2-bromo-1,3-ditosyl-1,3,2-diazaborolidine | 836637-10-6

• 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-bromo-1,3-ditosyl-1,3,2-diazaborolidine
• 英文别名: 1,3,2-Diazaborolidine, 2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-；2-bromo-1,3-bis-(4-methylphenyl)sulfonyl-1,3,2-diazaborolidine
• CAS: 836637-10-6
• 化学式: C₁₆H₁₈BBrN₂O₄S₂
• 分子量: 457.177
• InChiKey: GSMISULDXUGGEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-bromo-1,3-ditosyl-1,3,2-diazaborolidine 在 silver perchlorate 作用下， 以 硝基甲烷-d3 为溶剂， 生成
  参考文献：
  名称：

  The first N,N′-ditosyl-substituted cyclic boron cation, stabilized by neighboring-group participation by two sulfonyl groups, and the alternative, stabilized by polar solvents

  摘要：

  When 2-bromo-1,3-ditosyl-1,3,2-diazaborolidine was treated with AgSbF6, a novel cyclic boron cation was formed in CD2Cl2, the B-11 NMR chemical shift of which appeared at 8.7ppm. Ab initio calculations were consistent with the cationic boron center being stabilized by neighboring-group participation of the two sulfonyl functions. The reaction in CD3NO2, resulted in art alternate formation of a cyclic boron cation species (16.2ppm), stabilized by coordination to the basic solvents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.068
• 作为产物：
  描述：

  N,N-双(乙烯)-对甲苯磺酰胺 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-bromo-1,3-ditosyl-1,3,2-diazaborolidine
  参考文献：
  名称：

  The first N,N′-ditosyl-substituted cyclic boron cation, stabilized by neighboring-group participation by two sulfonyl groups, and the alternative, stabilized by polar solvents

  摘要：

  When 2-bromo-1,3-ditosyl-1,3,2-diazaborolidine was treated with AgSbF6, a novel cyclic boron cation was formed in CD2Cl2, the B-11 NMR chemical shift of which appeared at 8.7ppm. Ab initio calculations were consistent with the cationic boron center being stabilized by neighboring-group participation of the two sulfonyl functions. The reaction in CD3NO2, resulted in art alternate formation of a cyclic boron cation species (16.2ppm), stabilized by coordination to the basic solvents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.068

文献信息

• Asymmetric Total Syntheses of Hypoestin A, Albolic Acid, and Ceroplastol II
  作者：Yong-Qiang Wang、Kunhua Xu、Long Min、Chuang-Chuang Li

  DOI：10.1021/jacs.2c04633

  日期：2022.6.15

  hypoestin A, albolic acid, ceroplastol II, and schindilactone A, as well as other natural products, are efficiently and directly constructed via a unique intramolecular Pauson–Khand reaction of an allene-yne. This work represents the first reported use of the Pauson–Khand reaction to access synthetically challenging eight-membered-ring systems in natural product synthesis.

  具有史无前例的 [5-8-5-3] 四环骨架的生物活性二萜类hypoestin A 的第一个不对称全合成是从市售的 ( R )-柠檬烯分 15 步完成的。此外，还报道了 21 步中二酯萜类化合物 albolic acid 和 ceroplastol II 的第二次不对称全合成。具有综合挑战性和高度功能化的 [ X -8-5] ( X= 5 或 7) 在hypoestin A、albolic acid、ceroplastol II 和schindilactone A 以及其他天然产物中发现的三碳环系统是通过丙二烯-炔的独特分子内Pauson-Khand 反应有效和直接构建的。这项工作代表了首次报道使用 Pauson-Khand 反应在天然产物合成中获得具有综合挑战性的八元环系统。