(S,E)-8-(benzyloxymethoxy)tetradec-4-ene-3,9-dione | 1618091-81-8

• 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: (S,E)-8-(benzyloxymethoxy)tetradec-4-ene-3,9-dione
• 英文别名: (E,8S)-8-(phenylmethoxymethoxy)tetradec-4-ene-3,9-dione
• CAS: 1618091-81-8
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: RCFMFEUFWONMES-GWECRGSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,E)-8-(benzyloxymethoxy)tetradec-4-ene-3,9-dione 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 74.0h， 生成 1-((2R,5S,6R)-5-(benzyloxymethoxy)-6-pentyltetrahydro-2H-pyran-2-yl)butan-2-one
  参考文献：
  名称：

  Selective Transformations of Carbonyl Functions in the Presence of α,β-Unsaturated Ketones: Concise Asymmetric Total Synthesis of Decytospolides A and B

  摘要：

  Enones selectively react with a combination of PPh3 and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.

  DOI：

  10.1021/ol501463p
• 作为产物：
  描述：

  2-戊基-2-环戊烯-1-酮 在 C₁₁H₂₂BNO 、 dimethyl sulfide borane 、 臭氧 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.67h， 生成 (S,E)-8-(benzyloxymethoxy)tetradec-4-ene-3,9-dione
  参考文献：
  名称：

  Selective Transformations of Carbonyl Functions in the Presence of α,β-Unsaturated Ketones: Concise Asymmetric Total Synthesis of Decytospolides A and B

  摘要：

  Enones selectively react with a combination of PPh3 and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.

  DOI：

  10.1021/ol501463p

文献信息

• Selective Transformations of Carbonyl Functions in the Presence of α,β-Unsaturated Ketones: Concise Asymmetric Total Synthesis of Decytospolides A and B
  作者：Kenzo Yahata、Masaki Minami、Kei Watanabe、Hiromichi Fujioka

  DOI：10.1021/ol501463p

  日期：2014.7.18

  Enones selectively react with a combination of PPh3 and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.