甘氨酸,N-乙酰基-N-(4-甲氧苯基)-,1,1-二甲基乙基酯 | 122846-17-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甘氨酸,N-乙酰基-N-(4-甲氧苯基)-,1,1-二甲基乙基酯
• 英文名称: N-<(tert-butoxycarbonyl)methyl>-N-(4-methoxyphenyl)acetamide
• 英文别名: tert-butyl 2-(N-acetyl-4-methoxyanilino)acetate
• CAS: 122846-17-7
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: ADWVOEBTUPUJFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甘氨酸,N-乙酰基-N-(4-甲氧苯基)-,1,1-二甲基乙基酯 在 sodium hydroxide 、 N-碘代丁二酰亚胺 、 正丁基锂 作用下， 反应 2.0h， 生成 3,4-cis-4-(tert-butoxycarbonyl)-1-(4-methoxyphenyl)-3-(1-methylethenyl)-2-azetidinone
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by oxidative coupling of dianions of acyclic tertiary amides

  摘要：

  Tertiary amides RCH2CON(R')CH2Z, where Z is an electron-withdrawing group, were converted into dianions by treatment with 2 equiv of n-butyllithium or tert-butyllithium, and the dianions were oxidized with N-iodosuccinimide (NIS) or a Cu(II) carboxylate to form beta-lactams stereoselectively. The stereochemistry of beta-lactam formation depends on the oxidant; NIS is cis-selective, whereas Cu(II) is nonselective or slightly trans-selective. A high degree of asymmetric induction in the formation of beta-lactams was achieved by using (R)-1-phenylethylamine as a chiral auxiliary. This asymmetric ring closure was applied to the preparation of cis-beta-lactam 31, an intermediate for the synthesis of the monobactam antibiotic carumonam.

  DOI：

  10.1021/jo00032a047
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 4'-甲氧基乙酰苯胺 在 苄基三乙基溴化铵 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 甘氨酸,N-乙酰基-N-(4-甲氧苯基)-,1,1-二甲基乙基酯
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by oxidative coupling of dianions of acyclic tertiary amides

  摘要：

  Tertiary amides RCH2CON(R')CH2Z, where Z is an electron-withdrawing group, were converted into dianions by treatment with 2 equiv of n-butyllithium or tert-butyllithium, and the dianions were oxidized with N-iodosuccinimide (NIS) or a Cu(II) carboxylate to form beta-lactams stereoselectively. The stereochemistry of beta-lactam formation depends on the oxidant; NIS is cis-selective, whereas Cu(II) is nonselective or slightly trans-selective. A high degree of asymmetric induction in the formation of beta-lactams was achieved by using (R)-1-phenylethylamine as a chiral auxiliary. This asymmetric ring closure was applied to the preparation of cis-beta-lactam 31, an intermediate for the synthesis of the monobactam antibiotic carumonam.

  DOI：

  10.1021/jo00032a047

文献信息

• A new synthesis of .beta.-lactams through stereoselective oxidative coupling of the dianions of acyclic amides
  作者：Takeo Kawabata、Kenzo Sumi、Tamejiro Hiyama

  DOI：10.1021/ja00199a055

  日期：1989.8

  La synthese du noyau β-lactame se fait via la copulation oxydante d'enolate d'amide utilisant le N-iodo succinimide en tant qu'oxydant

  La 合成 du noyau β-内酰胺本身 fait via la copulation oxydante d'enolate d'amide utilisant le N-iodo succinimide en tant qu'oxydant
• KAWABATA, TAKEO;SUMI, KENZO;HIYAMA, TAMEJIRO, J. AMER. CHEM. SOC., 111,(1989) N7, C. 6843-6845
  作者：KAWABATA, TAKEO、SUMI, KENZO、HIYAMA, TAMEJIRO

  DOI：——

  日期：——
• Stereoselective synthesis of .beta.-lactams by oxidative coupling of dianions of acyclic tertiary amides
  作者：Takeo Kawabata、Tatsuya Minami、Tamejiro Hiyama

  DOI：10.1021/jo00032a047

  日期：1992.3

  Tertiary amides RCH2CON(R')CH2Z, where Z is an electron-withdrawing group, were converted into dianions by treatment with 2 equiv of n-butyllithium or tert-butyllithium, and the dianions were oxidized with N-iodosuccinimide (NIS) or a Cu(II) carboxylate to form beta-lactams stereoselectively. The stereochemistry of beta-lactam formation depends on the oxidant; NIS is cis-selective, whereas Cu(II) is nonselective or slightly trans-selective. A high degree of asymmetric induction in the formation of beta-lactams was achieved by using (R)-1-phenylethylamine as a chiral auxiliary. This asymmetric ring closure was applied to the preparation of cis-beta-lactam 31, an intermediate for the synthesis of the monobactam antibiotic carumonam.