acetyl-chloro-sulfane | 6405-82-9

• 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: acetyl-chloro-sulfane
• 英文别名: 1-oxoethanesulfenyl chloride；acetyl sulfenyl chloride；Acetylsulfenyl Chloride；acetyl sulfenylchloride；acetylsulfur chloride；acetic hypochlorous thioanhydride；1-(Chlorosulfanyl)-1-oxoethane；S-chloro ethanethioate
• CAS: 6405-82-9
• 化学式: C₂H₃ClOS
• 分子量: 110.564
• InChiKey: ANWTVOZZMFLZRI-UHFFFAOYSA-N

物化性质

• 沸点：
  42-43 °C(Press: 18 Torr)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  acetyl-chloro-sulfane 、 三苯甲硫醇 以 乙醚 为溶剂， 反应 24.0h， 以30%的产率得到tritylacetyldisulfide
  参考文献：
  名称：

  Understanding Hydrogen Sulfide Storage: Probing Conditions for Sulfide Release from Hydrodisulfides

  摘要：

  Hydrogen sulfide (H2S) is an important biological signaling agent that exerts action on numerous (patho)physiological processes. Once generated, H2S can be oxidized to generate reductant-labile sulfane sulfur pools, which include hydrodisulfides/persulfides. Despite the importance of hydrodisulfides in H2S storage and signaling, little is known about the physical properties or chemical reactivity of these compounds. We report here the synthesis, isolation, and characterization (NMR, IR, Raman, HRMS, X-ray) of a small-molecule hydrodisulfide and highlight its reactivity with reductants, nucleophiles, electrophiles, acids, and bases. Our experimental results establish that hydrodisulfides release H2S upon reduction and that deprotonation results in disproportionation to the parent thiol and S-0, thus providing a mechanism for transsulfuration in the sulfane sulfur pool.

  DOI：

  10.1021/ja505371z
• 作为产物：
  描述：

  乙酰基硫醚 在 磺酰氯 作用下， 反应 0.5h， 以37%的产率得到acetyl-chloro-sulfane
  参考文献：
  名称：

  氢二硫化甲基和氘代二硫化甲基的便捷制备和光谱表征†

  摘要：

  氢二硫化甲基和氘代二硫化甲基已通过四步合成法制备。这些化合物已在光谱上包括微波光谱进行了表征。

  DOI：

  10.1002/hlca.19850680710
• 作为试剂：
  描述：

  二甲基-乙烯基磷酸酯 在 盐酸 、 acetyl-chloro-sulfane 作用下， 生成 Dimethyl thiiran-2-ylphosphonate
  参考文献：
  名称：

  1,2-Epithioethanephosphonic acid esters

  摘要：

  DOI：

  10.1007/bf00953265

文献信息

• Hydropersulfides: H-Atom Transfer Agents Par Excellence
  作者：Jean-Philippe R. Chauvin、Markus Griesser、Derek A. Pratt

  DOI：10.1021/jacs.7b02571

  日期：2017.5.10

  biotransmitter hydrogen sulfide (H2S) and disulfides (RSSR) and/or sulfenic acids (RSOH). RSSH have been investigated for their ability to store H2S in vivo and as a line of defense against oxidative stress, from which it is clear that RSSH are much more reactive to two-electron oxidants than thiols. Herein we describe the results of our investigations into the H-atom transfer chemistry of RSSH, contrasting

  氢过硫化物（RSSH）是通过气态生物递质硫化氢（H 2 S）与二硫化物（RSSR）和/或亚磺酸（RSOH）的反应内生形成的。已经研究了RSSH在体内储存H 2 S的能力以及作为抗氧化应激的防御线，从中可以清楚地看出，RSSH对二电子氧化剂的反应性比硫醇更高。在此，我们描述了对RSSH的H原子转移化学的研究结果，并将其与众所周知的硫醇的H原子转移化学进行了对比。事实上，RSSH优异H-原子供体，以烷基（ķ〜5×10 8中号-1小号-1），烷氧基（ķ〜1×10 9中号-1小号-1），过氧化氢（ķ〜2×10 6中号-1小号-1），和含硫（ķ > 1×10 10中号-1小号-1）自由基，对硫醇的抑制作用可低至1个数量级，最高可至4个数量级。RSSH对H原子转移的固有高反应性很大程度上是基于热力学因素。较弱的RSS–H键解离焓（〜70 kcal / mol）和相关的高硫基自由基稳定性使上述反应放热15–34
• Synthesis and NMR Spectra of<i>para</i>-Substituted Benzyl Hydrodisulfides and Related Compounds
  作者：Shunichi Kawamura、Toyokazu Horii、Takeshige Nakabayashi、Masayuki Hamada

  DOI：10.1246/bcsj.48.2993

  日期：1975.10

  The titled compounds were synthesized and their NMR spectra were measured. The chemical shifts of benzyl hydrodisulfides were not related to σ or σR, while those of the corresponding thiols were related to σ.

  合成标题化合物并测量它们的NMR谱。苄基氢二硫化物的化学位移与σ或σR无关，而相应硫醇的化学位移与σ有关。
• Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines
  作者：Adam W Franz、Svetlana Stoycheva、Michael Himmelhaus、Thomas J J Müller

  DOI：10.3762/bjoc.6.72

  日期：——

  (Oligo)phenothiazinyl thioacetates, synthesized by a one-pot sequence, are electrochemically oxidizable and highly fluorescent. SAMs can be readily formed from thiols prepared by in situ deprotection of the thioacetates in the presence of a gold-coated silicon wafer. Monolayer formation is confirmed by ellipsometry and the results compared to those obtained by force field and DFT calculations.

  (寡)苯并噻嗪硫代乙酸酯，通过一锅法合成，具有电化学氧化性和高荧光性。可以通过在金覆盖的硅片存在下对硫代乙酸酯进行原位去保护来轻松形成巯基制备的自组装单分子膜。通过椭圆测量确认了单分子层的形成，并将结果与力场和密度泛函理论计算结果进行比较。
• Synthesis of alkyl trithioperesters (alkyl thiocarbonyl disulfides)
  作者：David F. Aycock、George R. Jurch

  DOI：10.1021/jo01318a019

  日期：1979.2
• The synthesis of substituted [[3(S)-(acylamino)-2-oxo-1-azetidinyl]thio]acetic acids
  作者：Steven R. Woulfe、Marvin J. Miller

  DOI：10.1021/jo00366a010

  日期：1986.8