[(1R,4R,5R,6R,7R)-6-hydroxy-4-(2-methoxy-2-oxoethyl)-5,7-dimethylcyclohept-2-en-1-yl] (2S)-2-methoxy-2-phenylacetate | 401911-98-6

• 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: [(1R,4R,5R,6R,7R)-6-hydroxy-4-(2-methoxy-2-oxoethyl)-5,7-dimethylcyclohept-2-en-1-yl] (2S)-2-methoxy-2-phenylacetate
• CAS: 401911-98-6
• 化学式: C₂₁H₂₈O₆
• 分子量: 376.45
• InChiKey: IWYNZBDXFHDJGR-UQHXUKELSA-N

物化性质

• 沸点：
  483.3±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1R,4R,5R,6R,7R)-6-hydroxy-4-(2-methoxy-2-oxoethyl)-5,7-dimethylcyclohept-2-en-1-yl] (2S)-2-methoxy-2-phenylacetate 在 三(三甲基硅基)硅烷 、 saponification reagent 、 苯甲酸酐 作用下， 以 甲苯 为溶剂， 生成 (3aS,4R,5S,6S,8aR)-5-hydroxy-4,6-dimethyl-3,3a,4,5,6,8a-hexahydrocyclohepta[b]furan-2-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/ol010253c
• 作为产物：
  描述：

  无 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 [(1R,4R,5R,6R,7R)-6-hydroxy-4-(2-methoxy-2-oxoethyl)-5,7-dimethylcyclohept-2-en-1-yl] (2S)-2-methoxy-2-phenylacetate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/ol010253c

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.