(2E)-2-ethylidene-3-trimethylsilylhexanoyl chloride | 405297-77-0

• 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: (2E)-2-ethylidene-3-trimethylsilylhexanoyl chloride
• CAS: 405297-77-0
• 化学式: C₁₁H₂₁ClOSi
• 分子量: 232.826
• InChiKey: XQIVQZYVHREMRF-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-2-ethylidene-3-trimethylsilylhexanoyl chloride 在 N-碘代丁二酰亚胺 、 四丁基二氟三苯硅酸铵 作用下， 以 二氯甲烷 为溶剂， 生成 (2R)-2-[[(3aS,8bR)-8b-hydroxy-7-iodo-2,3a-dihydro-1H-furo[2,3-b]indol-4-yl]methyl]-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione
  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：

  2-ethylidene-3-trimethylsilylhexanoic acid 在 氯化亚砜 作用下， 反应 4.0h， 以100%的产率得到(2E)-2-ethylidene-3-trimethylsilylhexanoyl chloride
  参考文献：
  名称：

  Short Total Synthesis of (+)-Madindolines A and B

  摘要：

  A short and efficient total synthesis of (+)-madindolines A (1) and B (2), potent and selective inhibitors of interleukin 6, has been achieved. The synthesis features a key chelation-controlled 1,4-diastereoselective acylation to generate the quaternary carbon and an intramolecular acylation of allylsilane to build up the cyclopentene unit.

  DOI：

  10.1021/ol017058i

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.
• Short Total Synthesis of (+)-Madindolines A and B
  作者：Tomoyasu Hirose、Toshiaki Sunazuka、Tatsuya Shirahata、Daisuke Yamamoto、Yoshihiro Harigaya、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1021/ol017058i

  日期：2002.2.1

  A short and efficient total synthesis of (+)-madindolines A (1) and B (2), potent and selective inhibitors of interleukin 6, has been achieved. The synthesis features a key chelation-controlled 1,4-diastereoselective acylation to generate the quaternary carbon and an intramolecular acylation of allylsilane to build up the cyclopentene unit.