(E)-2-hydroxy-3,5-dichloro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene | 1333375-03-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-hydroxy-3,5-dichloro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene
• 英文别名: 2-hydroxy-3,5-dichloro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene；2,4-dichloro-6-{2-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-phenyl]-vinyl}-phenol；2,4-dichloro-6-[(E)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethenyl]phenol
• CAS: 1333375-03-3
• 化学式: C₂₀H₂₁BCl₂O₃
• 分子量: 391.102
• InChiKey: FLTPMCLWNXKCHF-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲基苯硼酸频哪醇酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium t-butanolate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 (E)-2-hydroxy-3,5-dichloro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene 、 (E)-2-hydroxy-3,5-dichloro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene
  参考文献：
  名称：

  Synthesis of Pinacolylboronate-Substituted Stilbenes and their application to the synthesis of boron capped polyenes

  摘要：

  A series of novel 4,4,5,5-tetramethyl-2-(4-substitutedstyrylphenyl)-1,3,2 dioxaborolane derivatives has been synthesized. 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide (4) was treated with 3 equiv of tBuONa, various aldehydes in the presence of DMF, and stirred at room temperature 4-6 h to yield the corresponding boron containing stilbene derivatives 1 a-n in 71 -94% yields. A one-pot protocol transformation has also been developed and used this methodology to synthesize boron containing resveratrol analogues. Simple and clean reactions, high yield of the products are the salient features of this methodology. We used this reaction to synthesize the boron capped polyenes. These boron containing polyene systems are potential intermediate to synthesize conjugated polyene as new material for LCD (Liquid Crystal Display) technology. The biological testing of these compounds is currently underway to identify potential therapeutic for Neurodegenerative diseases. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.08.007

文献信息

• Design and synthesis of novel pinacolylboronate containing combretastatin ‘antimitotic agent’ analogues
  作者：Bhaskar C. Das、Sakkarapalayam M. Mahalingam、Todd Evans

  DOI：10.1016/j.tetlet.2009.04.003

  日期：2009.6

  We developed a procedure to synthesize pinacolyl boronate containing stilbene derivatives and used this procedure to synthesize boron-containing combretastatin analogues. The key step involves the Wittig reaction of the ylide 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 11 with 3,4,5-trimethoxy benzaldehyde in the presence of (1)BuONa in DMF, providing 88% yield. We are now in a position to evaluate the biological activity of these derivatives as modulators of TGF-beta signaling pathways. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Pinacolylboronate-Substituted Stilbenes and their application to the synthesis of boron capped polyenes
  作者：Bhaskar C. Das、Sakkarapalayam M. Mahalingam、Sasmita Das、Narayan S. Hosmane、Todd Evans

  DOI：10.1016/j.jorganchem.2015.08.007

  日期：2015.12

  A series of novel 4,4,5,5-tetramethyl-2-(4-substitutedstyrylphenyl)-1,3,2 dioxaborolane derivatives has been synthesized. 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide (4) was treated with 3 equiv of tBuONa, various aldehydes in the presence of DMF, and stirred at room temperature 4-6 h to yield the corresponding boron containing stilbene derivatives 1 a-n in 71 -94% yields. A one-pot protocol transformation has also been developed and used this methodology to synthesize boron containing resveratrol analogues. Simple and clean reactions, high yield of the products are the salient features of this methodology. We used this reaction to synthesize the boron capped polyenes. These boron containing polyene systems are potential intermediate to synthesize conjugated polyene as new material for LCD (Liquid Crystal Display) technology. The biological testing of these compounds is currently underway to identify potential therapeutic for Neurodegenerative diseases. (C) 2015 Elsevier B.V. All rights reserved.