(E)-t-butyl-4-(4-cyano-5-(2-nitrovinyl)thiophen-3-yl)phenyl-carbamate | 1150566-13-4

• 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: (E)-t-butyl-4-(4-cyano-5-(2-nitrovinyl)thiophen-3-yl)phenyl-carbamate
• 英文别名: N-[4-[4-(azaniumylidynemethyl)-5-[(E)-2-nitroethenyl]thiophen-3-yl]phenyl]-1-[(2-methylpropan-2-yl)oxy]methanimidate
• CAS: 1150566-13-4
• 化学式: C₁₈H₁₇N₃O₄S
• 分子量: 371.417
• InChiKey: VROUWSMRECFNCL-CMDGGOBGSA-N

物化性质

• 熔点：
  219-220 °C
• 沸点：
  519.9±50.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-t-butyl-4-(4-cyano-5-(2-nitrovinyl)thiophen-3-yl)phenyl-carbamate 在 3% Pt 0.6% V on carbon 、 氢气 、 亚膦酸 作用下， 以 四氢呋喃 、 水 为溶剂， 95.0 ℃ 、721.87 kPa 条件下， 反应 10.0h， 以77%的产率得到t-butyl-4-(4-aminothieno[3,2-c]pyridine-3-yl)phenylcarbamate
  参考文献：
  名称：

  Improved Synthesis of 3-Substituted-4-amino-[3,2-c]-thienopyridines

  摘要：

  Two syntheses of 3-substituted-4-amino-[3,2-c]thienopyridines have been developed to replace the standard literature route to these compounds, which uses unattractive conditions involving azide and high temperatures. The first synthesis utilizes a Friedel-Crafts reaction as its key ring-forming step, whereas the second route relies on an unprecedented intramolecular reductive cyclization between a nitroolefin and a nitrile as its key ring-forming step. The development and optimization of each 3-substituted-4amino-[3,2-c]thienopyridine synthesis is discussed and a comparison of the routes is presented.

  DOI：

  10.1021/jo9003772
• 作为产物：
  描述：

  硝基甲烷 、 t-butyl-4-(4-cyano-5-formylthiophen-3-yl)phenylcarbamate 在 4-二甲氨基吡啶 、 乙酸酐 作用下， 以 乙酸甲酯 为溶剂， 反应 3.25h， 以91%的产率得到(E)-t-butyl-4-(4-cyano-5-(2-nitrovinyl)thiophen-3-yl)phenyl-carbamate
  参考文献：
  名称：

  Improved Synthesis of 3-Substituted-4-amino-[3,2-c]-thienopyridines

  摘要：

  Two syntheses of 3-substituted-4-amino-[3,2-c]thienopyridines have been developed to replace the standard literature route to these compounds, which uses unattractive conditions involving azide and high temperatures. The first synthesis utilizes a Friedel-Crafts reaction as its key ring-forming step, whereas the second route relies on an unprecedented intramolecular reductive cyclization between a nitroolefin and a nitrile as its key ring-forming step. The development and optimization of each 3-substituted-4amino-[3,2-c]thienopyridine synthesis is discussed and a comparison of the routes is presented.

  DOI：

  10.1021/jo9003772

文献信息

• Improved Synthesis of 3-Substituted-4-amino-[3,2-<i>c</i>]-thienopyridines
  作者：Kenneth M. Engstrom、Amanda L. Baize、Thaddeus S. Franczyk、Jeffrey M. Kallemeyn、Mathew M. Mulhern、Robert C. Rickert、Seble Wagaw

  DOI：10.1021/jo9003772

  日期：2009.5.15

  Two syntheses of 3-substituted-4-amino-[3,2-c]thienopyridines have been developed to replace the standard literature route to these compounds, which uses unattractive conditions involving azide and high temperatures. The first synthesis utilizes a Friedel-Crafts reaction as its key ring-forming step, whereas the second route relies on an unprecedented intramolecular reductive cyclization between a nitroolefin and a nitrile as its key ring-forming step. The development and optimization of each 3-substituted-4amino-[3,2-c]thienopyridine synthesis is discussed and a comparison of the routes is presented.