ethyl 2-<(trimethylsilyl)methyl>-2-butenoate | 80361-24-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-<(trimethylsilyl)methyl>-2-butenoate
• 英文别名: Ethyl 2-(trimethylsilylmethyl)but-2-enoate
• CAS: 80361-24-6
• 化学式: C₁₀H₂₀O₂Si
• 分子量: 200.353
• InChiKey: AMUWMDXQSBJJLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  ethyl 2-<(trimethylsilyl)methyl>-2-butenoate 在 草酰氯 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 4-<(trimethylsilyl)methyl>-2,4-hexadien-1-ol
  参考文献：
  名称：

  Synthesis of the cytochalasin D isoindolone unit: solutions to the problem of regiochemistry in N-benzoylpyrrolinone Diels-Alder reactions

  摘要：

  DOI：

  10.1021/jo00347a034
• 作为产物：
  描述：

  乙基3-(三甲基硅基)丙酸酯 在 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium diisopropyl amide 作用下， 反应 33.0h， 生成 ethyl 2-<(trimethylsilyl)methyl>-2-butenoate
  参考文献：
  名称：

  Synthesis of the cytochalasin D isoindolone unit: solutions to the problem of regiochemistry in N-benzoylpyrrolinone Diels-Alder reactions

  摘要：

  DOI：

  10.1021/jo00347a034

文献信息

• Design, synthesis, and biological activities of madindoline analogues
  作者：Daisuke Yamamoto、Toshiaki Sunazuka、Tomoyasu Hirose、Naoto Kojima、Eisuke Kaji、Satoshi Omura

  DOI：10.1016/j.bmcl.2006.01.107

  日期：2006.5

  A research program is under way to develop a series of madindoline-based inhibitors targeting interleukin 6. Such inhibitors will have potential use in fighting a variety of diseases for which no effective therapeutic drugs currently exist. Madindoline is no longer available from natural Sources. Consequently, we have developed a purely synthetic route to ensure a supply of the compound. The synthesis of a range of analogues is described, all of which were evaluated for their inhibitory activity against the growth of IL-6-dependent 7TDI cells. From these assays, several synthetic madindoline analogues were identified as highly promising candidates for further development. (C) 2006 Published by Elsevier Ltd.
• A novel approach to complex terpenoid methylenecyclohexanes
  作者：Rolf Henning、H.M.R. Hoffman

  DOI：10.1016/s0040-4039(00)87327-x

  日期：1982.1
• Amination of α,β-unsaturated (2-trimethylsilanylmethyl) carboxylic esters
  作者：Tecla Gasperi、M Antonietta Loreto、Paolo A Tardella、Augusto Gambacorta

  DOI：10.1016/s0040-4039(02)00390-8

  日期：2002.4

  The reactions of (2-trimethylsilanylmethyl) alpha,beta-unsaturated carboxylic ethyl esters with NsONHCO(2)Et and CaO produce, after treatment with AcOH, alpha-methylene N-(ethoxycarbonyl) beta-amino carboxylic esters through ring opening and elimination of the trimethylsilyl group from the intermediate aziridine. By ozonization and subsequent reductive cleavage these products give the corresponding N-(ethoxycarbonyl) beta-amino alpha-hydroxy esters. (C) 2002 Elsevier Science Ltd. All rights reserved.