N-benzyl-3-nitrothiophen-2-amine | 186808-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: N-benzyl-3-nitrothiophen-2-amine
• 英文别名: benzyl-(3-nitro-thiophen-2-yl)-amine
• CAS: 186808-45-7
• 化学式: C₁₁H₁₀N₂O₂S
• mdl: MFCD00099935
• 分子量: 234.279
• InChiKey: WGIWMLUJLWMJOL-UHFFFAOYSA-N

物化性质

• 沸点：
  403.5±35.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-nitrothiophen-2-amine 在 铁粉 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 48.0h， 生成 8-benzyl-4H-thieno<2,3-b><1,4>diazepine-5,7(6H,8H)-dione
  参考文献：
  名称：

  Synthesis of Novel 5,6,7,8-Tetrahydro-4H-thieno[2,3-b][1,4]diazepine Derivatives

  摘要：

  Unsubstituted 5,6,7, 8-tetrahydro-4H-thieno[2, 3-b][1,4]diazepine (1) and 4H-thieno[2,3-b][1,4]diazepine-5,7(6H,8H)-dione (2) were newly synthesized. Benzoylation of 1 regioselectively afforded thienodiazepine (13) substituted with a benzoyl group nl position 4. Alternatively, novel synthetic procedures were devised to yield thienodiazepine (22) substituted with an alkyl group or compound (14) with an aralkyl group at position 8. Thus, the ingenious introduction of functional groups at the N-4 or 8 position of a thienodiazepine skeleton was achieved and then a variety of 5,6,7,8-tetrahydro-4H-thieno[2,3-b][1,4]diazepines (5)-(9), and (27), some of which exhibited potent arginine vasopressin antagonistic activity, were obtained using the key intermediates and (1), (13), (14) and (22).

  DOI：

  10.3987/com-98-8179
• 作为产物：
  描述：

  苄胺 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 N-benzyl-3-nitrothiophen-2-amine
  参考文献：
  名称：

  An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

  摘要：

  一种新的合成3-硝基-N-芳基/烷基噻吩-2-胺的协议，从α-硝基酮N，S-芳基/烷基氨基乙醛和1,4-二硫代-2,5-二醇与K2CO3存在下在回流乙醇中反应中获得良好产率。这种转化在单次操作中生成两个C-C键，可能通过包含2-巯基乙醛生成、亲核羰基加成、环合和消除步骤的反应序列进行。

  DOI：

  10.3762/bjoc.11.185

文献信息

• Consiglio, Giovanni; Frenna, Vincenzo; Mezzina, Elisabetta, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 2, p. 325 - 333
  作者：Consiglio, Giovanni、Frenna, Vincenzo、Mezzina, Elisabetta、Pizzolato, Antonio、Spinelli, Domenico

  DOI：——

  日期：——
• Synthesis of Novel 5,6,7,8-Tetrahydro-4H-thieno[2,3-b][1,4]diazepine Derivatives
  作者：Hidetsura Cho、Kengo Murakami、Akitaka Fujisawa、Misako Niwa、Hiroyuki Nakanishi、Itsuo Uchida

  DOI：10.3987/com-98-8179

  日期：——

  Unsubstituted 5,6,7, 8-tetrahydro-4H-thieno[2, 3-b][1,4]diazepine (1) and 4H-thieno[2,3-b][1,4]diazepine-5,7(6H,8H)-dione (2) were newly synthesized. Benzoylation of 1 regioselectively afforded thienodiazepine (13) substituted with a benzoyl group nl position 4. Alternatively, novel synthetic procedures were devised to yield thienodiazepine (22) substituted with an alkyl group or compound (14) with an aralkyl group at position 8. Thus, the ingenious introduction of functional groups at the N-4 or 8 position of a thienodiazepine skeleton was achieved and then a variety of 5,6,7,8-tetrahydro-4H-thieno[2,3-b][1,4]diazepines (5)-(9), and (27), some of which exhibited potent arginine vasopressin antagonistic activity, were obtained using the key intermediates and (1), (13), (14) and (22).
• An efficient synthesis of N-substituted 3-nitrothiophen-2-amines
  作者：Sundaravel Vivek Kumar、Shanmugam Muthusubramanian、J Carlos Menéndez、Subbu Perumal

  DOI：10.3762/bjoc.11.185

  日期：——

  A novel protocol for the synthesis of 3-nitro-N-aryl/alkylthiophen-2-amines in good yields from the reaction of α-nitroketene N,S-aryl/alkylaminoacetals and 1,4-dithiane-2,5-diol in the presence of K₂CO₃ in refluxing ethanol is described. This transformation generates two C–C bonds in a single operation and presumably proceeds through a reaction sequence comprising 2-mercaptoacetaldehyde generation, nucleophilic carbonyl addition, annelation and elimination steps.

  一种新的合成3-硝基-N-芳基/烷基噻吩-2-胺的协议，从α-硝基酮N，S-芳基/烷基氨基乙醛和1,4-二硫代-2,5-二醇与K2CO3存在下在回流乙醇中反应中获得良好产率。这种转化在单次操作中生成两个C-C键，可能通过包含2-巯基乙醛生成、亲核羰基加成、环合和消除步骤的反应序列进行。