pentaerythrityl tetrathioacetate | 230950-27-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: pentaerythrityl tetrathioacetate
• 英文别名: S-[3-acetylsulfanyl-2,2-bis(acetylsulfanylmethyl)propyl] ethanethioate
• CAS: 230950-27-3
• 化学式: C₁₃H₂₀O₄S₄
• 分子量: 368.563
• InChiKey: IVFUNAHEFXOWOD-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C(Solv: methanol (67-56-1))
• 沸点：
  470.9±45.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  pentaerythrityl tetrathioacetate 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 38.5h， 生成
  参考文献：
  名称：

  Conformational Analysis of Spiro-bis-dithiepins:  A Peculiar Case of Axial Chirality

  摘要：

  Spiro-bis-dithiepins are synthesized via dehydrative ring expansion in alpha-hydroxyalkyl spiro-bis-dithianes. Atypical of spiranes possessing axial chirality, the two most stable conformers of substituted spiro-bis-dithiepin have virtually colinear double bonds; i.e., each enantiomer exists in a form of two energy degenerate syn and anti conformations. Because of the high polarizability of the vinyl sulfide moiety, spiro-bis-dithiepins bearing electron-withdrawing substituents offer access to two-state systems possessing large dipole moments, which can be modulated by conformational events.

  DOI：

  10.1021/ol062172s
• 作为产物：
  描述：

  乙醇-2-氯碳酸酯(2:1) 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以87%的产率得到pentaerythrityl tetrathioacetate
  参考文献：
  名称：

  基于二噻烷的光不稳定分子系统的合成

  摘要：

  Synthesis 2001, No. 8, 18 06 2001. 文章标识符：1437-210X,E;2001,0,08,1133,1142,ftx,en;C00801SS.pdf。© Georg Thieme Verlag Stuttgart · 纽约 ISSN 0039-7881 摘要：描述了基于二硫代锂加成羰基化合物的光不稳定分子系统的合成。螺结构的二噻烷，例如 2,4,8,10-四噻螺[5.5]十一烷和 2,4-二噻-8,10-二氧杂螺[5.5]十一烷被用作系链，因此允许采用模块化方法来构建一组不同的光裂解分子。发现从简单取代的苯甲醛到甲酰化苯并冠醚、碳水化合物或杯芳烃的各种羰基化合物都适用于这种化学。

  DOI：

  10.1055/s-2001-15057

文献信息

• Rigid Orthogonal Bis-TEMPO Biradicals with Improved Solubility for Dynamic Nuclear Polarization
  作者：Eric L. Dane、Björn Corzilius、Egon Rizzato、Pierre Stocker、Thorsten Maly、Albert A. Smith、Robert G. Griffin、Olivier Ouari、Paul Tordo、Timothy M. Swager

  DOI：10.1021/jo202349j

  日期：2012.2.17

  The synthesis and characterization of oxidized bis-thioketal-trispiro dinitroxide biradicals that orient the nitroxides in a rigid, approximately orthogonal geometry are reported. The biradicals show better performance as polarizing agents in dynamic nuclear polarization (DNP) NMR experiments as compared to biradicals lacking the constrained geometry. In addition, the biradicals display improved solubility

  报道了氧化双硫缩酮三螺二硝基氧双自由基的合成和表征，这些双自由基将氮氧化物定向在刚性的、近似正交的几何形状中。与缺乏几何约束的双自由基相比，双自由基在动态核极化 (DNP) NMR 实验中显示出更好的极化剂性能。此外，由于极性亚砜的存在，双自由基在水性介质中的溶解度有所提高。结果表明，双自由基中硫原子的氧化态不会显着影响自由基的取向，我们得出结论，含有氧化态混合物的双自由基极化剂可用于提高溶解度而不会降低性能.
• Efficient and accelerated growth of multifunctional dendrimers using orthogonal thiol–ene and SN2 reactions
  作者：Naresh Kottari、Yoann M. Chabre、Tze Chieh Shiao、Rabindra Rej、René Roy

  DOI：10.1039/c3cc46633g

  日期：——

  An orthogonal coupling strategy was developed by combining thiol–ene and SN2 reactions, which was subsequently applied to the accelerated synthesis of multifunctional dendrimers using carbohydrate building blocks. In surface plasmon resonance (SPR) studies, the β-D-galactopyranoside-coated dendrimer exhibited nM binding affinity with the bacterial LecA lectin extracted from Pseudomonas aeruginosa.

  通过结合巯基烯和 SN2 反应，开发了一种正交偶联策略，随后将其应用于利用碳水化合物构建模块加速合成多功能树枝状聚合物。在表面等离子体共振（SPR）研究中，δ-D-吡喃半乳糖苷包裹的树枝状聚合物与从铜绿假单胞菌中提取的细菌 LecA 凝集素表现出 nM 的结合亲和力。
• Synthesis and stereochemistry of some new spiro and polyspiro-1,3-dithiane derivatives
  作者：Şerban Andrei Gâz、Eric Condamine、Niculina Bogdan、Anamaria Terec、Elena Bogdan、Yvan Ramondenc、Ion Grosu

  DOI：10.1016/j.tet.2008.05.065

  日期：2008.7

  The synthesis of new spiro and trispiro compounds with 2,4,8,10-tetrathiaspiro[5.5]undecane and 7,11,18,21-tetrathia[5.2.2.5.2.2]heneicosane units is reported. The structural analysis was carried out by NMR investigations and the X-ray single crystal molecular structure determined for one of the compounds. The barriers for the flipping of the 1,3-dithiane units are determined by variable temperature

  报道了具有2,4,8,10-四硫杂螺[5.5]十一烷和7,11,18,21-四硫杂[5.2.2.5.2.2]十八烯烷单元的新螺和三螺化合物的合成。通过NMR研究进行结构分析，并确定其中一种化合物的X射线单晶分子结构。通过可变温度NMR实验确定1，3-二噻吩单元翻转的势垒。
• Expeditive Synthesis of Glycodendrimer Scaffolds Based on Versatile TRIS and Mannoside Derivatives
  作者：Yoann M. Chabre、Christiane Contino-Pépin、Virginie Placide、Tze Chieh Shiao、René Roy

  DOI：10.1021/jo8008935

  日期：2008.7.1

  A new family of glycodendrimer scaffolds containing 12 and 18 peripheral alpha-D-mannopyranosidic units has been synthesized by Cu(I)-catalyzed [1,3]-dipolar cycloadditions using sulfurated dendritic scaffolds bearing alkyne functionalities and novel TRIS derivatives.
• Molecular Assembly and Disassembly:  Novel Photolabile Molecular Hosts
  作者：Yongqin Wan、Oleg Mitkin、Loren Barnhurst、Alexei Kurchan、Andrei Kutateladze

  DOI：10.1021/ol006692d

  日期：2000.11.1

  [GRAPHICS]A new approach to the assembly and photochemical disassembly of molecular hosts is developed. It is based on photoinduced fragmentation in hydroxyalkyl dithianes and utilizes a novel spiro-bis-dithiane as a photolabile molecular tether to link two formylated macromolecular blocks, e.g., formyl calixarenes or formyl dibenzocrown ethers. A key feature of this molecular system is that after an assembly-disassembly cycle the starting macromolecular blocks are recovered intact and can be used again.