[(E)-2-Methyl-3-phenyl-prop-2-en-(E)-ylideneamino]-acetic acid methyl ester | 112383-75-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: [(E)-2-Methyl-3-phenyl-prop-2-en-(E)-ylideneamino]-acetic acid methyl ester
• 英文别名: methyl 2-[(2-methyl-3-phenylprop-2-enylidene)amino]acetate
• CAS: 112383-75-2
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: RAPJOTRHZXYJKU-UHFFFAOYSA-N

物化性质

• 沸点：
  327.8±42.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [(E)-2-Methyl-3-phenyl-prop-2-en-(E)-ylideneamino]-acetic acid methyl ester 在 二甲基硫 、 臭氧 、 三乙胺 、 N,N-二甲基磷氨基二氯化物 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  N，N-二甲基磷酰胺二氯化物：一种方便的试剂，用于从乙酸和亚胺制备β-内酰胺

  摘要：

  描述了一种用于由乙酸和亚胺制备β-内酰胺的方便试剂。还报道了从3-双（乙硫基）β-内酰胺制备α-酮-β-内酰胺的新途径。还进行了4-乙基-β-内酰胺与重氮甲烷的反应。

  DOI：

  10.1016/s0040-4039(00)96016-7

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