己烷-1-磺酰氯 | 56506-12-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 中文名称: 己烷-1-磺酰氯
• 英文名称: hexane-1-sulphenyl chloride
• 英文别名: hexanesulfenyl chloride；1-hexanesulfenyl chloride；Hexyl thiohypochlorite
• CAS: 56506-12-8
• 化学式: C₆H₁₃ClS
• 分子量: 152.688
• InChiKey: PKLOCXCFMPIHTB-UHFFFAOYSA-N

物化性质

• 沸点：
  186.9±9.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  己烷-1-磺酰氯 在 重水 、 溶剂黄146 作用下， 以 二氯甲烷 、 氘代甲醇 为溶剂， 生成 S-hexyl hexane-1-sulfinothioate
  参考文献：
  名称：

  New Class of Biodegradable Polymers Formed from Reactions of an Inorganic Functional Group

  摘要：

  Although numerous small molecules have been synthesized with sulfenamide bonds (R2N-SR), this is the first report of the synthesis of polysulfenamides. These polymers are readily synthesized at room temperature using secondary diamines and dithiosuccinimides. The dithiosuccinimides were readily synthesized in one step by the reaction of dithiols such as HS(CH2)(6)SH with N-chlorosuccinimide. The resulting dithiosuccinimides were either recrystallized or readily purified by chromatography on silica gel and required no special handling. The conversions of polymerization ranged from 95 to 98%, and the molecular weights of the polymer reached as high as 6300 g mol(-1). The sulfenamide bond was very stable in organic solvents, and no degradation was observed under atmospheric conditions in C6D6 for 30 days. In contrast, the sulfenamide bond readily decomposed in less than 12 h in D2O. Polysulfenamides were fabricated into micrometer-sized particles loaded with dye and endocytosed into JAWSII immature dendritic and HEK293 cells. Polysulfenamides represent a new class of polymers that are readily synthesized, stable in aprotic solvents, and readily degrade in water.

  DOI：

  10.1021/ma300190b
• 作为产物：
  描述：

  1-己硫醇 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 己烷-1-磺酰氯
  参考文献：
  名称：

  Pharmacological evaluation of disulfiram analogs as antimicrobial agents and their application as inhibitors of fosB-mediated fosfomycin resistance

  摘要：

  酒精戒断药物二硫仑（Antabuse®）的二硫化物类似物被评估其抗微生物活性。对耐甲氧西林金黄色葡萄球菌（MRSA）和其他致病生物的最低抑菌浓度（MIC）数据进行的结构活性关系分析显示，取代基的亲脂性和体积之间存在相关性。具有最佳抗MRSA活性的类似物含有S-辛基二硫化物和N,N-二甲基或N-吡咯烷二硫代氨基甲酸酯取代基。额外测试表明，二硫仑及其S-辛基衍生物均能使金黄色葡萄球菌对磷霉素的杀菌效果产生敏感性。机制研究表明，这些化合物通过硫醇-二硫键交换反应降低了胞内辅因子巴克利硫醇的水平。因此，金黄色葡萄球菌对磷霉素的增敏被归因于可用于fosB失活的细胞内巴克利硫醇池的耗竭。

  DOI：

  10.1038/s41429-022-00500-2

文献信息

• Pharmacological evaluation of disulfiram analogs as antimicrobial agents and their application as inhibitors of fosB-mediated fosfomycin resistance
  作者：Alexandria D. Lewis、Taylor M. Riedel、Meredith B. A. Kesler、Melinda E. Varney、Timothy E. Long

  DOI：10.1038/s41429-022-00500-2

  日期：2022.3

  Disulfide analogs of the alcohol sobriety medication disulfiram (Antabuse®) were evaluated for antimicrobial activity. Structure-activity relationship analyses of MIC data obtained for methicillin-resistant Staphylococcus aureus (MRSA) and other pathogenic organisms revealed correlations between the lipophilicity and bulkiness of the substituents. Analogs conferring optimal anti-MRSA activity contained S-octyl disulfides and either N,N-dimethyl- or N-pyrrolidine dithiocarbamate substituents. Additional testing revealed that both disulfiram and its S-octyl derivative are capable of sensitizing S. aureus to the bactericidal effects of fosfomycin. Mechanistic studies established that the compounds decrease intracellular levels of the fosB cofactor bacillithiol through a thiol-disulfide exchange reaction. The increased fosfomycin susceptibility in S. aureus was thereby attributed to a depleted cellular bacillithiol pool available for inactivation by fosB.

