trans-4-Methyl-3-aethyl-azetidinon-(2) | 149951-76-8

• 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-Methyl-3-aethyl-azetidinon-(2)
• 英文别名: (3S,4S)-3-ethyl-4-methylazetidin-2-one
• CAS: 149951-76-8
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: ZFCHNBPKRWHYSU-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2S,3S)-3-amino-2-ethylbutanoic acid 在 N,N'-二环己基碳二亚胺 作用下， 生成 trans-4-Methyl-3-aethyl-azetidinon-(2)
  参考文献：
  名称：

  使用Nicholas反应可多功能合成β-氨基酸。一，对碳青霉烯类β-内酰胺的应用

  摘要：

  使用尼古拉斯反应的施莱伯修饰法制备的具有一般结构10的同型手性乙炔酸已通过涉及Curtius重排然后乙炔键的氧化裂解的两个步骤序列转化为11型β-氨基酸衍生物。氨基酸衍生物11是碳青霉烯类β-内酰胺的极好的前体。

  DOI：

  10.1016/s0040-4039(00)77630-1

文献信息

• β-lactams from esters and silylimines: A revaluation. Synthesis of N-unsubstituted 4-alkyl-β-lactams
  作者：Gianfranco Cainelli、Daria Giacomini、Mauro Panunzio、Giorgio Martelli、Giuseppe Spunta

  DOI：10.1016/s0040-4039(00)96733-9

  日期：1987.1

  The first preparation of enolizable silylimines is reported. The “in situ” trapping of these species with lithium enolates of esters gives rise in fairly good yields to N-unsubstituted 4-alkyl-β-lactams.

  报道了可烯丙基化的水飞蓟宾的第一种制备方法。用酯的烯醇锂“原位”捕集这些物质可提高N-未取代的4-烷基-β-内酰胺的收率。
• Formal Total Syntheses of the β-Lactam Antibiotics Thienamycin and PS-5
  作者：Peter A. Jacobi、Shaun Murphree、Frederic Rupprecht、Wanjun Zheng

  DOI：10.1021/jo952092u

  日期：1996.1.1

  Chiral nonracemic acetylenic acids of general structure 11, prepared using the Schreiber modification of the Nicholas reaction, have been converted to beta-amino acid derivatives of type 12 by a two-step sequence involving Curtius rearrangement followed by oxidative cleavage of the acetylenic bond. Amino acid derivatives 12 are excellent precursors for beta-lactams of the carbapenem class, including the important antibiotics thienamycin (1) and PS-5 (4).
• A New Method for the Synthesis of β-Amino Acid Derivatives and β-Lactams. Reaction of <i>N</i>-Alkoxycarbonyl-1-methoxyamines with Esters
  作者：Naoki Kise、Nasuo Ueda

  DOI：10.1021/jo990821q

  日期：1999.10.1

  The reaction of N-alkoxycarbonyl-1-methoxyamines with esters is an alternative to the reaction of imines with esters for the synthesis of beta-amino acid derivatives. In this reaction, N-alkoxycarbony-1-methoxyamines corresponding to unstable imines can also be employed. Although anti adducts were obtained preferentially in the absence of Ti complexes, the diastereoselectivity of this reaction was reversed by the addition of Ti(OPr-i)(4). The obtained adducts were transformed to the corresponding beta-lactams.
• Poly-beta-peptides from functionalized beta-lactam monomers and antibacterial compositions containing same
  申请人：Stahl S. Shannon

  公开号：US20070087404A1

  公开（公告）日：2007-04-19

  Disclosed is a method of making β-polypeptides. The method includes polymerizing β-lactam-containing monomers in the presence of a base initiator and a co-initiator which is not a metal-containing molecule to yield the product β-polypeptides. Specifically disclosed are methods wherein the base initiator is potassium t-butoxide, lithium bis(trimethylsilyl)amide (LiN(TMS) 2 ), potassium bis(trimethyl-silyl)amide, and sodium ethoxide, and the reaction is carried out in a solvent such as chloroform, dichloromethane, dimethylsulfoxide, or tetrahydrofuran.
• POLY-BETA-PEPTIDES FROM FUNCTIONALIZED BETA-LACTAM MONOMERS AND ANTIBACTERIAL COMPOSITIONS CONTAINING SAME
  申请人：Stahl Shannon S.

  公开号：US20100222250A1

  公开（公告）日：2010-09-02

  Disclosed is a method of making β-polypeptides. The method includes polymerizing β-lactam-containing monomers in the presence of a base initiator and a co-initiator which is not a metal-containing molecule to yield the product β-polypeptides. Specifically disclosed are methods wherein the base initiator is potassium t-butoxide, lithium bis(trimethylsilyl)amide (LiN(TMS) 2 ), potassium bis(trimethyl-silyl)amide, and sodium ethoxide, and the reaction is carried out in a solvent such as chloroform, dichloromethane, dimethylsulfoxide, or tetrahydrofuran.