1-benzyloxymethyl-4,5-diiodo-1H-imidazole | 134420-43-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1-benzyloxymethyl-4,5-diiodo-1H-imidazole
• 英文别名: 1-(benzyloxy)methyl-4,5-diiodoimidazole；4,5-Diiodo-1-(phenylmethoxymethyl)imidazole
• CAS: 134420-43-2
• 化学式: C₁₁H₁₀I₂N₂O
• 分子量: 440.022
• InChiKey: KAQONOISTFBSFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyloxymethyl-4,5-diiodo-1H-imidazole 在 bis-triphenylphosphine-palladium(II) chloride manganese(IV) oxide 、 copper(l) iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (1-benzenesulfonyl-6-benzyloxy-1H-indol-3-yl)-[4-(1-benzenesulfonyl-1H-indol-3-yl)-1-benzyloxymethyl-1H-imidazol-2-yl]-methanone
  参考文献：
  名称：

  海洋双吲哚生物碱的三组分偶联方法：托普汀，脱氧托普汀和溴青霉素

  摘要：

  描述了托普汀家族的三种海洋双吲哚生物碱（1、2、4）的总合成以及非天然脱氧溴青霉素（33）的合成。键元件包括1,2-加成氧化序列来构造双- heteroarylketones（18，19，29，30），并涉及3- stannylindoles一个Pd催化的杂芳基化（12，26）

  DOI：

  10.1016/0040-4039(96)01148-3
• 作为产物：
  描述：

  1-<(Benzyloxy)methyl>-2,4,5-triiodoimidazole 在 正丁基锂 作用下， 以99%的产率得到1-benzyloxymethyl-4,5-diiodo-1H-imidazole
  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

文献信息

• Convenient access to bis-indole alkaloids. Application to the synthesis of topsentins
  作者：Sajal K. Mal、Luis Bohé、Saïd Achab

  DOI：10.1016/j.tet.2008.04.045

  日期：2008.6

  Topsentins and related bis-indole alkaloids may be efficiently synthesized through an addition/oxidation sequence leading to 2-(3-indolylcarbonyl)-imidazole derivatives followed by a Pd-catalyzed heteroarylation with the appropriate 3-stannylindoles.

  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。
• Polyfunctionalisation of imidazole via sequential imidazolyl anion formation
  作者：David S. Carver、Stephen D. Lindell、Elizabeth A. Saville-Stones

  DOI：10.1016/s0040-4020(97)00939-3

  日期：1997.10

  A method for achieving the sequential functionalisation of the imidazole ring in the order C-5-->C-4-->C-2 is described. The chemistry proceeds via the regioselective formation of positionally stable imidazolyl anions which are reacted with electrophiles (aldehydes, alkyl halides, azides, formamides, isocyanates) to afford substituted imidazoles in 31-90% yield. (C) 1997 Elsevier Science Ltd.
• 5-Substituted Imidazole-4-acetic Acid Analogues:  Synthesis, Modeling, and Pharmacological Characterization of a Series of Novel γ-Aminobutyric Acid_C Receptor Agonists
  作者：Christian Madsen、Anders A. Jensen、Tommy Liljefors、Uffe Kristiansen、Birgitte Nielsen、Camilla P. Hansen、Mogens Larsen、Bjarke Ebert、Benny Bang-Andersen、Povl Krogsgaard-Larsen、Bente Frølund

  DOI：10.1021/jm070447j

  日期：2007.8.1

  A series of ring-substituted analogues of imidazole-4-acetic acid (IAA, 4), a partial agonist at both GABA(A) and GABA(C) receptors (GABA = gamma-aminobutyric acid), have been synthesized. The synthesized compounds 8a-1 have been evaluated as ligands for the alpha(1)beta(2)gamma(2S) GABA(A) receptors and the rho(1) GABA(C) receptors using the FLIPR membrane potential (FMP) assay and by electrophysiology techniques. None of the tested compounds displayed activity at the GABA(A) receptors at concentrations up to 1000 mu M. However, the 5-Me, 5-Ph, 5-p-Me-Ph, and 5-p-F-Ph IAA analogues, 8a,c,f,g, displayed full agonist activities at the rho(1) receptors in the FMP assay (EC50 in the range 22-420 mu M). Ligand-protein docking identified the Thr129 in the alpha(1) subunit and the corresponding Ser168 residue in rho(1) as determinants of the selectivity displayed by the 5-substituted IAA analogues. The fact that GABA, 4, and 8a displayed decreased agonist potencies at a rho(1)Ser168Thr mutant compared to the WT rho(1) receptor strongly supported this hypothesis. However, in contrast to GABA and 4, which exhibited increased agonist potencies at a alpha(1)(Thr129Ser)beta(2)gamma(2) mutant compared to WT GABA(A) receptor, the data obtained for 8a at the WT and mutant receptors were nonconclusive.
• GROZIAK, MICHAEL P.;WEI, LULIN, J. ORG. CHEM., 56,(1991) N3, C. 4296-4300
  作者：GROZIAK, MICHAEL P.、WEI, LULIN

  DOI：——

  日期：——

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