1-(((4R,5R)-5-((4-methoxybenzyl)oxy)hept-1-en-4-yl)oxy)but-3-en-2-one | 1228459-72-0

• 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: 1-(((4R,5R)-5-((4-methoxybenzyl)oxy)hept-1-en-4-yl)oxy)but-3-en-2-one
• 英文别名: 1-[(4R,5R)-5-[(4-methoxyphenyl)methoxy]hept-1-en-4-yl]oxybut-3-en-2-one
• CAS: 1228459-72-0
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: XJXBPFVBZXROLA-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(((4R,5R)-5-((4-methoxybenzyl)oxy)hept-1-en-4-yl)oxy)but-3-en-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以86%的产率得到(R)-7-((R)-1-(4-methoxybenzyloxy)propyl)-6,7-dihydrooxepin-3(2H)-one
  参考文献：
  名称：

  Formal Total Syntheses of (+)-Prelaureatin and (+)-Laurallene by Diastereoselective Brook Rearrangement-Mediated [3 + 4] Annulation

  摘要：

  The formal syntheses of (+)-prelaureatin (1) and (+)-laurallene (2), halogenated eight-membered-ring ethers, are described. The key step of our strategy relies on diastereoselective construction of a trans-alpha,alpha'-disubstituted oxocene structure through a Brook rearrangement-mediated [3 + 4] annulation with acryloylsilane 9 and 6-oxa-2-cycloheptenone derivative 22'.

  DOI：

  10.1021/jo100708n
• 作为产物：
  描述：

  聚合甲醛 、 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以5.93 g的产率得到1-(((4R,5R)-5-((4-methoxybenzyl)oxy)hept-1-en-4-yl)oxy)but-3-en-2-one
  参考文献：
  名称：

  Formal Total Syntheses of (+)-Prelaureatin and (+)-Laurallene by Diastereoselective Brook Rearrangement-Mediated [3 + 4] Annulation

  摘要：

  The formal syntheses of (+)-prelaureatin (1) and (+)-laurallene (2), halogenated eight-membered-ring ethers, are described. The key step of our strategy relies on diastereoselective construction of a trans-alpha,alpha'-disubstituted oxocene structure through a Brook rearrangement-mediated [3 + 4] annulation with acryloylsilane 9 and 6-oxa-2-cycloheptenone derivative 22'.

  DOI：

  10.1021/jo100708n

文献信息

• Formal Total Syntheses of (+)-Prelaureatin and (+)-Laurallene by Diastereoselective Brook Rearrangement-Mediated [3 + 4] Annulation
  作者：Michiko Sasaki、Kazuhisa Oyamada、Kei Takeda

  DOI：10.1021/jo100708n

  日期：2010.6.4

  The formal syntheses of (+)-prelaureatin (1) and (+)-laurallene (2), halogenated eight-membered-ring ethers, are described. The key step of our strategy relies on diastereoselective construction of a trans-alpha,alpha'-disubstituted oxocene structure through a Brook rearrangement-mediated [3 + 4] annulation with acryloylsilane 9 and 6-oxa-2-cycloheptenone derivative 22'.