cis-3-Ethyl-4-(hydroxymethyl)-1-(4-methoxyphenyl)azetidin-2-one | 128474-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: cis-3-Ethyl-4-(hydroxymethyl)-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: cis-1-p-anisyl-3-ethyl-4-(hydroxymethyl)azetidin-2-one；(3S,4S)-3-ethyl-4-(hydroxymethyl)-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 128474-72-6
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: BBCCICIQIXKJAJ-NWDGAFQWSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  472.5±20.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-3-Ethyl-4-(hydroxymethyl)-1-(4-methoxyphenyl)azetidin-2-one 在 溴化二甲基溴化锍 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 cis-1-(p-methoxyphenyl)-3-ethyl-4-formyl-2-azetidinone
  参考文献：
  名称：

  酰氯-亚氨基酯缩合：直接接触PS-5和PS-6中间体及相关化合物的方法

  摘要：

  在α-亚氨基酯存在下，用三乙胺对烷酰氯进行脱氯化氢反应，可制得3-烷基-4-烷氧基羰基β-内酰胺，产率高，立体选择性高。

  DOI：

  10.1039/c39900000248
• 作为产物：
  描述：

  cis-1-(p-methoxyphenyl)-3-ethyl-4-formyl-2-azetidinone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以95%的产率得到cis-3-Ethyl-4-(hydroxymethyl)-1-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  Stereoselective preparation of mono- and bis-.beta.-lactams by the 1,4-diaza-1,3-diene - acid chloride condensation: scope and synthetic applications

  摘要：

  The dehydrochlorination of a variety of acid chlorides with triethylamine in the presence of 1,4-diaza 1,3-dienes gives in fair to excellent yields, with total stereoselectivity, cis-4-imino beta-lactams 2, cis-4-formyl beta-lactams 3, or C4,C4'-bis-beta-lactams 4, depending on the reaction conditions. The reaction tolerates a wide variety of substituents, including alkoxy, thiophenoxy, amino, aryl, alkyl, alkylidene, and halogen groups, at the ketene moiety. The synthetic versatility of compounds 3 has been demonstrated by their conversion to intermediates in the synthesis of carbapenems PS-5 and PS-6. Base-induced isomerization of compounds 4 to novel bis-gamma-lactams 5, which in turn are aza analogs of glycaric acids, occurred with total retention of the configuration. This process is formally the elongation of glyoxal in four carbons bearing four contiguous stereocenters with total stereoselectivity in only three or four synthetic steps.

  DOI：

  10.1021/jo00048a027

文献信息

• Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry
  作者：Zsuzsanna Sánta、József Nagy、József Nyitrai

  DOI：10.1016/j.tetasy.2006.11.034

  日期：2006.11

  All four traps-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized. (alpha R,6R,7R)- and (alpha S,6S,7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from L- and D-threonine, the configuration at the a-position was inverted by using Mitsunobu reactions providing the (alpha S,6R,7R)- and (alpha R,6S,7S)-diastereomers of the compounds above. A synthetic route to the cis-annelated analogues was also worked out. (c) 2006 Elsevier Ltd. All rights reserved.
• Oxidation of alcohols using bis(trichloromethyl) carbonate as activator of dimethyl sulfoxide
  作者：Claudio Palomo、Fernando P. Cossio、Jesus M. Ontoria、Jose M. Odriozola

  DOI：10.1021/jo00020a046

  日期：1991.9