(2E)-3-methyl-6-[(triethylsilyl)oxy]hex-2-en-1-ol | 1254375-53-5

• 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)-3-methyl-6-[(triethylsilyl)oxy]hex-2-en-1-ol
• 英文别名: (E)-3-methyl-6-((triethylsilyl)oxy)hex-2-en-1-ol；(E)-3-methyl-6-triethylsilyloxyhex-2-en-1-ol
• CAS: 1254375-53-5
• 化学式: C₁₃H₂₈O₂Si
• 分子量: 244.45
• InChiKey: PLXPDRNVFPDIBJ-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-3-methyl-6-[(triethylsilyl)oxy]hex-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 L-(+)-酒石酸二乙酯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 癸烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of air-stable nafuredin-γ analogs as complex I inhibitors

  摘要：

  Nafuredin-gamma (2), converted from nafuredin (1) under mild basic conditions, demonstrates potent and selective inhibitory activity against helminth complex I. However, 2 is unstable in air because the conjugated dienes are oxygen-labile. To address this, we designed and synthesized air-stable nafuredin-gamma analogs. Although the complex I inhibitory activities of all the new nafuredin-gamma analogs were lower than that of 2, all were in the high nM range (IC50: 300-820 nM). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.030
• 作为产物：
  描述：

  <(2E)-6-Hydroxy-3-methyl-2-hexenyl>acetat 在 咪唑 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 (2E)-3-methyl-6-[(triethylsilyl)oxy]hex-2-en-1-ol
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of air-stable nafuredin-γ analogs as complex I inhibitors

  摘要：

  Nafuredin-gamma (2), converted from nafuredin (1) under mild basic conditions, demonstrates potent and selective inhibitory activity against helminth complex I. However, 2 is unstable in air because the conjugated dienes are oxygen-labile. To address this, we designed and synthesized air-stable nafuredin-gamma analogs. Although the complex I inhibitory activities of all the new nafuredin-gamma analogs were lower than that of 2, all were in the high nM range (IC50: 300-820 nM). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.030

文献信息

• Synthesis of the C1-C14 Fragment of Sarcoglaucol-16-one via Z-Selective Ando-Type Horner-Wadsworth-Emmons Olefination
  作者：Sabine Laschat、Christoph Gastl

  DOI：10.1055/s-0029-1218825

  日期：2010.8

  A synthetic strategy involving a Z-selective Horner-Wadsworth-Emmons olefination was developed for the preparation of the sarcoglaucolone precursor methyl (2Z,6E)-8-(methoxymeth­oxy)-6-methyl-2-[(3E)-4-methyl-5-oxopent-3-enyl]-9-[(trimethylsilyl)methyl]deca-2,6,9-trienoate. The target compound was isolated in a E/Z ratio of 17:83

  开发了一种涉及Z选择性Horner-Wadsworth-Emmons烯烃化的合成策略，用于制备sarcoglaucolone前体——甲基(2Z,6E)-8-(甲氧基甲氧基)-6-甲基-2-[(3E)-4-甲基-5-氧戊-3-烯基]-9-[(三甲基硅基)甲基]癸-2,6,9-三烯酸酯。目标化合物以E/Z比率17:83被分离。
• Design, synthesis, and biological evaluation of air-stable nafuredin-γ analogs as complex I inhibitors
  作者：Masaki Ohtawa、Mari Matsunaga、Keiko Fukunaga、Risa Shimizu、Eri Shimizu、Shiho Arima、Junko Ohmori、Kiyoshi Kita、Kazuro Shiomi、Satoshi Omura、Tohru Nagamitsu

  DOI：10.1016/j.bmc.2015.01.030

  日期：2015.3

  Nafuredin-gamma (2), converted from nafuredin (1) under mild basic conditions, demonstrates potent and selective inhibitory activity against helminth complex I. However, 2 is unstable in air because the conjugated dienes are oxygen-labile. To address this, we designed and synthesized air-stable nafuredin-gamma analogs. Although the complex I inhibitory activities of all the new nafuredin-gamma analogs were lower than that of 2, all were in the high nM range (IC50: 300-820 nM). (C) 2015 Elsevier Ltd. All rights reserved.