trimethylsilyl (E)-4-bromopent-2-enoate | 88239-40-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: trimethylsilyl (E)-4-bromopent-2-enoate
• CAS: 88239-40-1
• 化学式: C₈H₁₅BrO₂Si
• 分子量: 251.195
• InChiKey: FMMIDARAQRIRRB-AATRIKPKSA-N

物化性质

• 沸点：
  108 °C(Press: 10 Torr)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trimethylsilyl (E)-4-bromopent-2-enoate 在 水 作用下， 反应 0.08h， 生成 (E)-4-Bromo-2-pentenoic Acid
  参考文献：
  名称：

  Silicon in Organic Synthesis: An Improved 4-Bromination of 2-Alkenoic Acids

  摘要：

  DOI：

  10.1055/s-1983-30497
• 作为产物：
  描述：

  反式-2-戊烯酸 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 6.25h， 生成 trimethylsilyl (E)-4-bromopent-2-enoate
  参考文献：
  名称：

  Silicon in Organic Synthesis: An Improved 4-Bromination of 2-Alkenoic Acids

  摘要：

  DOI：

  10.1055/s-1983-30497

文献信息

• Synthesis and Structure−Activity Relationships of 6,7-Disubstituted 4-Anilinoquinoline-3-carbonitriles. The Design of an Orally Active, Irreversible Inhibitor of the Tyrosine Kinase Activity of the Epidermal Growth Factor Receptor (EGFR) and the Human Epidermal Growth Factor Receptor-2 (HER-2)
  作者：Allan Wissner、Elsebe Overbeek、Marvin F. Reich、M. Brawner Floyd、Bernard D. Johnson、Nellie Mamuya、Edward C. Rosfjord、Carolyn Discafani、Rachel Davis、Xiaoqing Shi、Sridhar K. Rabindran、Brian C. Gruber、Fei Ye、William A. Hallett、Ramaswamy Nilakantan、Ru Shen、Yu-Fen Wang、Lee M. Greenberger、Hwei-Ru Tsou

  DOI：10.1021/jm020241c

  日期：2003.1.1

  A series of of 6,7-disubstituted-4-anilinoquinoline-3-carbonitrile derivatives that function as irreversible inhibitors of EGFR and HER-2 kinases have been prepared. These inhibitors have, at the 6-position, butynamide, crotonamide, and methacrylamide Michael acceptors bearing water-solublilizing substituents. These compounds were prepared by acylation of 6-amino-4-(arylamino)quinoline-3-carbonitriles with unsaturated acid chlorides or mixed anhydrides. We performed competitive reactivity studies showing that attaching a dialkylamino group onto the end of the Michael acceptor results in compounds with greater reactivity due to intramolecular catalysis of the Michael addition. This, along with improved water-solubility results in compounds with enhanced biological properties. We present molecular modeling results consistent with the proposed mechanism of inhibition. One compound, 5 (EKB-569), which shows excellent oral in vivo activity, was selected for further studies and is currently in phase I clinical trials for the treatment of cancer.
• BELLASSOUED, M.;HABBACHI, F.;GAUDEMAR, M., SYNTHESIS, BRD, 1983, N 9, 745-746
  作者：BELLASSOUED, M.、HABBACHI, F.、GAUDEMAR, M.

  DOI：——

  日期：——
• Silicon in Organic Synthesis: An Improved 4-Bromination of 2-Alkenoic Acids
  作者：M. Bellassoued、F. Habbachi、M. Gaudemar

  DOI：10.1055/s-1983-30497

  日期：——