(4S)-4-methylazetidin-2-one | 26757-74-4

• 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: (4S)-4-methylazetidin-2-one
• 英文别名: (S)-4-methylazetidin-2-one；(S)-4-methyl-1H-2-azetidinone；(S)-4-Methylazetidinon-2
• CAS: 26757-74-4
• 化学式: C₄H₇NO
• 分子量: 85.1057
• InChiKey: XMSFNEZQRPOHAR-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 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：

  正丁基锂 、 (4S)-4-methylazetidin-2-one 在 triethyloxonium fluoroborate 作用下， 生成 (4S)-2,2-dibutyl-4-methylazetidine
  参考文献：
  名称：

  Conformational and Chiroptical Properties of N-Nitrosoazetidines

  摘要：

  Optically active N-nitrosoazetidines, containing the isolated nitrosoazetidine chromophore, i.e. (2R)-1-nitroso-2-methylazetidine (2) and (4S)-1-nitroso-2,2-dibutyl-4-methylazetidine (5), are synthesized, and their H-1 NMR, CD, and UV spectra are studied. A topomerization mechanism, structural features, and chiroptical properties of the individual isomers of the parent 1-nitrosoazetidine (1) and its (2R)-2-methyl, (4R)-2,2,4-trimethyl, and (4S)-2,2-diethyl-4-methyl derivatives 2-4 are studied theoretically by means of non-empirical quantum chemical calculations. It is shown that the CD spectra of N-nitrosoazetidines can be interpreted on the basis of the two-position Z,E-equilibrium, taking into account the nonplanarity of the nitrosoazetidine chromophore. The Cotton effect sign of the n-pi* transition at 380 nm is determined by the intrinsic chirality of the chromophore and obeys a spiral rule.

  DOI：

  10.1021/ja00108a010
• 作为产物：
  描述：

  L-β-高丙氨酸盐酸盐 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以86%的产率得到(4S)-4-methylazetidin-2-one
  参考文献：
  名称：

  The Directed Cleavage of Substituted 1-Phenylethylamines: A Novel Route to Enantiomerically Pure β-Amino Acid Esters and β-Lactams

  摘要：

  一种从光学活性 1- 获得对映体纯 ß-氨基酸酯和 ß-内酰胺（例如 (3S,4S)-1-(叔丁基二甲基甲硅烷基-4-甲基-2-氧氮杂环丁烷-3-甲酸甲酯)的有效新途径描述了通过 Birch 还原和随后的臭氧分解进行区域特异性裂解。

  DOI：

  10.1055/s-1991-26583

文献信息

• β-Lactams in synthesis: short syntheses of cobactin analogs
  作者：Andrew J. Walz、Marvin J. Miller

  DOI：10.1016/j.tetlet.2007.05.085

  日期：2007.7

  Mycobactins facilitate assimilation of iron by mycobacteria. Synthetic analogs with structural variation of the cobactin component have potent anti-TB activity. A new method for the synthesis of cobactin analogs is presented. The key process involves single-step coupling reactions between an amine of a cyclic (l)-lysine derived hydroxamic acid with cyanide activated β-lactams.

  分支杆菌素促进分枝杆菌对铁的吸收。具有烟草素成分结构变化的合成类似物具有有效的抗结核病活性。提出了一种新的合成cobactin类似物的方法。关键过程涉及环状（l）-赖氨酸衍生的异羟肟酸的胺与氰化物活化的β-内酰胺之间的单步偶联反应。
• Asymmetric synthesis with chiral hydroxylamines.
  作者：S.W. Baldwin、J. Aubé

  DOI：10.1016/s0040-4039(00)95680-6

  日期：1987.1
• BALDWIN S. W.; AUBE J., TETRAHEDRON LETT., 28,(1987) N 2, 179-182
  作者：BALDWIN S. W.、 AUBE J.

  DOI：——

  日期：——
• The Directed Cleavage of Substituted 1-Phenylethylamines: A Novel Route to Enantiomerically Pure β-Amino Acid Esters and β-Lactams
  作者：Gerhard Bringmann、Torsten Geuder

  DOI：10.1055/s-1991-26583

  日期：——

  An efficient novel access to enantiomerically pure ß-amino acid esters and ß-lactams (e.g., methyl (3S,4S)-1-(tert-butyldimethylsilyl-4-methyl-2-oxoazetidine-3-carboxylate) from optically active 1-arylethylamines is described. Regiospecific cleavage is performed by Birch reduction and subsequent ozonolysis.

  一种从光学活性 1- 获得对映体纯 ß-氨基酸酯和 ß-内酰胺（例如 (3S,4S)-1-(叔丁基二甲基甲硅烷基-4-甲基-2-氧氮杂环丁烷-3-甲酸甲酯)的有效新途径描述了通过 Birch 还原和随后的臭氧分解进行区域特异性裂解。
• Conformational and Chiroptical Properties of N-Nitrosoazetidines
  作者：G. V. Shustov、A. Rauk

  DOI：10.1021/ja00108a010

  日期：1995.1

  Optically active N-nitrosoazetidines, containing the isolated nitrosoazetidine chromophore, i.e. (2R)-1-nitroso-2-methylazetidine (2) and (4S)-1-nitroso-2,2-dibutyl-4-methylazetidine (5), are synthesized, and their H-1 NMR, CD, and UV spectra are studied. A topomerization mechanism, structural features, and chiroptical properties of the individual isomers of the parent 1-nitrosoazetidine (1) and its (2R)-2-methyl, (4R)-2,2,4-trimethyl, and (4S)-2,2-diethyl-4-methyl derivatives 2-4 are studied theoretically by means of non-empirical quantum chemical calculations. It is shown that the CD spectra of N-nitrosoazetidines can be interpreted on the basis of the two-position Z,E-equilibrium, taking into account the nonplanarity of the nitrosoazetidine chromophore. The Cotton effect sign of the n-pi* transition at 380 nm is determined by the intrinsic chirality of the chromophore and obeys a spiral rule.