(4R)-4-methylazetidin-2-one | 26757-75-5

• 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: (4R)-4-methylazetidin-2-one
• CAS: 26757-75-5
• 化学式: C₄H₇NO
• 分子量: 85.1057
• InChiKey: XMSFNEZQRPOHAR-GSVOUGTGSA-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：

  (4R)-4-methylazetidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 (R)-2-甲基吖丁啶
  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：

  (1¹S,4R)-4-methyl-1-(α-methylbenzyl)azetidin-2-one 在 氨 、 sodium 作用下， 反应 2.0h， 以80%的产率得到(4R)-4-methylazetidin-2-one
  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

文献信息

• Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp³)−H Carbamoylation
  作者：David Dailler、Ronan Rocaboy、Olivier Baudoin

  DOI：10.1002/anie.201703109

  日期：2017.6.12

  A general and user‐friendly synthesis of β‐lactams is reported that makes use of Pd0‐catalyzed carbamoylation of C(sp3)−H bonds, and operates under stoichiometric carbon monoxide in a two‐chamber reactor. This reaction is compatible with a range of primary, secondary and activated tertiary C−H bonds, in contrast to previous methods based on C(sp3)−H activation. In addition, the feasibility of an enantioselective

  据报道，β-内酰胺的一般且用户友好的合成方法利用了Pd 0催化的C（sp 3）-H键的氨基甲酰化作用，并在化学计量的一氧化碳下在两腔反应器中运行。与以前的基于C（sp 3）-H活化的方法相反，该反应与一系列伯，仲和活化的叔CH键兼容。另外，证明了使用手性亚膦酸酯配体的对映选择性形式的可行性。最后，该方法可用于合成有价值的对映体纯的无β-内酰胺和β-氨基酸。
• 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
• Stereochemistry of the methylation of the (11S,4S) and (11S,4R) diastereomers of 4-methyl-1-(?-methylbenzyl)azetidin-2-one
  作者：N. N. Romanova、T. G. Tallo、A. A. Borisenko、Yu. G. Bundel'

  DOI：10.1007/bf00509703

  日期：1990.7
• Romanova, N. N.; Tallo, T. G.; Bundel', Yu. G., Russian Journal of Organic Chemistry, 1995, vol. 31, # 3, p. 375 - 377
  作者：Romanova, N. N.、Tallo, T. G.、Bundel', Yu. G.

  DOI：——

  日期：——