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：——
• 2-(4-R-Phenoxy/phenylthio)alkanoic esters of l-lupinine
  作者：Anna Sparatore、Fabio Sparatore

  DOI：10.1016/s0014-827x(01)01036-9

  日期：2001.4

  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.
• Complete assignment of1H and13C NMR spectra of some α-arylthio and α-arylsulfonyl substituted N-methoxy-N-methyl propionamides
  作者：Nelson L. C. Domingues、Mirta G. Mondino、Adriana K. C. A. Reis、Roberto Rittner、Filipe S. Lima、Paulo R. Olivato

  DOI：10.1002/mrc.1918

  日期：2007.1

  The complete assignments of the 1H and 13C NMR spectra of the some α‐arylthio and α‐arylsulfonyl substituted N‐methoxy‐N‐methyl propionamides, bearing methoxy, methyl, chloro, and nitro as substituents at the phenyl ring are reported. Copyright © 2006 John Wiley & Sons, Ltd.

  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.