(E)-(4S,9S)-3-Hydroxy-4,8-dimethyl-6-methylene-2-(2,2,2-trifluoro-ethoxy)-9-(2-trimethylsilanyl-ethoxymethoxy)-undec-7-enoic acid methyl ester | 594854-81-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (E)-(4S,9S)-3-Hydroxy-4,8-dimethyl-6-methylene-2-(2,2,2-trifluoro-ethoxy)-9-(2-trimethylsilanyl-ethoxymethoxy)-undec-7-enoic acid methyl ester
• CAS: 594854-81-6
• 化学式: C₂₃H₄₁F₃O₆Si
• 分子量: 498.656
• InChiKey: WFESBASOLKZNAI-RYQMCNPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-(4S,9S)-3-Hydroxy-4,8-dimethyl-6-methylene-2-(2,2,2-trifluoro-ethoxy)-9-(2-trimethylsilanyl-ethoxymethoxy)-undec-7-enoic acid methyl ester 在 咪唑 、 碘 、 二异丁基氢化铝 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 作用下， 生成 {2-[(2E,7Z)-(1S,6S)-1-Ethyl-9-iodo-2,6-dimethyl-4-methylene-8-(2,2,2-trifluoro-ethoxy)-nona-2,7-dienyloxymethoxy]-ethyl}-trimethyl-silane
  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：

  (E)-(2S,7S)-2,6-Dimethyl-4-methylene-7-(2-trimethylsilanyl-ethoxymethoxy)-non-5-enal 、 2-(2,2,2-三氟乙氧基)乙酸甲酯 在 lithium hexamethyldisilazane 作用下， 生成 (E)-(4S,9S)-3-Hydroxy-4,8-dimethyl-6-methylene-2-(2,2,2-trifluoro-ethoxy)-9-(2-trimethylsilanyl-ethoxymethoxy)-undec-7-enoic acid methyl 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