t-butyl 2,5-dibromobenzoate | 861882-69-1

• 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: t-butyl 2,5-dibromobenzoate
• 英文别名: Tert-butyl 2,5-dibromobenzoate
• CAS: 861882-69-1
• 化学式: C₁₁H₁₂Br₂O₂
• 分子量: 336.023
• InChiKey: PHSDBYXWXFAYPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  324.7±22.0 °C(Predicted)
• 密度：
  1.605±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  t-butyl 2,5-dibromobenzoate 在 palladium on activated charcoal 四(三苯基膦)钯 、 盐酸羟胺 、 氢气 、 溶剂黄146 、 达卡巴嗪 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [5-(tert-Butoxycarbonylamino-imino-methyl)-2-(tert-butoxycarbonylamino-methyl)-benzoylamino]-acetic acid
  参考文献：
  名称：

  Structure-based design and synthesis of pyrazinones containing novel P1 ‘side pocket’ moieties as inhibitors of TF/VIIa

  摘要：

  We describe the structure-based design, synthesis, and enzymatic activity of a series of substituted pyrazinones as inhibitors of the TF/VIIa complex. These inhibitors contain substituents meta to the P(1) amidine designed to explore additional interactions with the VIIa residues in the so-called 'S(1) side pocket'. A crystal structure of the designed inhibitors demonstrates the ability of the P(1) side pocket moiety to engage Lys192 and main chain of Gly216 via hydrogen bond interactions, thus, providing additional possibility for chemical modification to improve selectivity and/or physical properties of inhibitors.

  DOI：

  10.1016/j.bmcl.2005.04.037
• 作为产物：
  描述：

  2,5-二溴苯甲酸 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到t-butyl 2,5-dibromobenzoate
  参考文献：
  名称：

  Structure-based design and synthesis of pyrazinones containing novel P1 ‘side pocket’ moieties as inhibitors of TF/VIIa

  摘要：

  We describe the structure-based design, synthesis, and enzymatic activity of a series of substituted pyrazinones as inhibitors of the TF/VIIa complex. These inhibitors contain substituents meta to the P(1) amidine designed to explore additional interactions with the VIIa residues in the so-called 'S(1) side pocket'. A crystal structure of the designed inhibitors demonstrates the ability of the P(1) side pocket moiety to engage Lys192 and main chain of Gly216 via hydrogen bond interactions, thus, providing additional possibility for chemical modification to improve selectivity and/or physical properties of inhibitors.

  DOI：

  10.1016/j.bmcl.2005.04.037

文献信息

• Highly selective and efficient conversion of aryl bromides to t-butyl benzoates with di-t-butyl dicarbonate
  作者：Hongmei Li、Jaume Balsells

  DOI：10.1016/j.tetlet.2007.12.134

  日期：2008.3

  t-Butyl benzoates can be accessed from aromatic compounds bearing multiple halogen substituents via selective metal–halogen exchange with lithium tri-n-butylmagnesium ate complex followed by trapping with di-t-butyl dicarbonate.

  吨丁基苯甲酸酯可以从通过选择性金属-卤素交换带有多个卤素取代基与锂三-芳族化合物可以访问正丁基镁根型配合物，接着用二-捕集叔丁基二碳酸酯。
• Closing the Cycle as It Begins: Synthesis of <i>ortho</i> ‐Iodobiaryls via Catellani Reaction
  作者：Vinayak Botla、Marco Fontana、Aleksandr Voronov、Raimondo Maggi、Elena Motti、Giovanni Maestri、Nicola Della Ca'

  DOI：10.1002/anie.202218928

  日期：——

  A new strategy based on the Catellani reactions has enabled the one-pot synthesis of ortho-iodobiaryls starting from aryl iodides and bromides. Beyond the synthetic utility of this transformation (32 examples and 6 subsequent derivatizations), a DFT study provides insights on the mechanism of the reductive elimination step, which is driven by an original transmetallation between palladium(II)-halide

  一种基于Catellani 反应的新策略使得能够从芳基碘化物和芳基溴化物开始一锅法合成邻碘二芳基化合物。除了这种转化的综合效用（32 个例子和 6 个后续衍生化）之外，DFT 研究还提供了对还原消除步骤机制的见解，该步骤由钯 (II)-卤化物络合物之间的原始金属转移作用驱动。
• Preparation of t-Butyl-3-Bromo-5-Formylbenzoate Through Selective Metal-Halogen Exchange Reactions
  作者：Arredondo, Juan D.、Li, Hongmei、Balsells, Jaume

  DOI：10.15227/orgsyn.089.0460

  日期：——
• PROCESS FOR PRODUCING PHENYLENE-CONTAINING POLYMER AND FILM-FORMING MATERIAL
  申请人：JSR Corporation

  公开号：EP0956312B1

  公开（公告）日：2001-10-10
• US6300465B1
  申请人：——

  公开号：US6300465B1

  公开（公告）日：2001-10-09