α-(Phenylthio)butanoyl chloride | 127055-07-6

• 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-(Phenylthio)butanoyl chloride
• 英文别名: α-phenylthiobutanoyl chloride；2-Phenylsulfanylbutanoyl chloride
• CAS: 127055-07-6
• 化学式: C₁₀H₁₁ClOS
• 分子量: 214.716
• InChiKey: MNNORNRGQSKYER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-(Phenylthio)butanoyl chloride 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (S)-3-Benzenesulfinyl-3-ethyl-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00014a017
• 作为产物：
  描述：

  苯硫酚 在 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 α-(Phenylthio)butanoyl chloride
  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

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。
• De-arylmethylation of N-mono- or N-diarylmethyl-beta-lactams; novel azetizinones having anti-bacterial activity
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0023097A1

  公开（公告）日：1981-01-28

  β-Lactams having a hydrogen atom on the nitrogen atom of the β-lactam ring are prepared by reacting an N-mono-or N-diarylmethyl- β-lactam with an acid or ceric ammonium nitrate to cleave the bond between the nitrogen atom and the mono- or diarylmethyl group; certain 4- substituted-3-phenylthio -2-azetizinones among the starting and product compounds have anti-bacterial activity. A valuable novel intermediate, 4-(2- phenylethenyl)-3-amino-N-di (p-anisyl) -methyl-2- azetizinone of the formula: is prepared by reacting an acid anhydride derivative of a compound of the formula: with a Schiff base of the formula: and treating the resultant crystalline compound with an acid The amino group of the product compound is then acylated to form an amido derivative which is subjected to the above dearylmethylation to form an anti-bacterial substance.

  通过使 N-单甲基或 N-二甲基-β-内酰胺与酸或硝酸铈铵反应，裂解氮原子与单甲基或二甲基二芳基之间的键，制备出在β-内酰胺环的氮原子上有一个氢原子的β-内酰胺；起始化合物和产物化合物中的某些 4-取代-3-苯硫基-2-氮杂环丁酮具有抗菌活性。一种有价值的新型中间体，4-(2-苯基乙烯基)-3-氨基-N-二(对甲氧基)-甲基-2-氮杂环丁酮的化学式如下： 式化合物的酸酐衍生物与式的希夫碱反应制备而成： 的酸酐衍生物与式 然后将产物化合物的氨基酰化形成氨基衍生物，该衍生物经上述去甲基化反应形成抗菌物质。
• Alkyl(phenylthio)ketenes as synthetic equivalents of monoalkylketenes: A concise general route to 3-alkyl β-lactams as carbapenem building-blocks
  作者：Claudio Palomo、Fernando P. Cossío、José M. Odriozola、Mikel Oiarbide、Jesús M. Ontoria

  DOI：10.1016/s0040-4039(01)80749-8

  日期：1989.1
• PALOMO, CLAUDIO;COSSIO, FERNANDO P.;ODRIOZOLA, JOSE M.;OIARBIDE, MIKEL;ON+, TETRAHEDRON LETT., 30,(1989) N4, C. 4577-4580
  作者：PALOMO, CLAUDIO、COSSIO, FERNANDO P.、ODRIOZOLA, JOSE M.、OIARBIDE, MIKEL、ON+

  DOI：——

  日期：——
• 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：——