N⁴-tert-butyl-phenylacetic acid thio-semicarbazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N⁴-tert-butyl-phenylacetic acid thio-semicarbazide
• 英文别名: 1-Tert-butyl-3-[(2-phenylacetyl)amino]thiourea
• 化学式: C₁₃H₁₉N₃OS
• 分子量: 265.379
• InChiKey: NVYWRBOMSSSNKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N⁴-tert-butyl-phenylacetic acid thio-semicarbazide 在 吡啶 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以78%的产率得到N-tert-butyl-(5-benzyl-[1,3,4]oxadiazol-2-yl)-amine
  参考文献：
  名称：

  Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazoles

  摘要：

  A facile and general protocol for the preparation of 2-amino-1,3,4- oxadiazoles is reported. This method relies on a tosyl chloride/pyridine-mediated cyclization of a thiosemicarbazide, which is readily prepared by acylation of a given hydrazide with the appropriate isothiocyanate. Cyclization of the thiosemicarbazide consistently outperforms the analogous semicarbazide cyclization under these conditions, for 18 distinct examples. Utilizing this protocol, we have prepared 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles in 78-99% yield.

  DOI：

  10.1021/jo0618730
• 作为产物：
  描述：

  叔丁基异硫氰酸酯 、 苯乙酸肼 以 四氢呋喃 为溶剂， 生成 N⁴-tert-butyl-phenylacetic acid thio-semicarbazide
  参考文献：
  名称：

  Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazoles

  摘要：

  A facile and general protocol for the preparation of 2-amino-1,3,4- oxadiazoles is reported. This method relies on a tosyl chloride/pyridine-mediated cyclization of a thiosemicarbazide, which is readily prepared by acylation of a given hydrazide with the appropriate isothiocyanate. Cyclization of the thiosemicarbazide consistently outperforms the analogous semicarbazide cyclization under these conditions, for 18 distinct examples. Utilizing this protocol, we have prepared 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles in 78-99% yield.

  DOI：

  10.1021/jo0618730

文献信息

• Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazoles
  作者：Sarah J. Dolman、Francis Gosselin、Paul D. O'Shea、Ian W. Davies

  DOI：10.1021/jo0618730

  日期：2006.12.1

  A facile and general protocol for the preparation of 2-amino-1,3,4- oxadiazoles is reported. This method relies on a tosyl chloride/pyridine-mediated cyclization of a thiosemicarbazide, which is readily prepared by acylation of a given hydrazide with the appropriate isothiocyanate. Cyclization of the thiosemicarbazide consistently outperforms the analogous semicarbazide cyclization under these conditions, for 18 distinct examples. Utilizing this protocol, we have prepared 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles in 78-99% yield.