(1¹S,4R)-4-methyl-1-(α-methylbenzyl)azetidin-2-one | 89578-36-9

• 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: (1¹S,4R)-4-methyl-1-(α-methylbenzyl)azetidin-2-one
• 英文别名: N((S)-α-Phenylethyl)-4(R)-methylazetidin-2-one；(4R)-4-methyl-1-<(S)-1-phenylethyl>-2-azetidinone；(1'S,4R)-1-(1'-phenylethyl)-4-methylazetidin-2-one；(4R)-4-methyl-1-[(1S)-1-phenylethyl]azetidin-2-one
• CAS: 89578-36-9
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: YFUQHGFWJZOZPK-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (R)-3-((S)-1-Phenyl-ethylamino)-butyryl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (1¹S,4R)-4-methyl-1-(α-methylbenzyl)azetidin-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

• Asymmetric radical cyclization leading to β-lactams: Stereoselective synthesis of chiral key intermediates for carbapenem antibiotics PS-5 and thienamycin
  作者：Hiroyuki Ishibashi、Chisato Kameoka、Kazuya Kodama、Masazumi Ikeda

  DOI：10.1016/0040-4020(95)00902-7

  日期：1996.1

  A stereoselective synthesis of β-lactams by 4-exo-trig radical cyclizations of N-[2,2-bis(phenylthio)ethenyl]-α-bromo amides bearing a chiral inductor on the nitrogen atom has been examined. Bromide 8, upon treatment with Bu3SnH in the presence of AIBN in boiling benzene, gave a mixture of (4S)-2-azetidinone 12a and its (4R)-isomer 12b in a ratio of 71:29 and 69% combined yield. Similar treatment of

  已经研究了通过在氮原子上带有手性感应剂的N- [2,2-双（苯硫基）乙烯基]-α-溴酰胺的4- exo-trig自由基环化的立体选择性合成β-内酰胺的方法。溴化物8在AIBN存在下于沸腾的苯中用Bu 3 SnH处理时，得到比例为71:29和69％的（4 S）-2-氮杂环丁酮12a和（4 R）-异构体12b的混合物综合产量。用Bu 3 SnH对α-溴丁酰胺11进行类似处理，得到反式-（4 S）-2-氮杂环丁酮17a及其主要化合物（4 R）-异构体17b（70：30，77％的总收率）。在（+）-PS-5的合成中，化合物17a被转化为24，一种手性关键中间体（25）。在侧链上带有一个额外的立体生成中心[（S）-氧官能度]的溴化物28的环化以更高的（4S）-立体选择性进行，从而得到氮杂环丁酮29a作为主要产物及其（4R）-异构体29b以78:22的比例和40％的总收率。化合物29a通过氧官能度的转
• Diastereoface-differentiating synthesis of substituted .beta.-lactams from chiral imines and/or chiral .alpha.-chloro iminium chlorides
  作者：Ewa Rogalska、Czeslaw Belzecki

  DOI：10.1021/jo00182a015

  日期：1984.4
• 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：——
• POMAHOBA, N. N.;TALLO, T. G.;BORISENKO, A. A.;BUNDEL, YU. G., XIMIYA GETEROTSIKL. SOED.,(1990) N, S. 914-920
  作者：POMAHOBA, N. N.、TALLO, T. G.、BORISENKO, A. A.、BUNDEL, YU. G.

  DOI：——

  日期：——