Butanoic acid, 2-[(4-methoxyphenyl)methoxy]-4-(phenylseleno)-, methylester, (2R)- | 364337-18-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Butanoic acid, 2-[(4-methoxyphenyl)methoxy]-4-(phenylseleno)-, methylester, (2R)-
• 英文别名: methyl (2R)-2-p-methoxybenzyloxy-4-phenylselanylbutanoate；methyl (2R)-2-p-methoxybenzyloxy-4-phenylselenylbutanoate
• CAS: 364337-18-8
• 化学式: C₁₉H₂₂O₄Se
• 分子量: 393.341
• InChiKey: ZIRYISMLCUOFSU-GOSISDBHSA-N

物化性质

• 沸点：
  493.1±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  Butanoic acid, 2-[(4-methoxyphenyl)methoxy]-4-(phenylseleno)-, methylester, (2R)- 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 copper(l) iodide 、 三甲基铝 、 二异丁基氢化铝 、 四丁基高碘酸铵 、 silver(l) oxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 氯仿 、 甲苯 为溶剂， 反应 51.08h， 生成 (2S,3S,4R,5S)-2-((E)-1,5-dimethylhex-1-enyl)-3-methoxy-4-p-methoxybenzyloxy-5-methylcyclohexanone
  参考文献：
  名称：

  MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

  摘要：

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

  DOI：

  10.1021/jo035065+
• 作为产物：
  描述：

  在 camphor-10-sulfonic acid 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 Butanoic acid, 2-[(4-methoxyphenyl)methoxy]-4-(phenylseleno)-, methylester, (2R)-
  参考文献：
  名称：

  MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

  摘要：

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

  DOI：

  10.1021/jo035065+

文献信息

• A New, Ring Closing Metathesis-Based Synthesis of (−)-Fumagillol
  作者：Jean-Guy Boiteau、Pierre Van de Weghe、Jacques Eustache

  DOI：10.1021/ol016343z

  日期：2001.8.1

  [GRAPHICS]A new strategy to access the fumagillin/fumagillol skeleton is proposed. An Evans aldolization and a RCM involving an enone are used for the preparation of a key cyclohexanone intermediate, which was readily converted to fumagillol. The synthesis also features an efficient preparation of isogeraniol and isogeranic acid.