α-deuterated tert-butyl diazoacetate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-deuterated tert-butyl diazoacetate
• 英文别名: Tert-butyl 2-deuterio-2-diazoacetate；tert-butyl 2-deuterio-2-diazoacetate
• 化学式: C₆H₁₀N₂O₂
• 分子量: 143.15
• InChiKey: JBVSBLLOZVDAAZ-QYKNYGDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-deuterated tert-butyl diazoacetate 在 三乙基硅烷 、 二叔丁基过氧化物 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  与维生素B 12依赖的α-亚甲基戊二酸变位酶作用机理有关的模型实验

  摘要：

  1-溴甲基环丙烷-1,2-二羧酸二叔丁基酯（1a）在含有三乙基硅烷和二叔丁基过氧化物的环丙烷中光解得到4-亚甲基戊-2-基-1,5-二酸基团（3c） ，也由（1a），其顺式异构体（2b），2-叔丁基-2-溴-4-亚甲基戊二酸酯二叔丁基（3a）或2-叔丁基2-溴-甲基-3的处理制得-亚甲基琥珀酸酯（4b），具有氢化三苯锡；这些实验支持了通过蛋白结合的自由基作用于B 12依赖酶α-亚甲基戊二酸突变酶的机制。

  DOI：

  10.1039/c39890001483
• 作为产物：
  描述：

  重氮基乙酸叔丁酯 在 重水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以72%的产率得到α-deuterated tert-butyl diazoacetate
  参考文献：
  名称：

  Synthesis of Structure and Function Diverse α-D-Diazoacetates, α-D-Diazoacetamides, α-D-Diazoketones, and the Antibiotic α-D-Azaserine

  摘要：

  Using 0.1 mol% to 1 mol% potassium carbonate in an acetonitrile-deuterium oxide mixture acts as a 'privileged' reaction system, which at ambient temperature affords, via a one-pot-one-cycle procedure, alpha-D-diazoacetates, alpha-D-diazoacetamides, or alpha-D-diazoketones from the corresponding nondeuterated form. The protocol is inexpensive, employs readily available materials, does not require harsh reaction conditions, requires two hours for completion, and affords the desired products in good yields and with excellent levels of deuterium incorporation. Exemplifying our protocol the first isotope labelled synthesis of N-Boc-alpha-D-azaserine with >= 95% D-incorporation is reported.

  DOI：

  10.1055/s-0032-1318136

文献信息

• METHOD AND CATALYST FOR SYNTHESISING AZIRIDINE
  申请人：University of East Anglia

  公开号：US20150166478A1

  公开（公告）日：2015-06-18

  The present invention relates to methods of synthesising aziridines including isotopically labelled aziridines, said methods comprising contacting an imine or one or more precursors thereof with a diazo compound in the presence of a phosphoramide or a phosphoramide-derived catalyst. The present invention also relates to aziridines, modified aziridines and aziridine-derived compounds preparable by the aforementioned methods, and to phosphoramide or phosphoramide-derived catalysts suitable for use in such methods.

  本发明涉及合成环氧乙烷的方法，包括同位素标记的环氧乙烷，所述方法包括将亚胺或其一个或多个前体与重氮化合物在磷酰胺或磷酰胺衍生的催化剂存在下接触。本发明还涉及通过上述方法制备的环氧乙烷、改性环氧乙烷和环氧乙烷衍生化合物，以及适用于这种方法的磷酰胺或磷酰胺衍生的催化剂。
• [EN] METHOD AND CATALYST FOR SYNTHESISING AZIRIDINE<br/>[FR] PROCÉDÉ ET CATALYSEUR POUR LA SYNTHÈSE D'AZIRIDINE
  申请人：UNIV EAST ANGLIA

  公开号：WO2013179052A1

  公开（公告）日：2013-12-05

  The present invention relates to methods of synthesising aziridines including isotopically labelled aziridines, said methods comprising contacting an imine or one or more precursors thereof with a diazo compound in the presence of a phosphoramide or a phosphoramide-derived catalyst. The present invention also relates to aziridines, modified aziridines and aziridine-derived compounds preparable by the aforementioned methods, and to phosphoramide or phosphoramide-derived catalysts suitable for use in such methods.

  本发明涉及一种合成环丙胺的方法，包括同位素标记的环丙胺，所述方法包括在磷酰胺或磷酰胺衍生的催化剂存在下，将亚胺或其一个或多个前体与重氮化合物接触。本发明还涉及通过上述方法可制备的环丙胺、改性环丙胺和环丙胺衍生化合物，以及适用于此类方法的磷酰胺或磷酰胺衍生的催化剂。
• Synthesis of Structure and Function Diverse α-D-Diazoacetates, α-D-Diazoacetamides, α-D-Diazoketones, and the Antibiotic α-D-Azaserine
  作者：Sean Bew、Polly-Anna Ashford、Dominika Bachera

  DOI：10.1055/s-0032-1318136

  日期：——

  Using 0.1 mol% to 1 mol% potassium carbonate in an acetonitrile-deuterium oxide mixture acts as a 'privileged' reaction system, which at ambient temperature affords, via a one-pot-one-cycle procedure, alpha-D-diazoacetates, alpha-D-diazoacetamides, or alpha-D-diazoketones from the corresponding nondeuterated form. The protocol is inexpensive, employs readily available materials, does not require harsh reaction conditions, requires two hours for completion, and affords the desired products in good yields and with excellent levels of deuterium incorporation. Exemplifying our protocol the first isotope labelled synthesis of N-Boc-alpha-D-azaserine with >= 95% D-incorporation is reported.
• Model experiments pertaining to the mechanism of action of vitamin B₁₂-dependent α-methyleneglutarate mutase
  作者：Susan Ashwell、Alwyn G. Davies、Bernard T. Golding、Robyn Hay-Motherwell、Samson Mwesigye-Kibende

  DOI：10.1039/c39890001483

  日期：——

  Photolysis of di-t-butyl 1-bromomethylcyclopropane-1,2-dicarboxylate (1a) in cyclopropane containing triethylsilane and di-t-butyl peroxide gave the 4-methylenepent-2-yl-1,5-dioic acid radical (3c), which was also produced from treatment of (1a), its cis-isomer (2b), di-t-butyl-2-bromo-4-methyleneglutarate (3a), or di-t-butyl 2-bromo-methyl-3-methylenesuccinate (4b), with triphenyltin hydride; these

  1-溴甲基环丙烷-1,2-二羧酸二叔丁基酯（1a）在含有三乙基硅烷和二叔丁基过氧化物的环丙烷中光解得到4-亚甲基戊-2-基-1,5-二酸基团（3c） ，也由（1a），其顺式异构体（2b），2-叔丁基-2-溴-4-亚甲基戊二酸酯二叔丁基（3a）或2-叔丁基2-溴-甲基-3的处理制得-亚甲基琥珀酸酯（4b），具有氢化三苯锡；这些实验支持了通过蛋白结合的自由基作用于B 12依赖酶α-亚甲基戊二酸突变酶的机制。