trans-4-p-Anisyl-1-<(4'-methoxybenzylidene)amino>-3-methyl-3-methoxy-2-azetidinone

• 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: trans-4-p-Anisyl-1-<(4'-methoxybenzylidene)amino>-3-methyl-3-methoxy-2-azetidinone
• 英文别名: (3S,4S)-3-methoxy-4-(4-methoxyphenyl)-1-[(E)-(4-methoxyphenyl)methylideneamino]-3-methylazetidin-2-one
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: XQHUQGDMPYLUSO-XNWDXEOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-4-p-Anisyl-1-<(4'-methoxybenzylidene)amino>-3-methyl-3-methoxy-2-azetidinone 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 (Z)-1-(p-Methoxyphenyl)-2-methoxy-prop-1-en 、 (E)-1-(p-Anisyl)-2-methoxypropene
  参考文献：
  名称：

  Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone

  摘要：

  Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity. Di- and trisubstituted olefin derivatives are available through this procedure. Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization. The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring. This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.

  DOI：

  10.1021/jo00124a008
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 氧气 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 34.0h， 生成 trans-4-p-Anisyl-1-<(4'-methoxybenzylidene)amino>-3-methyl-3-methoxy-2-azetidinone
  参考文献：
  名称：

  2,3-Diaza-1,3-dienes (Azines) as Substrates for the Staudinger Reaction. Synthesis and Reactivity of N-Imino-.beta.-lactams

  摘要：

  The reaction of aromatic and aliphatic azines with different ketene precursors, such as the acid chloride/Et(3)N system, alkoxychromium(0) carbenes, and free diphenyl ketene, gives N-imino-beta-lactams in good to excellent yields, with good levels of cis,trans-selectivity. A wide variety of symmetrically-substituted azines derived from aldehydes and ketones are compatible with the Staudinger reaction. Chiral N-imino-beta-lactams derived from symmetrically or unsymmetrically (mixed) chiral azines are also obtained in good yields as essentially single enantiomers (de > 95%). Different reaction intermediates, including hemiaminals, oxadiazols, and hydrazides have been isolated. Free diphenyl ketene forms Diels-Alder adducts and N-acylazadienes in addition to the previously reported N-imino-beta-lactams, The usual reactivity of the beta-lactam ring is modified in N-imino-beta-lactams by the presence of the imino group. Thus, beta-hydrazonoesters, N-alkylamino-beta-lactams, and NH-beta-lactams can be efficiently obtained by base-catalyzed 2-azetidinone ring opening, catalytic hydrogenation, and ozonolysis, respectively.

  DOI：

  10.1021/jo00105a014

文献信息

• 2,3-Diaza-1,3-dienes (Azines) as Substrates for the Staudinger Reaction. Synthesis and Reactivity of N-Imino-.beta.-lactams
  作者：Benito Alcaide、Miguel Miranda、Javier Perez-Castells、Concepcion Polanco、Miguel A. Sierra

  DOI：10.1021/jo00105a014

  日期：1994.12

  The reaction of aromatic and aliphatic azines with different ketene precursors, such as the acid chloride/Et(3)N system, alkoxychromium(0) carbenes, and free diphenyl ketene, gives N-imino-beta-lactams in good to excellent yields, with good levels of cis,trans-selectivity. A wide variety of symmetrically-substituted azines derived from aldehydes and ketones are compatible with the Staudinger reaction. Chiral N-imino-beta-lactams derived from symmetrically or unsymmetrically (mixed) chiral azines are also obtained in good yields as essentially single enantiomers (de > 95%). Different reaction intermediates, including hemiaminals, oxadiazols, and hydrazides have been isolated. Free diphenyl ketene forms Diels-Alder adducts and N-acylazadienes in addition to the previously reported N-imino-beta-lactams, The usual reactivity of the beta-lactam ring is modified in N-imino-beta-lactams by the presence of the imino group. Thus, beta-hydrazonoesters, N-alkylamino-beta-lactams, and NH-beta-lactams can be efficiently obtained by base-catalyzed 2-azetidinone ring opening, catalytic hydrogenation, and ozonolysis, respectively.
• Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone
  作者：Benito Alcaide、Javier Perez-Castells、Concepcion Polanco、Miguel A. Sierra

  DOI：10.1021/jo00124a008

  日期：1995.9

  Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity. Di- and trisubstituted olefin derivatives are available through this procedure. Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization. The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring. This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.