  酒精戒断药物二硫仑（Antabuse®）的二硫化物类似物被评估其抗微生物活性。对耐甲氧西林金黄色葡萄球菌（MRSA）和其他致病生物的最低抑菌浓度（MIC）数据进行的结构活性关系分析显示，取代基的亲脂性和体积之间存在相关性。具有最佳抗MRSA活性的类似物含有S-辛基二硫化物和N,N-二甲基或N-吡咯烷二硫代氨基甲酸酯取代基。额外测试表明，二硫仑及其S-辛基衍生物均能使金黄色葡萄球菌对磷霉素的杀菌效果产生敏感性。机制研究表明，这些化合物通过硫醇-二硫键交换反应降低了胞内辅因子巴克利硫醇的水平。因此，金黄色葡萄球菌对磷霉素的增敏被归因于可用于fosB失活的细胞内巴克利硫醇池的耗竭。
• Biodegradable Polymers with Sulfenamide Bonds for Drug Delivery Applications
  申请人：Bowden Ned B.

  公开号：US20140099506A1

  公开（公告）日：2014-04-10

  The present invention provides polysulfenamides and methods of making same.

  本发明提供了聚硫胺酰胺及其制备方法。
• Metal-free and site-selective α-C–H functionalization of tetrahydrofuran enabled by the photocatalytic generation of bromine radicals
  作者：Can-Ming Zhu、Rong-Bin Liang、Yonghong Xiao、Wei Zhou、Qing-Xiao Tong、Jian-Ji Zhong

  DOI：10.1039/d2gc03347j

  日期：——

  A simple and inherent green photocatalytic approach using commercially available and cheap ⁿBu₄NBr with 4-CzIPN was reported to effectively initiate the site-selective α-C(sp³)-H activation of tetrahydrofuran for C-S and C-C cross-couplings.

  一种简单且固有的绿色光催化方法，利用商业可得且价格便宜的nBu4NBr和4-CzIPN，能够有效地启动四氢呋喃的位点选择性α-C(sp3)-H活化，用于C-S和C-C交叉偶联反应。
• Selective S-Arylation of Sulfenamides with Arynes: Access to Sulfilimines
  作者：Yifeng Guo、Zhe Zhuang、Xiaoying Feng、Quanyu Ma、Ningning Li、Chaochao Jin、Hiroto Yoshida、Jiajing Tan

  DOI：10.1021/acs.orglett.3c02785

  日期：2023.10.6

  Sulfilimines, the aza analogues of sulfoxides, are of increasing interest in medicinal and agrochemical research programs. However, the development of efficient routes for their synthesis has remained relatively unexplored. In this study, we report a transition metal-free, selective S-arylation reaction between sulfenamides and arynes, enabling the facile preparation of structurally diverse sulfilimines

  磺亚胺是亚砜的氮杂类似物，在医药和农业化学研究项目中越来越受到人们的关注。然而，其有效合成路线的开发相对尚未探索。在这项研究中，我们报道了次磺酰胺和芳炔之间的无过渡金属、选择性S-芳基化反应，使得能够在温和和氧化还原中性条件下以良好的收率轻松制备结构多样的硫亚胺。通过放大合成、下游衍生化和稳健性筛选进一步证明了我们方法的应用价值。
• Convenient method for the conversion of thiols and disulfides to the corresponding chlorides
  作者：Ian W. J. Still、Gerald W. Kutney、David McLean

  DOI：10.1021/jo00342a037

  日期：1982.1