3-甲基-2-氮杂啶酮 | 58521-61-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 3-甲基-2-氮杂啶酮
• 英文名称: 3-methyl-2-azetidinone
• 英文别名: 3-methylazetidin-2-one；3-methylazetidione；3-methyl-azetidin-2-one
• CAS: 58521-61-2
• 化学式: C₄H₇NO
• mdl: MFCD19217124
• 分子量: 85.1057
• InChiKey: XYAPRMQTKAOTJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-甲基-2-氮杂啶酮 、 3-溴丙炔 在 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以93%的产率得到N-(2-丙炔基)-3-甲基-2-氮杂环丁酮
  参考文献：
  名称：

  .beta.-Lactam analogs of oxotremorine. 3- and 4-Methyl-substituted 2-azetidinones

  摘要：

  Four beta-lactam analogues (8-11) of oxotremorine were synthesized and assayed for muscarinic and antimuscarinic activity on the isolated guinea pig ileum. The pharmacological results were compared with those obtained previously with the beta-lactam analogue 7 and the 3-, 4-, and 5-methyl-substituted 2-pyrrolidones 2-6. The new compounds were less potent than the corresponding 2-pyrrolidones, regardless of whether they showed agonist (10 and 11), partial agonist (8), or antagonist properties (9) in the ileum assay. The agonists 10 and 11 were about 200-fold less potent than 7. Compounds 8-11 also were less potent than the similarly substituted 2-pyrrolidones in inhibiting the binding of the muscarinic antagonist (-)-[3H]-N-methylscopolamine in homogenates of the rat cerebral cortex.

  DOI：

  10.1021/jm00164a018
• 作为产物：
  描述：

  3-氨基异丁酸 在 sulfenamide ⁽⁵⁾ 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以89%的产率得到3-甲基-2-氮杂啶酮
  参考文献：
  名称：

  使用亚磺酰胺/三苯膦从β-氨基酸制备β-内酰胺的简便方法

  摘要：

  通过用N-烷基-2-苯并噻唑基亚磺酰胺和三苯基膦处理，β-，γ-和δ-氨基酸易于高产率地环化为相应的β-，γ-和δ-内酰胺。

  DOI：

  10.1016/0040-4039(95)00658-y

文献信息

• Reduction process for the preparation of 4-unsubstituted azetidin-2-ones
  申请人：——

  公开号：US04683303A1

  公开（公告）日：1987-07-28

  Novel process for the preparation of azetidin-2-ones of the formula ##STR1## wherein R.sup.1 and R.sup.2 independently from each other are hydrogen, or an organic group linked to the ring carbon via a carbon atom, a nitrogen atom or an oxygen atom, characterized in that a corresponding 4-acyloxyazetidin-2-one, which is substituted by a group --O--CO--R.sup.3 at the 4-position, wherein R.sup.3 is hydrogen or an organic radical stable at the reaction conditions, is reacted with a complex metal hydride comprising reactive hydride ions, such as, lithium borohydride, sodium borohydride, potassium borohydride, zinc borohydride or tetraorganoammonium borohydride.

  制备azetidin-2-酮的新方法，其化学式为##STR1##其中R.sup.1和R.sup.2独立地是氢，或通过碳原子、氮原子或氧原子与环碳相连的有机基团，其特征在于，将相应的4-酰氧基azetidin-2-酮与在4位被一个--O--CO--R.sup.3基团取代的基团反应，其中R.sup.3是在反应条件下稳定的氢或有机基团，所用的试剂是包含反应性氢化物离子的复杂金属氢化物，如硼氢化锂、硼氢化钠、硼氢化钾、硼氢化锌或四有机铵硼氢化物。
• Enantiopure<i>N</i>-Benzyloxycarbonyl-β²-amino Acid Allyl Esters from Racemic β-Lactams by Dynamic Kinetic Resolution using<i>Candida antarctica</i>Lipase B
  作者：Eleonora Gianolio、Resmi Mohan、Albrecht Berkessel

  DOI：10.1002/adsc.201500820

  日期：2016.1.7

  The dynamic kinetic resolution of α‐substituted racemic β‐lactams by alcoholytic ring‐opening, catalyzed by immobilized lipase B from Candida antarctica is described. With this process, a variety of racemic α‐substituted N‐Cbz‐azetidinones (Cbz=benzyloxycarbonyl) was transformed to the corresponding N‐Cbz‐protected β2‐amino acid allyl esters with high enantioselectivity (up to 99%) and high yields

  描述了由固定化的南极假丝酵母脂肪酶B催化的醇取代的开环反应，动态地分解了α-取代的外消旋β-内酰胺。与此过程中，各种外消旋α取代的Ñ -Cbz -氮杂环丁酮基（Cbz =苄）转化成相应的Ñ -Cbz保护的β 2个高对映选择性（高达99％）和高收率氨基酸烯丙基酯（最高定量）在室温下。
• Nitrosative deamination of 1-aminoazetidin-2-ones. An entry to N-unsubstituted β-lactams
  作者：James D. White、Steven T. Perri、Steven G. Toske

  DOI：10.1016/s0040-4039(00)93960-1

  日期：1992.1

  Nitrosative deamination of 1-aminoazetidin-2-ones was carried out with diphenylnitrosamine to give the N-unsubstituted systems, thus completing a route to β-lactams by photochemical ring contraction of pyrazolidin-3 ones.

  用二苯基亚硝胺对1-氨基氮杂环丁烷-2-酮进行亚硝化脱氨基反应，得到N-未取代的体系，从而通过吡唑烷啶-3的光化学环收缩完成了通往β-内酰胺的途径。
• Highly efficient oxazolone-derived reagents for beta-lactam formation from beta-amino acids
  作者：Takehisa Kunieda、Tomohisa Nagamatsu、Tsunehiko Higuchi、Masaaki Hirobe

  DOI：10.1016/s0040-4039(00)86712-x

  日期：——
• A C–N insertion of β-lactam to benzyne: unusual formation of acridone
  作者：Jimin Kim、Brian M. Stoltz

  DOI：10.1016/j.tetlet.2012.07.026

  日期：2012.9

  Intermolecular insertion of benzyne into the C-N bond of a beta-lactam is described. This sigma-insertion is followed by ring expansion that produces dihydroquinolinone, which rapidly reacts with an additional benzyne unit to afford an acridone through intramolecular C-C bond formation to the carbonyl group and rapid elimination of ethylene. (C) 2012 Elsevier Ltd. All rights reserved.