(2R)-2-p-methoxybenzyloxy-4-phenylselanylbutanal | 364337-19-9

• 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: (2R)-2-p-methoxybenzyloxy-4-phenylselanylbutanal
• 英文别名: (2R)-2-p-methoxybenzyloxy-4-phenylselenylbutanal；Butanal, 2-[(4-methoxyphenyl)methoxy]-4-(phenylseleno)-, (2R)-；(2R)-2-[(4-methoxyphenyl)methoxy]-4-phenylselanylbutanal
• CAS: 364337-19-9
• 化学式: C₁₈H₂₀O₃Se
• 分子量: 363.315
• InChiKey: FXMOJXHQWKILND-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-p-methoxybenzyloxy-4-phenylselanylbutanal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三丁基膦 、 三甲基铝 、 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 、 水 、 甲苯 为溶剂， 反应 64.75h， 生成 (4R,5S,6S)-6-[(E)-1,5-dimethylhex-1-enyl]-2-hydroxymethyl-5-methoxy-4-p-methoxybenzyloxycyclohex-2-enone
  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：

  Butanoic acid, 2-[(4-methoxyphenyl)methoxy]-4-(phenylseleno)-, methylester, (2R)- 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以94%的产率得到(2R)-2-p-methoxybenzyloxy-4-phenylselanylbutanal
  参考文献：
  名称：

  A New, Ring Closing Metathesis-Based Synthesis of (−)-Fumagillol

  摘要：

  [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.

  DOI：

  10.1021/ol016343z

文献信息

• MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues
  作者：Vincent Rodeschini、Jean-Guy Boiteau、Pierre Van de Weghe、Céline Tarnus、Jacques Eustache

  DOI：10.1021/jo035065+

  日期：2004.1.1

  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.
• 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.