2,6-dibromophenyllithium | 507242-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dibromophenyllithium
• CAS: 507242-11-7
• 化学式: C₆H₃Br₂Li
• 分子量: 241.839
• InChiKey: JPFFPFITHWCLFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,6-dibromophenyllithium 在 正丁基锂 、 二异丙胺 、 四氯化硅 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以45%的产率得到
  参考文献：
  名称：

  2,6-二卤代苯基锂试剂对氯硅烷的反应性。2,3-和2,6-二卤代苯基（二）硅烷的合成与结构

  摘要：

  2,6-二卤代苯基锂2,6- X 2 C 6 H 3 Li（X = F，Cl，Br）与氯硅烷ClMe 2 SiSiCl 2 Me，SiCl 4和HSiCl 3反应得到二芳基乙硅烷（2,6 ‐ X 2 C 6 H 3 SiMe 2）2 [ X = F（1a），Cl（1b），Br（1c）]以及二芳基和三芳基硅烷（2,6‐ X 2 C 6 H 3）2 SiCl2 [ X = F（3a），Cl（3a）]，（2,3-Br 2 C 6 H 3）2 SiCl 2（4c），（2,6-F 2 C 6 H 3）3 SiH（6a）和（2,6 - X 2 C 6 H 3）2 Si（H）Cl [ X = Cl（7b），Br（7c）]。4c的形成在芳基锂异构体2,6-Br 2 C 6 H 3 Li和2,3-Br 2 C 6 H 3 Li之间存在平衡的基础上合理化。使用LiAlH 4还原3a，3b，4c，7b和7c可得到二芳基硅烷（2

  DOI：

  10.1002/zaac.201800196

文献信息

• METHODS FOR STABILIZING LITHIATED HALOGEN-SUBSTITUTED AROMATIC COMPOUNDS
  申请人：Ji Yaohui

  公开号：US20090118546A1

  公开（公告）日：2009-05-07

  The present invention provides novel methods for stabilizing lithiated halogen-substituted aromatic compounds. In particular, the method is useful for the preparation of 2-methoxy-5, 6-difluorobenzaldehyde, an important intermediate for the preparation of [4-amino-2-(1-methanesulfonylpiperidin-4-ylamino) pyrimidin-5-yl](2,3-difluoro-6methoxyphenyl)methanone, a potent and selective inhibitor of CDK4/Cyclin D1, CDK2/Cyclin E and CDK1/Cyclin B. The method is also useful for stabilizing other lithiated halogen-substituted aromatic compounds and is particularly useful for scale up reactions where the exothermic nature of the reaction can lead to reaction runway.

  本发明提供了一种稳定锂化卤代芳香化合物的新方法。特别是，该方法对于制备2-甲氧基-5,6-二氟苯甲醛非常有用，该化合物是制备[4-氨基-2-(1-甲磺酰基哌啶-4-基氨基)嘧啶-5-基](2,3-二氟-6-甲氧基苯基)甲酮的重要中间体，后者是CDK4 / Cyclin D1，CDK2 / Cyclin E和CDK1 / Cyclin B的有效选择性抑制剂。该方法还对于稳定其他锂化卤代芳香化合物非常有用，尤其适用于规模化反应，其中反应的放热性质可能导致反应失控。
• Ring opening of aziridines with ortho-bromophenyl metal reagents: synthesis of 2-substituted indolines
  作者：David J. Michaelis、Thomas A. Dineen

  DOI：10.1016/j.tetlet.2009.02.047

  日期：2009.4

  Stabilized ortho-bromo phenyllithium reagents, generated via lithium-halogen exchange of aryl iodides, undergo regioselective ring opening of mono-substituted N-Boc, N-Cbz, and N-tosyl-protected aziridines in good to excellent yields. The resulting ortho-bromo phenethylamines can be cyclized under transition-metal-catalyzed conditions to give 2-substituted chiral, non-racemic indolines in good yields. (C) 2009 Elsevier Ltd. All rights reserved.
• US7619123B2
  申请人：——

  公开号：US7619123B2

  公开（公告）日：2009-11-17
• [EN] METHODS FOR STABILIZING LITHIATED HALOGEN-SUBSTITUTED AROMATIC COMPOUNDS<br/>[FR] PROCÉDÉS DE STABILISATION DE COMPOSÉS AROMATIQUES LITHIÉS À SUBSTITUTION HALOGÈNE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009056487A1

  公开（公告）日：2009-05-07

  The present invention provides novel methods for stabilizing lithiated halogen-substituted aromatic compounds. In particular, the method is useful for the preparation of 2-methoxy-5, 6-difluorobenzaldehyde, an important intermediate for the preparation of [4-amino-2-(1-methanesuifonyrpiperidin-4-ylamino) pyrimidin-5-yl](2,3-difluoro- 6methoxyphenyl)methanone, a potent and selective inhibitor of CDK4/Cyclin D1, CDK2/Cyclin E and CDK1/Cyclin B. The method is also useful for stabilizing other lithiated halogen-substituted aromatic compounds and is particularly useful for scale up reactions where the exothermic nature of the reaction can lead to reaction runway. The reaction runaway hazard can be eliminated by using anhydrous MgCl2 as an additive to complex with and stabilize the reactive species and slow down the rate of decomposition.