methyl 2-[(1R,4R,5S,7R)-4-hydroxy-5,7-dimethyl-6-oxocyclohept-2-en-1-yl]acetate | 401911-96-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-[(1R,4R,5S,7R)-4-hydroxy-5,7-dimethyl-6-oxocyclohept-2-en-1-yl]acetate
• CAS: 401911-96-4
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: QFLPFTFLZQRGLN-XFWSIPNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-[(1R,4R,5S,7R)-4-hydroxy-5,7-dimethyl-6-oxocyclohept-2-en-1-yl]acetate 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (3aS,4R,5R,6R,7R,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-4,6-dimethyl-octahydro-cyclohepta[b]furan-2-one
  参考文献：
  名称：

  Oxabicyclo[3.2.1]octenes in Organic SynthesisDirect Ring Opening of Oxabicyclo[3.2.1] Systems Employing Silyl Ketene Acetals in Concentrated Solutions of Lithium Perchlorate−Diethyl Ether:  Application to the Synthesis of the C(19)−C(27) Fragment of Rifamycin S

  摘要：

  [GRAPHICS]The direct opening at the bridgehead of oxabicyclo[3.2.1]octenes employing silyl ketene acetals in 4.0-5.0 M lithium perchlorate in diethyl ether has been realized, which gives rise to highly functionalized cycloheptadienes that can be further manipulated for use in natural product synthesis. The bridgehead opening reaction has been employed in the construction of the C(19)-C(27) fragment of Rifamycin S.

  DOI：

  10.1021/ol0003836
• 作为产物：
  描述：

  tert-butyl-[[(1S,4S,5R)-2,4-dimethyl-8-oxabicyclo[3.2.1]octa-2,6-dien-3-yl]oxy]-dimethylsilane 在 四丁基氟化铵 、 lithium perchlorate 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 为溶剂， 反应 60.0h， 生成 methyl 2-[(1R,4R,5S,7R)-4-hydroxy-5,7-dimethyl-6-oxocyclohept-2-en-1-yl]acetate
  参考文献：
  名称：

  Oxabicyclo[3.2.1]octenes in Organic SynthesisDirect Ring Opening of Oxabicyclo[3.2.1] Systems Employing Silyl Ketene Acetals in Concentrated Solutions of Lithium Perchlorate−Diethyl Ether:  Application to the Synthesis of the C(19)−C(27) Fragment of Rifamycin S

  摘要：

  [GRAPHICS]The direct opening at the bridgehead of oxabicyclo[3.2.1]octenes employing silyl ketene acetals in 4.0-5.0 M lithium perchlorate in diethyl ether has been realized, which gives rise to highly functionalized cycloheptadienes that can be further manipulated for use in natural product synthesis. The bridgehead opening reaction has been employed in the construction of the C(19)-C(27) fragment of Rifamycin S.

  DOI：

  10.1021/ol0003836

文献信息

• Oxabicyclo[3.2.1]octenes in Organic Synthesis:  Direct Ring Opening of Oxabicyclo[3.2.1] Ring Systems with Diisobutylaluminum Hydride and a Silyl Ketene AcetalSynthesis of the Chiral C(19)−C(26) and C(27)−C(32) Fragments of Scytophycin C
  作者：Kevin W. Hunt、Paul A. Grieco

  DOI：10.1021/ol010253c

  日期：2002.1.1

  GRAPHICSAn efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.
• Oxabicyclo[3.2.1]octenes in Organic SynthesisDirect Ring Opening of Oxabicyclo[3.2.1] Systems Employing Silyl Ketene Acetals in Concentrated Solutions of Lithium Perchlorate−Diethyl Ether:  Application to the Synthesis of the C(19)−C(27) Fragment of Rifamycin S
  作者：Kevin W. Hunt、Paul A. Grieco

  DOI：10.1021/ol0003836

  日期：2001.2.1

  [GRAPHICS]The direct opening at the bridgehead of oxabicyclo[3.2.1]octenes employing silyl ketene acetals in 4.0-5.0 M lithium perchlorate in diethyl ether has been realized, which gives rise to highly functionalized cycloheptadienes that can be further manipulated for use in natural product synthesis. The bridgehead opening reaction has been employed in the construction of the C(19)-C(27) fragment of Rifamycin S.