(E)-2-(trimethylsilylmethyl)hept-2-enoyl chloride | 405297-75-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (E)-2-(trimethylsilylmethyl)hept-2-enoyl chloride
• CAS: 405297-75-8
• 化学式: C₁₁H₂₁ClOSi
• 分子量: 232.826
• InChiKey: PBZLNKWODMNIKZ-CSKARUKUSA-N

物化性质

• 沸点：
  273.2±23.0 °C(predicted)
• 密度：
  0.939±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  14
• 可旋转键数：
  6
• 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：

  (E)-2-(trimethylsilylmethyl)hept-2-enoyl chloride 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  三组分曼尼希反应的合成应用。IL-6抑制剂（+）-madindoline A和B的全合成

  摘要：

  3a-羟基呋喃二氢吲哚（3），β-​​酮酸酯和甲醛的三组分曼尼希反应被用作合成天然存在的（+）-Madindolines A（1）和B（2）的有效而简洁的方法。描述了曼尼希反应与3的范围和局限性。

  DOI：

  10.1016/j.tetlet.2006.07.083
• 作为产物：
  描述：

  2-trimethylsilylmethyl-2-heptenoic acid 在 氯化亚砜 作用下， 反应 4.0h， 以100%的产率得到(E)-2-(trimethylsilylmethyl)hept-2-enoyl 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.
• Synthetic applications of a three-component Mannich reaction. Total synthesis of IL-6 inhibitor (+)-madindoline A and B
  作者：Tomoyasu Hirose、Toshiaki Sunazuka、Daisuke Yamamoto、Eisuke Kaji、Satoshi Ōmura

  DOI：10.1016/j.tetlet.2006.07.083

  日期：2006.9

  A three-component Mannich reaction of 3a-hydroxyfuroindoline (3), β-ketoester and formaldehyde was employed as an efficient and concise method to synthesize naturally-occurring (+)-Madindolines A (1) and B (2). The scope and limitations of the Mannich reaction with 3 are described.

  3a-羟基呋喃二氢吲哚（3），β-​​酮酸酯和甲醛的三组分曼尼希反应被用作合成天然存在的（+）-Madindolines A（1）和B（2）的有效而简洁的方法。描述了曼尼希反应与3的范围和局限性。