thiophen-2-ylmethyl α-D-diazoacetate | 1438843-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: thiophen-2-ylmethyl α-D-diazoacetate
• 英文别名: thiophen-2-ylmethyl α-²H-diazoacetate；Thiophen-2-ylmethyl 2-deuterio-2-diazoacetate；thiophen-2-ylmethyl 2-deuterio-2-diazoacetate
• CAS: 1438843-20-9
• 化学式: C₇H₆N₂O₂S
• 分子量: 183.195
• InChiKey: SSNHAEBBQWMHMX-QYKNYGDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  thiophen-2-ylmethyl diazoacetate 在 重水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到thiophen-2-ylmethyl α-D-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