2-(二甲氧基甲基)-1H-咪唑 | 112655-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(二甲氧基甲基)-1H-咪唑
• 中文别名: 咪唑-2-羧醛二甲基乙缩醛
• 英文名称: 2-(dimethoxymethyl)imidazole
• 英文别名: 2-(dimethoxymethyl)-1H-imidazole
• CAS: 112655-19-3
• 化学式: C₆H₁₀N₂O₂
• mdl: MFCD03093091
• 分子量: 142.158
• InChiKey: DSSLAGQNEMWAEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  2-(二甲氧基甲基)-1H-咪唑 在 正丁基锂 作用下， 反应 1.0h， 生成 2-(dimethoxymethyl)-3-(1-ethoxyethyl)imidazole-4-carbaldehyde
  参考文献：
  名称：

  1-(1-Ethoxyethyl): an effective protecting group for imidazole nitrogen

  摘要：

  DOI：

  10.1021/jo00240a038
• 作为产物：
  描述：

  甲醇 、 2-咪唑甲醛 在 硫酸 作用下， 反应 24.0h， 以80%的产率得到2-(二甲氧基甲基)-1H-咪唑
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 5. Structure-activity relationships for side-chain nitro-, sulfone-, amino-, and aminosulfonyl-substituted analogs for therapy against anticholinesterase intoxication

  摘要：

  Several quaternary imidazolium oxime derivatives incorporating side chains bearing nitro, sulfone, amino, and aminosulfonyl substituents were prepared and evaluated as treatment therapeutics for anti-AChE intoxication. In vivo test results in the mouse revealed that many of these compounds are highly effective in providing life-saving protection against the extremely toxic cholinesterase inhibitors soman and tabun. Several structure-activity relationships were noted that were characteristic of the side-chain substituent. In vivo test results for additional selected derivatives of some of the more therapeutically active compounds indicated that the quaternary heteroaryl nucleus is essential for activity whereas a nucleophilic moiety (i.e., oxime) is not. In support of previous suspicions, these results afforded additional evidence suggesting that reactivation is not the main mode of antidotal action by the imidazolium oximes. An alternative antidotal mechanism is postulated that is consistent with all data and that involves enzyme protection by the compounds.

  DOI：

  10.1021/jm00108a020

文献信息

• RNA Control by Photoreversible Acylation
  作者：Willem A. Velema、Anna M. Kietrys、Eric T. Kool

  DOI：10.1021/jacs.7b12408

  日期：2018.3.14

  rely on fully synthetic nucleic acids with photocaged nucleobases, limiting application to relatively short synthetic RNAs. Here we report a method to gain photocontrol over RNA by postsynthetic acylation of 2'-hydroxyls with photoprotecting groups. One-step introduction of these groups efficiently blocks hybridization, which is restored after light exposure. Polyacylation (termed cloaking) enables

  RNA 功能的外部光控制已成为研究核酸生物学的有用工具。大多数当前方法依赖于具有光笼化核碱基的全合成核酸，限制了对相对较短的合成 RNA 的应用。在这里，我们报告了一种通过 2'-羟基与光保护基团的合成后酰化来获得对 RNA 的光控制的方法。这些基团的一步引入有效地阻止了杂交，在光照后恢复。多酰化（称为隐形）可以控制锤头状核酶，说明 RNA 催化功能的光学控制。在转录的 237 nt RNA 适配体上使用新方法证明了这种方法在细胞环境中开启 RNA 折叠的效用，并强调了在生物学研究中的应用潜力。
• Preparation process for 2 formyl imidazole acetals
  申请人：Societe Francaise Hoechst

  公开号：US05550250A1

  公开（公告）日：1996-08-27

  Preparation process for a product of formula (I): ##STR1## in which R.sub.1 and R.sub.2, either are identical and represent a C.sub.1 -C.sub.4 alkyl radical, or form together a group of formula (II): --CHR.sub.3 .paren open-st.CR.sub.4 R.sub.5 .paren close-st..sub.n CHR.sub.6 -- (II) in which R.sub.3, R.sub.4, R.sub.5 and R.sub.6, identical or different, represent a hydrogen atom or a C.sub.1 -C.sub.4 alkyl radical, and n represents 0 or 1, in which an aqueous mixture of glyoxal and an ethanal of formula (III): ##STR2## in which R.sub.1 and R.sub.2 have the meaning given above, is reacted with ammonia.

  公式（I）的产品制备过程：##STR1## 其中R1和R2要么相同且表示C1-C4烷基，要么一起形成式（II）的基团：--CHR3(paren open-st.CR4R5)paren close-st..sub.nCHR6--(II) 其中R3、R4、R5和R6相同或不同，表示氢原子或C1-C4烷基，n表示0或1，在其中将乙醛的水溶液与式（III）的乙醛反应，并加入氨。
• MANOHARAN, T. S.;BROWN, R. S., J. ORG. CHEM., 53,(1988) N 5, 1107-1110
  作者：MANOHARAN, T. S.、BROWN, R. S.

  DOI：——

  日期：——
• US5550250A
  申请人：——

  公开号：US5550250A

  公开（公告）日：1996-08-27
• Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 5. Structure-activity relationships for side-chain nitro-, sulfone-, amino-, and aminosulfonyl-substituted analogs for therapy against anticholinesterase intoxication
  作者：Gary A. Koolpe、Steven M. Lovejoy、Dane A. Goff、Kuei Ying Lin、Doris S. Leung、Clifford D. Bedford、Ralph N. Harris、H. A. Musallam、Irwin Koplovitz

  DOI：10.1021/jm00108a020

  日期：1991.4

  Several quaternary imidazolium oxime derivatives incorporating side chains bearing nitro, sulfone, amino, and aminosulfonyl substituents were prepared and evaluated as treatment therapeutics for anti-AChE intoxication. In vivo test results in the mouse revealed that many of these compounds are highly effective in providing life-saving protection against the extremely toxic cholinesterase inhibitors soman and tabun. Several structure-activity relationships were noted that were characteristic of the side-chain substituent. In vivo test results for additional selected derivatives of some of the more therapeutically active compounds indicated that the quaternary heteroaryl nucleus is essential for activity whereas a nucleophilic moiety (i.e., oxime) is not. In support of previous suspicions, these results afforded additional evidence suggesting that reactivation is not the main mode of antidotal action by the imidazolium oximes. An alternative antidotal mechanism is postulated that is consistent with all data and that involves enzyme protection by the compounds.