4-(邻甲苯基)氮杂环丁烷-2-酮 | 83725-15-9

• 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: 4-(邻甲苯基)氮杂环丁烷-2-酮
• 英文名称: 4-(o-tolyl)azetidin-2-one
• 英文别名: 4-(2-Methylphenyl)-2-azetidinone；4-(2-methylphenyl)azetidin-2-one
• CAS: 83725-15-9
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: AOXGPABNMZJZPT-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  366.5±31.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  4-(邻甲苯基)氮杂环丁烷-2-酮 在 水 作用下， 以 甲基叔丁基醚 为溶剂， 反应 105.0h， 生成 N-acetyl 2'-methyl-β-phenylalanine methyl ester
  参考文献：
  名称：

  Enzymatic preparation of (S)-3-amino-3-(o-tolyl)propanoic acid, a key intermediate for the construction of Cathepsin inhibitors

  摘要：

  Enantiomerically pure (S)-3-amino-3-(o-tolyl)propanoic acid [(S)-6], identified as the preferred enantiomeric form for the construction of novel beta-amino acid derivatives as inhibitors of Cathepsin, was prepared through both indirect and direct enzymatic strategies. Resolution of hydroxymethylated beta-lactam (+/-)-1 through Burkholderia cepacia lipase PSIM-catalysed R-selective butyrylation (E > 200) was first carried out in t-BuOMe. Treatment of the unreacted (S)-1 with 18% HCl then furnished the desired (S)-6 center dot HCl. Next, Candida antarctica lipase B catalysed the ring cleavage of racemic 4-(o-tolyl)azetidin-2-one [(+/-)-2] with excellent R enantioselectivity (E > 200), either in t-BuOMe with added H2O as nucleophile or in H2O at 60 degrees C. Hydrolysis of the less reactive beta-lactam enantiomer [(S)-2] with 18% HCl afforded (S)-6 center dot HCl. A direct enzymatic route to enantiomeric (S)-6 was finally optimized through the lipase PSIM-catalysed S-enantioselective (E>200) hydrolysis of racemic ethyl 3-amino-3-(o-tolyl)propanoate [(+/-)-3] in t-BuOMe with added H2O at 45 degrees C or in H2O at 3 degrees C. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.04.001
• 作为产物：
  描述：

  2-甲基苯甲醛 在 正丁基锂 、 碳酸氢钠 作用下， 反应 16.0h， 生成 4-(邻甲苯基)氮杂环丁烷-2-酮
  参考文献：
  名称：

  Chlorosulphonyl Isocyanate Addition too-Dialkylaminostyrenes: Preparation of 6-(o-Dialkylaminophenyl)-uracils

  摘要：

  DOI：

  10.1055/s-1982-29893

文献信息

• Easy access to constrained peptidomimetics and 2,2-disubstituted azetidines by the unexpected reactivity profile of α-lithiated N-Boc-azetidines
  作者：Giovanna Parisi、Emanuela Capitanelli、Antonella Pierro、Giuseppe Romanazzi、Guy J. Clarkson、Leonardo Degennaro、Renzo Luisi

  DOI：10.1039/c5cc06323j

  日期：——

  The unprecedented reactivity profile of lithiatedN-Boc-2-arylazetidines gave access either to new azetidine-based peptidomimetics or to the regioselective functionalization of the azetidine ring.

  锂化N-Boc-2-芳基氮杂环丙烷的前所未有的反应特性使得要么可以获得基于新的氮杂环丙烷的肽类类似物，要么可以实现氮杂环丙烷环的区域选择性官能化。
• Photocatalytic Carboxylation of C−N Bonds in Cyclic Amines with CO ₂ by Consecutive Visible‐Light‐Induced Electron Transfer
  作者：Lin Chen、Quan Qu、Chuan‐Kun Ran、Wei Wang、Wei Zhang、Yi He、Li‐Li Liao、Jian‐Heng Ye、Da‐Gang Yu

  DOI：10.1002/anie.202217918

  日期：2023.3.6

  A photocatalytic carboxylation of C−N bonds in cyclic amines with CO2 is realized by consecutive photo-induced electron transfer (ConPET). This mild and transition-metal-free protocol provides a general and practical route to valuable β-, γ-, δ- and ϵ-amino acids.

  通过连续光诱导电子转移 (ConPET) 实现环胺中 C-N 键与 CO 2的光催化羧化。这种温和且不含过渡金属的方案为有价值的 β-、γ-、δ- 和 ε- 氨基酸提供了一条通用且实用的途径。
• HOLLYWOOD, F.;SUSCHITZKY, H.;HULL, R., SYNTHESIS, BRD, 1982, N 8, 662-665
  作者：HOLLYWOOD, F.、SUSCHITZKY, H.、HULL, R.

  DOI：——

  日期：——
• Chlorosulphonyl Isocyanate Addition to<i>o</i>-Dialkylaminostyrenes: Preparation of 6-(<i>o</i>-Dialkylaminophenyl)-uracils
  作者：Frank Hollywood、Hans Suschitzky、Roy Hull

  DOI：10.1055/s-1982-29893

  日期：——
• Enzymatic preparation of (S)-3-amino-3-(o-tolyl)propanoic acid, a key intermediate for the construction of Cathepsin inhibitors
  作者：Enikő Forró、Gábor Tasnádi、Ferenc Fülöp

  DOI：10.1016/j.molcatb.2013.04.001

  日期：2013.9

  Enantiomerically pure (S)-3-amino-3-(o-tolyl)propanoic acid [(S)-6], identified as the preferred enantiomeric form for the construction of novel beta-amino acid derivatives as inhibitors of Cathepsin, was prepared through both indirect and direct enzymatic strategies. Resolution of hydroxymethylated beta-lactam (+/-)-1 through Burkholderia cepacia lipase PSIM-catalysed R-selective butyrylation (E > 200) was first carried out in t-BuOMe. Treatment of the unreacted (S)-1 with 18% HCl then furnished the desired (S)-6 center dot HCl. Next, Candida antarctica lipase B catalysed the ring cleavage of racemic 4-(o-tolyl)azetidin-2-one [(+/-)-2] with excellent R enantioselectivity (E > 200), either in t-BuOMe with added H2O as nucleophile or in H2O at 60 degrees C. Hydrolysis of the less reactive beta-lactam enantiomer [(S)-2] with 18% HCl afforded (S)-6 center dot HCl. A direct enzymatic route to enantiomeric (S)-6 was finally optimized through the lipase PSIM-catalysed S-enantioselective (E>200) hydrolysis of racemic ethyl 3-amino-3-(o-tolyl)propanoate [(+/-)-3] in t-BuOMe with added H2O at 45 degrees C or in H2O at 3 degrees C. (C) 2013 Elsevier B.V. All rights reserved.