(chlorocarbonyl)disulfanyl chloride | 79341-73-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 英文名称: (chlorocarbonyl)disulfanyl chloride
• 英文别名: Chlordisulfanylameisensaeurechlorid；S-chlorosulfanyl chloromethanethioate
• CAS: 79341-73-4
• 化学式: CCl₂OS₂
• 分子量: 163.048
• InChiKey: SRSBPZFAVQTXQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (chlorocarbonyl)disulfanyl chloride 以53%的产率得到
  参考文献：
  名称：

  MOLTZEN E. K.; JENSEN B.; SENNING A., ACTA CHEM. SCAND., 40,(1986) N 8, 609-618

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(chlorocarbonyl)trisulfane 反应 8.0h， 以49%的产率得到(chlorocarbonyl)disulfanyl chloride
  参考文献：
  名称：

  Novel symmetrical and mixed carbamoyl and aminopolysulfanes by reactions of (alkoxydichloromethyl)polysulfanyl substrates with N-methylaniline

  摘要：

  DOI：

  10.1021/jo00360a039

文献信息

• Garlic-inspired trisulfide linkers for thiol-stimulated H₂S release
  作者：Francesca Ercole、Michael R. Whittaker、Michelle L. Halls、Ben J. Boyd、Thomas P. Davis、John F. Quinn

  DOI：10.1039/c7cc03820h

  日期：——

  Garlic-derived polysulfides (e.g., diallyl trisulfide, DATS) act as potent donors of the cell-signalling mediator H2S when exposed to endogenous thiols. Inspired by this chemistry, we incorporated a trisulfide linkage into a conjugate comprising an mPEG tail and a cholesteryl head via thiol-mediated fragmentation chemistry. The synthesized conjugate releases H2S upon exposure to thiol even at intracellular

  大蒜衍生的多硫化物（例如，二烯丙基三硫化物，DATS）在暴露于内源性硫醇时，是细胞信号传导介质H 2 S的有效供体。受此化学方法的启发，我们通过硫醇介导的裂解化学方法将三硫键结合到包含mPEG尾部和胆固醇基头部的缀合物中。将合成的缀合物释放ħ 2小号在暴露于硫醇，即使在胞内水平。
• H₂S-Donating trisulfide linkers confer unexpected biological behaviour to poly(ethylene glycol)–cholesteryl conjugates
  作者：Francesca Ercole、Yuhuan Li、Michael R. Whittaker、Thomas P. Davis、John F. Quinn

  DOI：10.1039/c9tb02614b

  日期：——

  by the properties of the naturally occurring H2S donor, diallyl trisulfide (DATS, extracted from garlic), the biological behaviour of trisulfide-bearing PEG-conjugates was explored. Specifically, three conjugates comprising an mPEG tail and a cholesteryl head were investigated: conjugates bridged by a trisulfide linker (T), a disulfide linker (D) or a carbamate linker (C), and a fourth comprising two

  受到天然存在的H2S供体，二烯丙基三硫化物（DATS，从大蒜中提取）的特性的启发，研究了带有三硫化物的PEG-缀合物的生物学行为。具体而言，研究了三种包含mPEG尾部和胆固醇基头部的缀合物：由三硫键（T），二硫键（D）或氨基甲酸酯键（C）桥接的缀合物，以及第四条包含两个由三硫键桥接的mPEG尾巴的缀合物。链接器（P）。使用HEK293细胞中的荧光化学探针和安培传感器监测悬浮细胞中的释放进行H2S测试，证明了三硫键结合物T和P在存在细胞硫醇的情况下释放H2S的能力。对HEK293细胞的细胞毒性和细胞保护能力表明T是研究的缀合物中耐受性最好的，而且，值得注意的是，T的施加对细胞具有保护作用，有效地消除了与共同给药的C相关的毒性。缀合物及其组合与HEK细胞膜的相互作用还研究了细胞，以及ROS的产生。发现C引起明显的膜扰动，这与细胞活力的高损失和ROS的明显产生有关，特别是在线粒体中。然而，T并没
• Synthesis and Pharmacology of Novel Analogues of Oxytocin and Deaminooxytocin:  Directed Methods for the Construction of Disulfide and Trisulfide Bridges in Peptides^,^,
  作者：Lin Chen、Ivana Zoulíková、Jiřina Slaninová、George Barany

