α-(Phenylthio)isovaleryl chloride | 127055-08-7

• 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)isovaleryl chloride
• 英文别名: 3-Methyl-2-phenylsulfanylbutanoyl chloride
• CAS: 127055-08-7
• 化学式: C₁₁H₁₃ClOS
• 分子量: 228.743
• InChiKey: HAYKHZTVQOMOLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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)isovaleryl chloride 以 乙醚 为溶剂， 生成 1-acetoxy-4-methyl-3-phenylthio-2-pentanone
  参考文献：
  名称：

  Pusino,A. et al., Gazzetta Chimica Italiana, 1978, vol. 108, p. 557 - 565

  摘要：

  DOI：

文献信息

• 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.
• 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：——
• Pusino,A. et al., Gazzetta Chimica Italiana, 1978, vol. 108, p. 557 - 565
  作者：Pusino,A. et al.

  DOI：——

  日期：——