ethyl N-(4-cyanomethyl)carbamate | 165615-78-1

• 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: ethyl N-(4-cyanomethyl)carbamate
• 英文别名: Carbamic acid, [4-(cyanomethyl)phenyl]-, ethyl ester；ethyl N-[4-(cyanomethyl)phenyl]carbamate
• CAS: 165615-78-1
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD16662042
• 分子量: 204.228
• InChiKey: IUSMEVOBKBQFSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl N-(4-cyanomethyl)carbamate 在 硝酸 、 乙酸酐 作用下， 反应 2.0h， 以68.4%的产率得到ethyl N-(4-cyanomethyl-2-nitrophenyl)carbamate
  参考文献：
  名称：

  Synthesis of a hexahydro-2H-imidazo[4,5-g]isoquinolin-2-one derivative as an isostere of catecholamine-based selective dopamine D-1 antagonists

  摘要：

  The synthesis of the racemic hexahydro-2H-imidazo [4,5-g] isoquinolin-2-one 15 (BW2247W94), a 6,7-ureylene isostere of the 6,7-dihydroxy-tetrahydroisoquinoline 1 (BW32C73), has been achieved in ten stages from 4-nitrobenzyl cyanide 5. The key step is a selective reduction of the nitrile 8 to the amine 9, in the presence of nitro and carbamate functional groups.

  DOI：

  10.1016/0040-4020(95)98702-j
• 作为产物：
  描述：

  对氨基苯乙腈 、 氯甲酸乙酯 在 三乙胺 作用下， 以 氯仿 为溶剂， 以59.8%的产率得到ethyl N-(4-cyanomethyl)carbamate
  参考文献：
  名称：

  Synthesis of a hexahydro-2H-imidazo[4,5-g]isoquinolin-2-one derivative as an isostere of catecholamine-based selective dopamine D-1 antagonists

  摘要：

  The synthesis of the racemic hexahydro-2H-imidazo [4,5-g] isoquinolin-2-one 15 (BW2247W94), a 6,7-ureylene isostere of the 6,7-dihydroxy-tetrahydroisoquinoline 1 (BW32C73), has been achieved in ten stages from 4-nitrobenzyl cyanide 5. The key step is a selective reduction of the nitrile 8 to the amine 9, in the presence of nitro and carbamate functional groups.

  DOI：

  10.1016/0040-4020(95)98702-j

文献信息

• Synthesis of a hexahydro-2H-imidazo[4,5-g]isoquinolin-2-one derivative as an isostere of catecholamine-based selective dopamine D-1 antagonists
  作者：Clive V Denyer、Hazel Bunyan、David M Loakes、Jacqueline Tucker、Janet Gillam

  DOI：10.1016/0040-4020(95)98702-j

  日期：1995.4

  The synthesis of the racemic hexahydro-2H-imidazo [4,5-g] isoquinolin-2-one 15 (BW2247W94), a 6,7-ureylene isostere of the 6,7-dihydroxy-tetrahydroisoquinoline 1 (BW32C73), has been achieved in ten stages from 4-nitrobenzyl cyanide 5. The key step is a selective reduction of the nitrile 8 to the amine 9, in the presence of nitro and carbamate functional groups.