S-2-pyridyl 10-undecenethioate | 134781-63-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-2-pyridyl 10-undecenethioate
• 英文别名: S-pyridin-2-yl 10-undecenethioate；pyridin-2-yl undec-10-enethioate；S-pyridin-2-yl undec-10-enethioate
• CAS: 134781-63-8
• 化学式: C₁₆H₂₃NOS
• 分子量: 277.431
• InChiKey: JHDPOZFBYKGDRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-2-pyridyl 10-undecenethioate 在 氨 、 碳酸氢钠 、 三乙胺 、 间氯过氧苯甲酸 、 zinc(II) chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 211.0h， 生成 3-hydroxy-2-(8,9-dihydroxynonyl)-5-phenylpentanamide
  参考文献：
  名称：

  芳香族羟酰胺减弱多耐药金黄色葡萄球菌毒素表达。

  摘要：

  耐甲氧西林金黄色葡萄球菌（MRSA）会导致严重感染，目前仅有很少的有效抗生素疗法。为了应对这一挑战，迫切需要具有新颖且无阻力作用方式的化学实体。在这里，我们介绍了一种新的羟酰胺化合物，该化合物可有效减少各种金黄色葡萄球菌中毁灭性毒素的表达。和MRSA菌株。通过转录组分析以及基于亲和力的蛋白质谱分析研究了分子机制。几种致病相关基因的下调表明抑制了中央毒力相关途径。基于质谱的化学蛋白质组学揭示了推定的分子靶标。在MRSA小鼠皮肤感染模型中，使用羟酰胺进行的全身治疗显示脓肿大小明显减少。与直接解决细菌存活的抗生素相比，缺乏体外抗药性的研究进一步强调了靶向毒力可能导致治疗选择时间延长的发现。

  DOI：

  10.1002/chem.201503981
• 作为产物：
  描述：

  2-十一烯酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.75h， 生成 S-2-pyridyl 10-undecenethioate
  参考文献：
  名称：

  4, 4' disubstituted 4H-cyclopentadithiophene and new methods for synthesising the same

  摘要：

  公开号：

  EP2397475B1

文献信息

• 4, 4' DISUBSTITUTED 4H-CYCLOPENTADITHIOPHENE AND NEW METHODS FOR SYNTHESISING THE SAME
  申请人：Vanderzande Dirk

  公开号：US20110313175A1

  公开（公告）日：2011-12-22

  The present preferred embodiments relate to a method for the synthesis of a compound having the following general formula: the method comprising the step of reacting, in presence of a diprotic acid having a negative pKa, a compound having the general formula: wherein R 1 and R 2 are organic groups and wherein X and Y are independently selected from the group consisting of hydrogen, chloro, bromo, iodo, boronic acid, boronate esters, borane, pseudohalogen and organotin. It further relates to compounds so obtained and to compounds resulting from the ring closure of compound (II).

  本发明的首选实施例涉及一种合成具有以下一般式的化合物的方法：该方法包括在具有负pKa的二元酸存在下反应具有以下一般式的化合物：其中R1和R2是有机基团，而X和Y独立地选自氢、氯、溴、碘、硼酸、硼酸酯、硼烷、伪卤素和有机锡的群。它还涉及由化合物（II）环合而成的化合物和由此获得的化合物。
• Facile, green, and functional group-tolerant reductions of carboxylic acids…in, or with, water
  作者：Karthik S. Iyer、Chandler Nelson、Bruce H. Lipshutz

  DOI：10.1039/d3gc00517h

  日期：——

  Facile reductions of carboxylic acids to aldehydes or alcohols can be effected under mild conditions upon initial conversion to their corresponding S-2-pyridyl thioesters. Upon treatment with a commercially available and air-stable nickel pre-catalyst and silane as a stoichiometric reductant, aldehydes are formed in moderate to good yields. Alternatively, the 1-pot conversion of acids to their thioester

  羧酸向醛或醇的轻松还原可以在温和条件下在初始转化为其相应的S -2-吡啶基硫酯时实现。在用市售且空气稳定的镍预催化剂和硅烷作为化学计量还原剂处理后，醛以中等到良好的收率形成。或者，可以将酸一锅法转化为其硫酯衍生物，然后在用硼氢化钠处理后还原为醇。使用这些绿色反应介质可以转化从高度功能化的酸到默克信息库中的离析物的各种起始材料。
• Development and characterization of improved β-lactone-based anti-virulence drugs targeting ClpP
  作者：Evelyn Zeiler、Vadim S. Korotkov、Katrin Lorenz-Baath、Thomas Böttcher、Stephan A. Sieber

  DOI：10.1016/j.bmc.2011.07.047

  日期：2012.1

  Here, we report the synthesis and in depth characterization of a second generation B-lactone derived virulence inhibitors. Based on initial results that emphasized the intriguing possibility to disarm bacteria in their virulence the present study develops this concept further and analyses the potential of this strategy for drug development. We were able to expand the collection of bioactive compounds via an efficient synthetic route. Testing of all compounds revealed several hits with anti-virulence activity. Moreover, we demonstrated that these molecules act solely by reducing virulence but not killing bacteria which is an important prerequisite for preserving the useful microbiome. Finally, incubation of lactones with eukaryotic cell lines indicated a tolerable cytotoxicity which is essential for entering animal studies. (C) 2011 Elsevier Ltd. All rights reserved.
• Cyclization of 9-substituted decanoic acid derivatives to 9-decanolide and 9-decanolactam
  作者：Marti Bartra、Jaume Vilarrasa

  DOI：10.1021/jo00017a027

  日期：1991.8

  Several standard and some novel cyclization reactions have been applied to 9-substituted decanoic acids to establish which are the optimum procedrues for lactonization and lactamization at 80-degrees-C under identical high-dilution conditions. The methods of Galli-Mandolini and Kellogg (cyclization of 9-bromodecanoate ion), Gerlach (cyclization of S-2-pyridyl 9-hydroxydecanethioate in the presence of AgClO4), and Yamaguchi (activation of the carboxyl group as a mixed with anhydride) in the presence of an excess of DMAP appear to be the most useful for the preparation of the 10-membered lactone, phoracantolide I, under these conditions. Analogously, treatment of S-2-pyridyl 9-azidodecanethioate with Sn(SePh)3-afforded the best yield of the 10-membered lactam. The mixed anhydrides RCOOCOAr (Ar = 2,4,6-trichlorophenyl) are more reactive than thioesters RCOSPy (Py = 2-pyridyl) with benzyl alcohol or benzylamine; it is confirmed that the addition of DMAP activates the reaction of alcohols with mixed anhydrides much more than with pyridyl thioesters, while the addition of Ag+ strongly activates RCOSPy in relation to either RCOOCOAr or RCOOSO2Mes.
• US8329923B2
  申请人：——

  公开号：US8329923B2

  公开（公告）日：2012-12-11