2-lithio-N-methylimidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-lithio-N-methylimidazole
• 化学式: C₃H₃LiN₂
• 分子量: 74.0112
• InChiKey: UVHPQDAOCIMGID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  6.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.68
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-lithio-N-methylimidazole 、 7-((1,1'-biphenyl)-4-yloxy)heptanal 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Heterocyclic ketones as inhibitors of histone deacetylase

  摘要：

  Several heterocyclic ketones were investigated as potential inhibitors of histone deacetylase. Nanomolar inhibitors such as 22 and 25 were obtained, the anti-proliferative activity of which were shown to be mediated by HDAC inhibition. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2003.09.007

文献信息

• Stereocontrol by diethylaluminum chloride in the addition of 2-lithiofuran and N-methyl-2-lithioimidazole to α-alkoxy nitrones. Total synthesis of 5-O-carbamoylpolyoxamic acid.
  作者：Alessandro Dondoni、Santiago Franco、Francisco Luis Merchán、Pedro Merino、Tomás Tejero

  DOI：10.1016/s0040-4039(00)73939-6

  日期：1993.1

  derived from D-glyceraldehyde acetonide leads to the corresponding syn-adducts as major products (ds 88–96 %) while the reaction in the presence of Et2AlCl leads to anti isomers (ds 79–95 %); the synthesis of 5-O-carbamoylpolyoxamic acid from 4-O-benzyl-2,3-O-isopropylidene-L-threose via the nitrone-furan adduct is described

  在衍生自D-甘油醛丙酮化物的硝酮2中添加标题金属化杂环1会导致相应的正加合物作为主要产物（ds 88–96％），而在Et 2 AlCl存在下的反应会导致反异构体（ ds 79–95％）；描述了通过硝基-呋喃加合物由4-O-苄基-2,3-O-异亚丙基-L-苏糖合成5-O-氨基甲酰基聚乙酰胺酸
• Design of novel and potent cPLA2α inhibitors containing an α-methyl-2-ketothiazole as a metabolically stable serine trap
  作者：Antonio Mete、Glen Andrews、Mike Bernstein、Stephen Connolly、Paul Hartopp、Clive G. Jackson、Richard Lewis、Iain Martin、David Murray、Rob Riley、David H. Robinson、Gill M. Smith、Edward Wells、W. John Withnall

  DOI：10.1016/j.bmcl.2011.03.005

  日期：2011.5

  We report the design of novel, potent cPLA(2)alpha inhibitors that possess an alpha-methyl-2-ketothiazole that acts as a serine-reactive moiety. We describe the optimization of the series for potency and metabolic stability towards ketone reduction. This was achieved by attenuating the reactivity of the ketone using a combination of electronic and steric effects. (C) 2011 Elsevier Ltd. All rights reserved.