α-((4-Chlorophenyl)thio)propanoyl chloride | 76161-45-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: α-((4-Chlorophenyl)thio)propanoyl chloride
• 英文别名: 2-(4-Chlorophenyl)sulfanylpropanoyl chloride
• CAS: 76161-45-0
• 化学式: C₉H₈Cl₂OS
• 分子量: 235.134
• InChiKey: XQEITUNMNYXHGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  α-((4-Chlorophenyl)thio)propanoyl chloride 、 羽扇豆宁 以 二氯甲烷 为溶剂， 生成 [(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methyl 2-(4-chlorophenyl)sulfanylpropanoate
  参考文献：
  名称：

  2-(4-R-Phenoxy/phenylthio)alkanoic esters of l-lupinine

  摘要：

  Considering the great pharmacological interest in phenoxy/phenylthioalkanoic esters of open-chain or cyclic aminoalcohols, a set of ten such esters of lupinine was prepared. Initially, their ability to displace [H-3]QNB from rat brain preparation was investigated. With the exception of two, all the prepared esters exhibited good affinity to muscarinic receptors (on a non-selective basis), with pK(i) in the range 6.67-7.68. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01036-9
• 作为产物：
  描述：

  2-(4-氯-苯基磺胺)丙酸 生成 α-((4-Chlorophenyl)thio)propanoyl chloride
  参考文献：
  名称：

  一些α-芳硫基和α-芳基磺酰基取代的N-甲氧基-N-甲基丙酰胺的1H和13C NMR谱的完全归属

  摘要：

  报告了一些 α-芳硫基和 α-芳基磺酰基取代的 N-甲氧基-N-甲基丙酰胺的 1H 和 13C NMR 谱的完整归属，这些丙酰胺在苯环上带有甲氧基、甲基、氯和硝基作为取代基。版权所有 © 2006 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.1918

文献信息

• Presynaptic Cholinergic Modulators as Potent Cognition Enhancers and Analgesic Drugs. 2. 2-Phenoxy-, 2-(Phenylthio)-, and 2-(Phenylamino)alkanoic Acid Esters
  作者：Fulvio Gualtieri、Claudia Bottalico、Anna Calandrella、Silvia Dei、Maria Paola Giovannoni、Stefania Mealli、Maria Novella Romanelli、Serena Scapecchi、Elisabetta Teodori

  DOI：10.1021/jm00037a023

  日期：1994.5

  leads ((R)-(+)-hyoscyamine and (p-chlorophenyl)propionic acid alpha-tropanyl ester), which show analgesic and nootropic activities as a consequence of increased central presynaptic ACh release, are reported. 2-Phenoxy- and 2-(phenylthio)alkanoic acid esters showed the best results. Several members of these classes possess analgesic properties which are comparable to that of morphine and at the same time

  据报道，对铅的进一步修饰（（R）-（+）-水苏胺和（对-氯苯基）丙酸α-托帕尼酯），由于增加的中央突触前ACh释放而显示出止痛和促智活性。2-苯氧基-和2-（苯硫基）链烷酸酯显示了最佳结果。这些类别中的几个成员具有与吗啡相当的镇痛作用，同时能够逆转由二环胺引起的健忘症。证实作用机制是由于中央毒蕈碱突触中ACh释放的增加所致，控制ACh释放的自体和异体受体极有可能参与其中。根据（R）-（+）-硫辛胺获得的结果，镇痛活性与立体化学有关，因为R-（+）-对映异构体总是比相应的S-（-）-one更有效。根据其效力和急性毒性，选择化合物（+/-）-28（SM21）和（+/-）-42（SM32）进行进一步研究。
• Preparation of 3-alkyl .beta.-lactams via the ketene imine cycloaddition reaction using .alpha.-(phenylthio)alkanoyl halides as starting materials: application to the synthesis of (.+-.)-carbapenem building blocks and related compounds
  作者：Claudio Palomo、Fernando P. Cossio、Jose M. Odiozola、Mikel Oiarbide、Jesus M. Ontoria

  DOI：10.1021/jo00014a017

  日期：1991.7

  Preparation of appropriately substituted 3-alkyl beta-lactams via the ketene (or equivalent)-imine cycloaddition reaction is described. The dehydrochlorination reaction of alpha-(phenylthio)alkanoyl chlorides with triethylamine in the presence of imines derived from cinnamaldehydes and p-anisidine produced a high-yield formation of alpha-phenylthio beta-lactams, which upon desulfuration furnished a variety of 3-alkyl beta-lactams in a highly stereoselective fashion. In contrast, reaction between alpha-haloalkanoyl chlorides and cinnamylideneamines in the presence of triethylamine furnished the corresponding [4 + 2] cycloadducts as main products. Preparation of highly functionalized alpha-alkylidene beta-lactams through thermal decomposition of the corresponding beta-lactam sulfoxides or by cycloaddition of alpha,beta-unsaturated acid chlorides to imino esters in the presence of triethylamine is also described. Addition of Flemming's silylcuprate reagent to alpha-alkylidene beta-lactams furnished the corresponding 3-(1'-(dimethylphenylsilyl(ethyl) beta-lactams as (+/-)-thienamycin intermediates.
• PALOMO, CLAUDIO;COSSIO, FERNANDO P.;ODIZOLA, JOSE M.;OIARBIDE, MIKEL;ONTO+, J. ORG. CHEM., 56,(1991) N4, C. 4418-4428
  作者：PALOMO, CLAUDIO、COSSIO, FERNANDO P.、ODIZOLA, JOSE M.、OIARBIDE, MIKEL、ONTO+

  DOI：——

  日期：——