  DOI：10.1021/jm9607156

  日期：1997.3.1

  Using as models the neurohypophyseal nonapeptide hormone oxytocin and its analogue deaminooxytocin, several directed routes to formation of sulfur-sulfur bridges have been developed and evaluated. The linear sequences (through common octapeptide-resin intermediates) were assembled smoothly on tris(alkoxy)benzylamide (PAL) poly(ethylene glycol)-polystyrene (PEG-PS) graft supports, using stepwise Fmoc

  使用神经下垂体九肽激素催产素及其类似物脱氨基催产素作为模型，已开发并评估了形成硫-硫桥的几种直接途径。使用逐步Fmoc固相化学方法，将线性序列（通过常见的八肽树脂中间体）平稳地组装在三（烷氧基）苄基酰胺（PAL）聚（乙二醇）-聚苯乙烯（PEG-PS）接枝载体上。S-2,4,6-三甲氧基苄基（Tmob），S-乙酰氨基甲基（Acm）和/或一系列硫代硫代碳酸酯提供了β-巯基丙酸（Mpa）和/或半胱氨酸（Cys）的侧链保护和氨基甲酰基亚磺酰基保护/活化基团：S-（甲氧基羰基）亚磺酰基（Scm），S-（甲氧基羰基）二硫烷基（Sscm），S-（N-甲基-N-苯基氨基甲酰基）亚磺酰基（Snm）和S-（N-甲基-N-苯基氨基甲酰基）二硫基（Ssnm）。S-Snm（优选）或S-Scm的硫解取代提供了分子内环化的肽二硫化物，化学结构与S-Ssnm（再次优选）和S-Sscm的同系物提供了相应的三硫化物以及少量的
• Scaled-up Synthesis and Characterization of Oxytocin Trisulfide
  作者：Robert P. Hammer、Melissa A. Butrie、Karen Davidson、Phillip T. Goldblatt、Alex M. Schrader、Joseph J. Dalluge、Allyn Becker、George Barany

  DOI：10.1007/s10989-023-10580-9

  日期：——

  trisulfide (3), was required on a multi-100 mg scale, as part of an analytical method validation process for the clinically and commercially important product “Oxytocin Injection,” which is a sterile isotonic injectable formulation of oxytocin (2). We report here that previous chemistry from our academic laboratory can be successfully scaled up in the biotechnology sector to indeed provide pure 3 (overall

  标题肽三硫化物催产素 ( 3 ) 需要 100 毫克以上的规模，作为临床和商业重要产品“催产素注射液”分析方法验证过程的一部分，该产品是催产素的无菌等渗注射制剂（2）。我们在此报告，我们学术实验室之前的化学反应可以在生物技术领域成功扩大规模，从而确实提供纯3（总产率 6 – 7%，> 95% 纯度）。放大的合成还产生了适度水平的催产素四硫化物 ( 4 )，甚至更高的同系物，这有些出乎意料。描述和讨论了合成、纯化和表征（通过 HPLC、质谱和氨基酸分析）的方案，以及对我们的发现的可能机制解释。
• Experimental and theoretical studies on bis(chlorocarbonyl)trisulfane, ClC(O)SSSC(O)Cl
  作者：Yeny A. Tobón、Melina V. Cozzarín、Carlos O. Della Védova、Rosana M. Romano

  DOI：10.1016/j.molstruc.2009.04.025

  日期：2009.7

  Bis(chlorocarbonyl)trisulfane, ClC(O)SSSC(O)Cl, was prepared by the reaction of (CH3)(2)CHOC(S)SC-(S)OCH(CH3)(2) and SO2Cl2 at 65 degrees C. The compound was characterized and identified by vibrational spectroscopy, GC-MS, matrix isolation and photochemical studies as well as by quantum chemical calculations. Matrix photochemical studies and vibrational spectra were interpreted in terms of the presence of three forms with syn-gauche-gauche-syn (I), syn-(-)gauche-gauche-syn (II), and syn-gauche-gauche-anti (III) conformations. The syn and anti conformations correspond to the orientation of each C=O group with respect to the adjacent S-S bond, while the gauche form refers to the conformation around each of the S-S bond. This result is in agreement with quantum chemical calculations which predict structures II and III to be higher in energy than conformer I by about 1.51/0.98 and 2.52/2.84 kcal/mol for the B3LYP/MP2 approximations in combination with the 6-31+G* basis set. An assignment of the liquid IR and Raman spectra is proposed for ClC(O)SSSC(O)Cl, as well as the possible mechanisms of the photolysis in Ar and N-2 matrices. The presence of ClC(O)SSCl as a photochemical product opens the possibility of further investigations for this family. (C) 2009 Elsevier B.V. All rights reserved.