Methyl 1-benzyl-5-phenylimidazole-4-carboxylate | 119826-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methyl 1-benzyl-5-phenylimidazole-4-carboxylate
• CAS: 119826-01-6
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: KLINULQNLFJURN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 1-benzyl-5-phenylimidazole-4-carboxylate 在 sodium hydroxide 、 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 22.5h， 生成 2-[(1-benzyl-5-phenylimidazol-2-yl)sulfinylmethyl]-N,N-dimethylaniline
  参考文献：
  名称：

  2-[（2-氨基苄基）亚磺酰基] -1-（2-吡啶基）-1,4,5,6-四氢环戊[d]咪唑类是一类新型的胃H + / K + -ATPase抑制剂。

  摘要：

  合成了2-亚磺酰咪唑类化合物，并研究了其作为胃H + / K（+）-ATPase的潜在抑制剂。发现4,5-未取代的咪唑系列6-11和1,4,5,6-四氢环戊[d]咪唑系列12是酸分泌酶H + / K（+）-ATPase的有效抑制剂。结构-活性关系表明，在咪唑部分的1位上取代了2-吡啶基，并在2位上结合了（2-氨基苄基）-亚磺酰基，导致了具有良好化学稳定性的高活性化合物。咪唑部分中的其他取代方式导致生物活性降低。选择了2-[（2-氨基苄基）亚磺酰基] -1- [2-（3-甲基吡啶基）]-1,4,5,6-四氢环戊++ ++ ++ [d]-咪唑（12h，T-776）作为潜在的临床候选者进行进一步开发。

  DOI：

  10.1021/jm950610n
• 作为产物：
  描述：

  (Z)-Methyl 3-bromo-2-isocyano-3-phenylacrylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 Methyl 1-benzyl-5-phenylimidazole-4-carboxylate
  参考文献：
  名称：

  A Novel Synthesis of Methyl 1,5-Disubstituted Imidazole-4-carboxylates Using 3-Bromo-2-isocyanoacrylates (BICA)

  摘要：

  Methyl 1,5-disubstituted imidazole-4-carboxylates 1 were synthesised using methyl 3-substituted 3-bromo-2-isocyanoacrylates 3 (BICA), and the reaction mechanism was elucidated. Reactions of 3, which were prepared by bromination of 3-substituted 2-(formylamino)acrylates 6 followed by dehydration of the formylamino group, with a variety of primary amines gave imidazoles 1 in good overall yields. A mechanistic study suggested a Michael reaction of an amine with 3 followed by p-elimination of hydrogen bromide exclusively afforded (E)-N,3-disubstituted 3-amino-2-isocyanoacrylates 2. Geometric isomerization to (Z)-2 with a base and subsequent cyclization gave imidazoles 1.

  DOI：

  10.1021/jo00104a018

文献信息

• Synthesis of β-functionalized α, β-dehydroamino acid derivatives
  作者：Ken-ichi Nunami、Kiwamu Hiramatsu、Kimiaki Hayashi、Kazuo Matsumoto

  DOI：10.1016/s0040-4020(01)86052-x

  日期：1988.1

  β-Functionalized α,β-unsaturated amino acids were synthesized by an addition-elimination pathway. Reaction of methyl β-bromo-α-formylaminoacrylates (3a-e), which were prepared by the condensation of methyl isocyanoacetate (1) with aldehydes followed by bromination, with thiols gave β-alkylthio-α, β-unsaturated amino acid derivatives (6a-f). The reaction of (3a) with sodium azide resulted in the formation

  通过加成消除途径合成了β-官能化的α，β-不饱和氨基酸。通过将异氰基乙酸甲酯（1）与醛缩合，然后溴化与硫醇反应制得的β-溴-α-甲酰基氨基丙烯酸甲酯（3a-e）反应，得到β-烷硫基-α，β-不饱和氨基酸衍生物（ 6a-f）。（3a）与叠氮化钠的反应导致形成2-氧代咪唑啉衍生物（4）。另一方面，通过由（3a和3d），分别用苄醇和苄胺，然后进行酸性水合。
• A Facile Synthesis of Methyl 1,5-Disubstituted Imidazole-4-carboxylates
  作者：Kiwamu Hiramatsu、Ken-ichi Nunami、Kimiaki Hayashi、Kazuo Matsumoto

  DOI：10.1055/s-1990-27013

  日期：——

  Various methyl 1,5-disubstituted imidazole-4-carboxylates are synthesized by the reaction of methyl 3-bromo-2-isocyanoacrylates with a variety of primary amines in the presence of triethylamine.

  在三乙胺存在下，3-溴-2-异氰基丙烯酸甲酯与多种伯胺发生反应，合成出各种 1,5-二取代咪唑-4-羧酸甲酯。
• 2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6-tetrahydrocyclopent[<i>d</i>]imidazoles as a Novel Class of Gastric H⁺/K⁺-ATPase Inhibitors
  作者：Masaki Yamada、Takeshi Yura、Masamichi Morimoto、Tsunehiro Harada、Koichiro Yamada、Yasushi Honma、Mine Kinoshita、Masaki Sugiura

  DOI：10.1021/jm950610n

  日期：1996.1.1

  Substituted 2-sulfinylimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K(+)-ATPase. The 4,5-unsubstituted imidazole series 6-11 and the 1,4,5,6-tetrahydrocyclopent[d]imidazole series 12 were found to be potent inhibitors of the acid secretory enzyme H+/K(+)-ATPase. Structure-activity relationships indicate that the substitution of 2-pyridyl groups at the 1-position

  合成了2-亚磺酰咪唑类化合物，并研究了其作为胃H + / K（+）-ATPase的潜在抑制剂。发现4,5-未取代的咪唑系列6-11和1,4,5,6-四氢环戊[d]咪唑系列12是酸分泌酶H + / K（+）-ATPase的有效抑制剂。结构-活性关系表明，在咪唑部分的1位上取代了2-吡啶基，并在2位上结合了（2-氨基苄基）-亚磺酰基，导致了具有良好化学稳定性的高活性化合物。咪唑部分中的其他取代方式导致生物活性降低。选择了2-[（2-氨基苄基）亚磺酰基] -1- [2-（3-甲基吡啶基）]-1,4,5,6-四氢环戊++ ++ ++ [d]-咪唑（12h，T-776）作为潜在的临床候选者进行进一步开发。
• A Novel Synthesis of Methyl 1,5-Disubstituted Imidazole-4-carboxylates Using 3-Bromo-2-isocyanoacrylates (BICA)
  作者：Ken-ichi Nunami、Masaki Yamada、Toshio Fukui、Kazuo Matsumoto

  DOI：10.1021/jo00104a018

  日期：1994.12

  Methyl 1,5-disubstituted imidazole-4-carboxylates 1 were synthesised using methyl 3-substituted 3-bromo-2-isocyanoacrylates 3 (BICA), and the reaction mechanism was elucidated. Reactions of 3, which were prepared by bromination of 3-substituted 2-(formylamino)acrylates 6 followed by dehydration of the formylamino group, with a variety of primary amines gave imidazoles 1 in good overall yields. A mechanistic study suggested a Michael reaction of an amine with 3 followed by p-elimination of hydrogen bromide exclusively afforded (E)-N,3-disubstituted 3-amino-2-isocyanoacrylates 2. Geometric isomerization to (Z)-2 with a base and subsequent cyclization gave imidazoles 1.