(E)-2-Trimethylsilanylmethyl-pent-2-enoic acid | 888020-94-8

• 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: (E)-2-Trimethylsilanylmethyl-pent-2-enoic acid
• CAS: 888020-94-8
• 化学式: C₉H₁₈O₂Si
• 分子量: 186.326
• InChiKey: LHSMPLQOLXQKBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-2-Trimethylsilanylmethyl-pent-2-enoic acid 在 氯化亚砜 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-(S)-2-[(3aR,8aS)-3a-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-2-methyl-3-oxo-4-trimethylsilanylmethyl-hept-4-enoic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and biological activities of madindoline analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.01.107
• 作为产物：
  描述：

  在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以99%的产率得到(E)-2-Trimethylsilanylmethyl-pent-2-enoic acid
  参考文献：
  名称：

  Design, synthesis, and biological activities of madindoline analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.01.107

文献信息

• Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis
  作者：Selin E. Donmez、Emine Soydaş、Gökçen Aydın、Onur Şahin、Uğur Bozkaya、Yunus E. Türkmen

  DOI：10.1021/acs.orglett.8b03886

  日期：2019.1.18

  α-methylene-γ-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80 °C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the −TMS group in reducing the reaction barrier of the key cyclization step.

  已开发出3,4-二氢异喹啉与α，β-不饱和酰氯之间的催化氮杂-Nazarov环化反应，以高收率（高达79％）作为单一非对映异构体获得α-亚甲基-γ-内酰胺产品。当AgOTf用作阴离子交换催化剂时，在80°C下负载量为20 mol％时，反应有效进行。进行了计算研究以研究反应机理，并且该发现支持-TMS基团在减少关键环化步骤的反应障碍中的作用。