(R)-7-((R)-1-(4-methoxybenzyloxy)propyl)-6,7-dihydrooxepin-3(2H)-one | 1228459-59-3

• 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: (R)-7-((R)-1-(4-methoxybenzyloxy)propyl)-6,7-dihydrooxepin-3(2H)-one
• 英文别名: (2R)-2-[(1R)-1-[(4-methoxyphenyl)methoxy]propyl]-2,3-dihydrooxepin-6-one
• CAS: 1228459-59-3
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: NVUYZPUJUAQEOX-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-[tert-butyl(dimethyl)silyl]-3-[dimethyl(phenyl)silyl]prop-2-en-1-one 、 (R)-7-((R)-1-(4-methoxybenzyloxy)propyl)-6,7-dihydrooxepin-3(2H)-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.96h， 以80%的产率得到(1R,3R,5R,6S)-8-(tert-butyldimethylsilyloxy)-6-(dimethyl(phenyl)silyl)-3-((R)-1-(4-methoxybenzyloxy)propyl)-2-oxabicyclo[3.3.2]-dec-7-en-9-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：

  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

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'.