying changes in coordinated ligands. Our results bridging the ligand-substitution reaction study and X-ray absorption spectroscopy study of the electronic richness of the Fe(NO)2}9 core may point the way to understanding the reasons

  阴离子Fe（NO）2 } 9二亚硝酰基铁络合物（DNIC）[（NO）2 Fe（ONO）2 ] -（1），[（NO）2 Fe（OPh）2 ] -（2），[（NO）2 Fe（OPh）（C 3 H 3 N 2）] -（3）（C 3 H 3 N 2 =咪唑酸盐），[（NO）2 Fe（OPh）（- SC 4 H 3 S）] -（4），[（NO）2 Fe（p -OPhF）2 ] -（5）和[（NO）2 Fe（SPh）（ONO）] -（6）。配体（[SPh] -，[ - SC 4 H 3 S] -，[C 3 H 3 N 2 ] -，[OPh] -和[NO 2 ] -）对Fe（NO）的结合亲和力2 } 9基序如下配体-位移系列[SPh上] -〜[-SC 4 ħ3 S] - > [C 3 H 3 N 2 ] - > [OPh] - > [NO 2 ] -。研究结果表明，对于阴离子Fe（NO）2 } 9
• Mononuclear Ni(III) Complexes [Ni^III(L)(P(C₆H₃-3-SiMe₃-2-S)₃)]^0/1- (L = Thiolate, Selenolate, CH₂CN, Cl, PPh₃):  Relevance to the Nickel Site of [NiFe] Hydrogenases
  作者：Chien-Ming Lee、Ya-Lan Chuang、Chao-Yi Chiang、Gene-Hsiang Lee、Wen-Feng Liaw

  DOI：10.1021/ic061399g

  日期：2006.12.1

  to yield complex 3 (kobs = (6.01 +/- 0.03) x 10-4 s-1 for conversion of complex 4 into 3 vs kobs = (4.78 +/- 0.02) x 10-5 s-1 for conversion of complex 2 into 3). Interestingly, addition of CH3CN into complex 3 in the presence of sodium hydride yielded the stable Ni(III)-cyanomethanide complex 7 with a NiIII-CH2CN bond distance of 2.037(3) A. The NiIII-SEt bond length of 2.273(1) A in complex 4 is at

  稳定的单核Ni（III）-硫醇盐配合物[NiIII（L）（P（C6H3-3-SiMe3-2-S）3）]-（L = SePh（2），Cl（3），SEt（4），分离2-S-C4H3S（5），CH2CN（7）），并通过UV-vis，EPR，IR，SQUID，CV，1H NMR和单晶X射线衍射进行表征。由单齿配体L和苯硫醇酯环的取代基调节的配合物[NiIII（L）（P（C6H3-3-SiMe3-2-S）3）]-镍中心的碱度（电子密度）提高，促进了稳定性和反应性。与络合物3在-1.17 V（vs Cp2Fe / Cp2Fe +）不可逆还原相比，络合物[NiIII（SePh）（P（o-C6H4S）3）]-，2、4和7的循环伏安图显示可逆NiIII / II氧化还原过程分别具有E（1/2）= -1.20，-1.26，-1.32和-1.34 V（相对于Cp2Fe / Cp2Fe +）。与含有苯硒酸酯配位的
• The synthesis of four isomeric bisthienothiepinones
  作者：Jeffrey A. Charonnat、Joseph M. Muchowski、Peter H. Nelson

  DOI：10.1002/jhet.5570200447

  日期：1983.7

  The displacement reaction between sodium thiophene-3-thiolate and methyl 3-(bromomethyl)thiophene-2-carboxylate (5) gave the expected thioether 7a. Basic hydrolysis afforded the carboxylic acid 7b; conversion to the acid chloride, and treatment of the latter with stannic chloride then produced the bisthienothiepinone 1. Using analogous reactions the isomers 2-4 were also synthesized.

  噻吩-3-硫代硫酸钠与3-（溴甲基）噻吩-2-羧酸甲酯（5）之间的置换反应得到了预期的硫醚7a。碱性水解，得到羧酸7b。转化为酰氯，然后用氯化锡处理后者，生成了bisthienothiepinone 1。使用类似的反应，还合成了异构体2-4。
• Cyclizations and Rearrangements of Samarium Diiodide-Generated Vinyl Radicals
  作者：Laura Capella、Pier Carlo Montevecchi、Maria Luisa Navacchia

  DOI：10.1021/jo00128a013

  日期：1995.11

  Vinyl bromides 1, 5, 15, 20, 23, 27, 33a,b, 41a-c, 44a-c, 46a,b, 52a,b, 55a, 56a,b, and 60a,b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals. Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(pi-exo)exo, 6-(pi-endo)exo, and 6-(pi-exo)exo mode, respectively. Radical 7 undergoes competitive 1,5-hydrogen translocation. Vinyl radicals 21 and 24 readily cyclize on the proximal double bond, leading to 5- and 6-membered rings, respectively. Thienyl-substituted radical 28 leads to a product deriving from 5-exo cyclization on the thiophene ring and subsequent beta-fission of the C-S bond, whereas thienyl-substituted radicals 34a,b undergo almost exclusively 1,5-hydrogen translocation. Aryl-substituted radicals obtained from vinyl bromides 41, 44, 46, 52, and 55 do not form any products deriving from 5-exo or 6-exo cyclization (or ipso cyclization). Finally, naphthyl-substituted radicals 57a and 61a give only direct reduction products, whereas the radical 61b affords, in addition to the direct reduction product, a rearranged product deriving from a 1,3-radical migration of the naphthylthio group. Evidence is reported for the reduction of EWG-substituted benzene rings and thio-substituted naphthalene rings to radical anions, which can fragment on the side chain with the elimination of allyl radicals. alpha-Oxy(and alpha-thio)-substituted radicals deriving from 1,5-shift rearrange to alcohols (and thiols) through a Wittig rearrangement or a cyclization/fragmentation process.
• Synthesis of new 3-thiosubstituted carbacephem antibiotics and their activity against penicillin resistant Streptococcus pneumoniae
  作者：Larry C. Blaszczak、Clark N. Eid、Jane Flokowitsch、G.Stuart Gregory、Stephen A. Hitchcock、George W. Huffman、Daniel R. Mayhugh、Michael J. Nesler、David A. Preston、Mohammad Zia-Ebrahimi

  DOI：10.1016/s0960-894x(97)00412-5

  日期：1997.9

  The synthesis of a series of 3-thiosubstituted carbacephem derivatives is described. The compounds were assayed against penicillin susceptible, intermediate and resistant strains of Streptococcus pneumoniae. Several analogs displayed potent in vitro activity against these organisms. (C) 1997 Elsevier Science Ltd.