(2E,7E)-(4S,9S)-4,8-Dimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienoic acid ethyl ester | 594854-63-4

• 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: (2E,7E)-(4S,9S)-4,8-Dimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienoic acid ethyl ester
• CAS: 594854-63-4
• 化学式: C₂₂H₄₀O₄Si
• 分子量: 396.643
• InChiKey: CXXBNIYOEHVIPQ-BFSOOQBXSA-N

物化性质

• 沸点：
  450.9±45.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  27.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E,7E)-(4S,9S)-4,8-Dimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienoic acid ethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 potassium hexamethyldisilazane 、 二异丁基氢化铝 、 四乙基氟化铵水合物 、 lithium hexamethyldisilazane 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 (11E,16E)-(2R,5R,10S,15S,18R)-10-Ethyl-18-methoxy-11,15-dimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione
  参考文献：
  名称：

  Novel galbonolide derivatives as IPC synthase inhibitors: design, synthesis and in vitro antifungal activities

  摘要：

  A series of novel galbonolide derivatives having a modified methyl enol ether moiety were prepared in total synthetic procedures and evaluated for their in vitro antifungal activities. The antifungal activity was labile to modification of the enol ether functionality and almost all of the modified compounds lacked the activity except for the analogue with an introduction of a methylthio group at the C-6 position, which retained a modest antifungal potency against Cryptococcus neoformans. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.072
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 (E)-(2S,7S)-2,6-Dimethyl-4-methylene-7-(2-trimethylsilanyl-ethoxymethoxy)-non-5-enal 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以80%的产率得到(2E,7E)-(4S,9S)-4,8-Dimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienoic acid ethyl ester
  参考文献：
  名称：

  Novel galbonolide derivatives as IPC synthase inhibitors: design, synthesis and in vitro antifungal activities

  摘要：

  A series of novel galbonolide derivatives having a modified methyl enol ether moiety were prepared in total synthetic procedures and evaluated for their in vitro antifungal activities. The antifungal activity was labile to modification of the enol ether functionality and almost all of the modified compounds lacked the activity except for the analogue with an introduction of a methylthio group at the C-6 position, which retained a modest antifungal potency against Cryptococcus neoformans. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.072