1-<(benzyloxy)methyl>-4-iodoimidazole-2-carboxaldehyde | 134420-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-<(benzyloxy)methyl>-4-iodoimidazole-2-carboxaldehyde
• 英文别名: 4-Iodo-1-(phenylmethoxymethyl)imidazole-2-carbaldehyde
• CAS: 134420-46-5
• 化学式: C₁₂H₁₁IN₂O₂
• 分子量: 342.136
• InChiKey: DKSWBKORYCKEKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1-<(benzyloxy)methyl>-4-iodoimidazole-2-carboxaldehyde 在 羟胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以93%的产率得到(Z)-1-<(benzyloxy)methyl>-4-iodoimidazole-2-carboxaldehyde oxime
  参考文献：
  名称：

  Regioselective formation of imidazol-2-yllithium, imidazol-4-yllithium, and imidazol-5-yllithium species

  摘要：

  Representative imidazol-2-yllithium, imidazol-4-yllithium, and imidazol-5-yllithium species have been prepared via halogen-metal exchange, and the propensity of the latter two to undergo isomerization and quench by electrophilic reagents has been studied. The C2-unsubstituted imidazol-5-yllithium species 3 is generated within 10 min at -78-degrees-C from 1-[(benzyloxy)methyl]-4,5-diiodoimidazole (1b) and affords the C5-formyl product 4 upon reaction with DMF, but gives the isomeric C2-formyl product 6 if allowed to equilibrate to the imidazol-2-yllithium species 5 for an additional 35 min at -78-degrees-C before quench. The less reactive electrophile diethyl carbonate is unable to trap 3 and instead reacts with 5 to afford tris[1-[(benzyloxy)methyl]-4-iodo-2-imidazolyl]carbinol (7). In contrast, 1-[(benzyloxy)methyl]-4-iodoimidazole-5-carboxaldehyde ethylene acetal (10) metalates to give the C2-unsubstituted imidazol-4-yllithium species 13, which undergoes a very rapid conversion to its imidazol-2-yllithium isomer 14, even at -100-degrees-C, giving the 2,5-dicarboxaldehyde 5-ethylene acetal 16 or the 2-deuterio-5-carboxaldehyde ethylene acetal 15 upon quench with DMF or D2O, respectively. Thus, in the presence of C2 unsubstitution, C5 functionalization could be accomplished when the electrophile was sufficiently reactive, while C4 functionalization could not. Short- and long-range H-1-C-13 heteronuclear (Hector) 2D NMR spectroscopic analyses were instrumental in the structural assignments of key compounds.

  DOI：

  10.1021/jo00013a042
• 作为产物：
  描述：

  1-benzyloxymethyl-4,5-diiodo-1H-imidazole 、 N,N-二甲基甲酰胺 在 正丁基锂 、 ammonium chloride 、 水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 0.75h， 以72%的产率得到1-<(benzyloxy)methyl>-4-iodoimidazole-2-carboxaldehyde
  参考文献：
  名称：

  方便获得双吲哚生物碱。在topsentins合成中的应用

  摘要：

  可以通过加成/氧化序列有效合成Topsentins和相关的双吲哚生物碱，生成2-（3-吲哚基羰基）-咪唑衍生物，然后通过Pd催化与适当的3-stannylindoldols进行杂芳基化反应。

  DOI：

  10.1016/j.tet.2008.04.045

文献信息

• [EN] 6,7-DIHYDROPYRAZOLO[1,5-α]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS<br/>[FR] COMPOSÉS DE 6,7-DIHYDROPYRAZOLO[1,5-Α]PYRAZIN-4(5H)-ONE ET LEUR UTILISATION COMME MODULATEURS ALLOSTÉRIQUES NÉGATIFS DES RÉCEPTEURS MGLUR2
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2016087487A1

  公开（公告）日：2016-06-09

  The present invention relates to novel 6,7-dihydropyrazolo[1,5-α]pyrazin-4(5H)-one derivatives as negative allosteric modulators (NAMs) of the metabotropic glutamate receptor subtype 2 ("mGluR2"). The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention or treatment of disorders in which the mGluR2 subtype of metabotropic receptors is involved.

  本发明涉及作为代谢型谷氨酸受体亚型2 ("mGluR2") 的负变构调节剂 (NAMs) 的新型6,7-二氢吡唑并[1,5-α]吡嗪-4(5H)-酮衍生物。该发明还涉及包含这种化合物的药物组合物，用于制备这种化合物和组合物的方法，以及用于预防或治疗涉及代谢型受体的 mGluR2 亚型的疾病的这种化合物和组合物的用途。
• GROZIAK, MICHAEL P.;WEI, LULIN, J. ORG. CHEM., 56,(1991) N3, C. 4296-4300
  作者：GROZIAK, MICHAEL P.、WEI, LULIN

  DOI：——

  日期：——
• 6,7-DIHYDROPYRAZOLO[1,5- ]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLU2 RECEPTORS
  申请人：Janssen Pharmaceutica NV

  公开号：EP3227295B1

  公开（公告）日：2019-02-20
• 6,7-DIHYDROPYRAZOLO[1,5-a]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
  申请人：Janssen Pharmaceutical NV

  公开号：US20170369493A1

  公开（公告）日：2017-12-28

  The present invention relates to novel 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives as negative allosteric modulators (NAMs) of the metabotropic glutamate receptor subtype 2 (“mGluR2”). The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention or treatment of disorders in which the mGluR2 subtype of metabotropic receptors is involved.

表征谱图