Acetonylmercapto-essigsaeure | 33691-97-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Acetonylmercapto-essigsaeure
• 英文别名: Acetic acid, [(2-oxopropyl)thio]-；2-(2-oxopropylsulfanyl)acetic acid
• CAS: 33691-97-3
• 化学式: C₅H₈O₃S
• mdl: MFCD19159845
• 分子量: 148.183
• InChiKey: QHNOJBXNPFOXSV-UHFFFAOYSA-N

物化性质

• 熔点：
  43-45 °C
• 沸点：
  183-185 °C(Press: 11 Torr)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetonylmercapto-essigsaeure 在 双氧水 作用下， 以 neat (no solvent) 为溶剂， 反应 0.03h， 以99%的产率得到C₅H₈O₄S
  参考文献：
  名称：

  在 MCM-41@Tryptophan-Cd 和 MCM-41@Tryptophan-Hg 作为新型可回收纳米催化剂存在的情况下，硫醇的高效氧化偶联和硫化物的氧化

  摘要：

  摘要 通过将 Cd 或 Hg 配合物固定在 MCM-41 上合成了两种多相催化剂 MCM-41@Tryptophan-Cd 和 MCM-41@Tryptophan-Hg 作为新型、高效、可回收且稳定的纳米催化剂，用于硫化物氧化为亚砜和氧化反应。硫醇偶联成相应的二硫化物。这些功能化配合物通过 FT-IR 光谱、热重分析 (TGA)、粉末 X 射线衍射 (XRD) 和 N2 吸附-解吸等温线进行表征。所设计的催化剂在室温下以短反应时间以高产率成功氧化各种硫化物和硫醇，并在不显着损失其催化活性的情况下回收数次。图形摘要已提出在温和反应条件下合成固定在介孔 MCM-41 表面的 Cd 和 Hg 色氨酸复合物。在对这些催化剂进行表征后，研究了它们用于合成亚砜和二硫化物衍生物的催化活性。

  DOI：

  10.1007/s10562-018-2379-3
• 作为产物：
  描述：

  methyl [(2-oxopropyl)sulfanyl]acetate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以55%的产率得到Acetonylmercapto-essigsaeure
  参考文献：
  名称：

  Rhodamine spirolactam sensors operated by sulfur-cooperated metal complexation

  摘要：

  New rhodamine Schiff base sensors were developed to improve selective sensing by introducing sulfide, ester, and dithiocarbonate groups, as well as using ketones coupled to rhodamine-hydrazine. Metal sensing proceeded through the 1:1 complexation of the metal ion for most sensors in the presence of Cu2+ and Hg2+. A sensor carrying a dithiocarbonate group responded selectively to Hg2+ showing a strong colorimetric change and intense fluorescence. The association constants of the sensors were determined from a linear plot performed at micro-molar concentrations to afford values in the range of 10(4). Sensing was interrupted at the initial time of Hg2+ exposure due to the isomerization of imine and preferential metal bonding of two dithiocarbonate groups regardless of the main structure of rhodamine. The sensors exhibited the reversible and reproducible performance for Hg2+ sensing. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2017.07.019

文献信息

• Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity
  作者：Steven Gunawan、Christopher Hulme

  DOI：10.1039/c3ob40900g

  日期：——

  1,5-Disubstituted tetrazoles are an important drug-like scaffold known for their ability to mimic the cis-amide bond conformation. The scaffold is readily accessible via substitution of the carboxylic acid component of the Ugi multi-component reaction (MCR) with TMSN3 in what is herein denoted the Ugi-azide reaction. This full paper presents a concise, novel, general strategy to access a plethora of new heterocylic scaffolds utilizing tethered aldo/keto-acids/esters in the Ugi-azide reaction followed by a ring closing event that generates novel highly complex bis-heterocyclic lactam-tetrazoles.

  1,5-二取代四唑是一类重要的类药物骨架，以其能够模拟顺式酧胺键构象而闻名。该骨架可以通过将Ugi多组分反应（MCR）中的羧酸成分替换为TMSN3，从而在此文中称为Ugi-叠氮反应的方式轻易获得。本篇论文提出了一种简洁、新颖、通用的策略，利用连接在Ugi-叠氮反应中的醛/酮酸/酯，通过环合反应生成新型高度复杂的二杂环内酰胺-四唑结构，来构建大量的新型杂环骨架。
• An Umpolung Oxa-[2,3] Sigmatropic Rearrangement Employing Arynes for the Synthesis of Functionalized Enol Ethers
  作者：Rahul N. Gaykar、Malini George、Avishek Guin、Subrata Bhattacharjee、Akkattu T. Biju

  DOI：10.1021/acs.orglett.1c00911

  日期：2021.5.7

  An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C═O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic

  据报道涉及芳烃的oxa- [2,3]σ重排以酮为主体，其中的C═O键极性相反。β-酮硫醚和芳烃在原位生成的硫烷基化物经过有效的重排，可以轻松，稳健地合成高官能度的烯醇醚，并具有出色的官能团相容性。初步的机理研究排除了在这种情况下运行Pummerer型重排的可能性。
• New nitrofurans amenable by isocyanide multicomponent chemistry are active against multidrug-resistant and poly-resistant Mycobacterium tuberculosis
  作者：Mikhail Krasavin、Vladislav Parchinsky、Grigory Kantin、Olga Manicheva、Marine Dogonadze、Tatiana Vinogradova、Bianka Karge、Mark Brönstrup

  DOI：10.1016/j.bmc.2017.02.003

  日期：2017.3

  A set of structurally diverse N-amino delta-lactams decorated with a 5-nitro-2-furyl moiety was synthesized using isocyanide-based multicomponent chemistry and evaluated for antibacterial activity. Three compounds displayed a selective and potent (MIC 22-33 mu M) inhibition of M. tuberculosis H(37)Rv strain growth, while other Gram-positive (MRSA and E. faecium) or Gram-negative (E. coli, P. aeruginosa, A. baumannii, K. pneumoniae) pathogens were not affected. The compounds also displayed moderate low cytotoxicity, as demonstrated in cell line viability assays. Several multidrug-and poly-resistant patient-derived M. tuberculosis strains were found to be susceptible to treatment with these compounds. The three most potent compounds share a significant structural similarity which provides a basis for further scaffold-hopping analog design. (C) 2017 Elsevier Ltd. All rights reserved.
• Proline-like β-turn mimics accessed via Ugi reaction involving monoprotected hydrazines
  作者：Mikhail Krasavin、Vladislav Parchinsky、Alexei Shumsky、Igor Konstantinov、Anton Vantskul

  DOI：10.1016/j.tetlet.2009.12.141

  日期：2010.3

  A four-center, three-component Ugi-type reaction of a variety of keto acids, Boc- or Cbz-protected hydrazine, and isocyanides offers a simple and high yielding access to cyclic products containing an N-aminolactam unit. The latter are shown to form consistently an intramolecular hydrogen bond leading to a p-turn-like secondary structure. The possibility of integrating such N-aminolactam units (without disruption of the folded structure) into pseudotripeptide fragments is demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.
• Nannini; Molgora; Biasoli, Arzneimittel-Forschung/Drug Research, 1977, vol. 27, # 2, p. 343 - 352
  作者：Nannini、Molgora、Biasoli

  DOI：——

  日期：——