4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane | 1169942-88-4

• 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: 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-[4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]-1,3,2-dioxaborolane
• CAS: 1169942-88-4
• 化学式: C₂₃H₂₉BO₅
• 分子量: 396.291
• InChiKey: HXOSLTZJNRWYOR-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4-甲基苯基硼酸频哪醇酯)三苯基溴化膦 、 3,4,5-三甲氧基苯甲醛 在 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane 、 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane
  参考文献：
  名称：

  Design and synthesis of novel pinacolylboronate containing combretastatin ‘antimitotic agent’ analogues

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.04.003

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.