(4S,5R,6S)-2,4-Dimethyl-5-hydroxy-6-(p-methoxyphenyl)-1-hepten-3-one | 147879-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S,5R,6S)-2,4-Dimethyl-5-hydroxy-6-(p-methoxyphenyl)-1-hepten-3-one
• 英文别名: (4S,5R,6S)-5-hydroxy-6-(4-methoxyphenyl)-2,4-dimethylhept-1-en-3-one
• CAS: 147879-04-7
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: CAELVHMPHWAZOW-HWWQOWPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-2,4-Dimethyl-5-hydroxy-6-(p-methoxyphenyl)-1-hepten-3-one 在 sodium hydroxide 、 sodium tetrahydroborate 、 9-borabicyclo[3.3.1]nonane dimer 、 三乙基硼 、 双氧水 作用下， 反应 30.0h， 生成 (2S,3S,4S,5R,6S)-2,4-Dimethyl-6-(p-methoxyphenyl)-1,3,5-heptanetriol
  参考文献：
  名称：

  Efficient and highly stereoselective syntheses of enantiomerically enriched C(1)-C(7) subunits of erythronolides

  摘要：

  Stereocontrolled efficient syntheses of the C(1)-C(7) fragments of deoxyerythronolide and erythronolide seco acids are described. The key step of these syntheses involves a highly stereoselective aldol condensation between an enantiomerically enriched 2-arylpropanal and the lithium enolate of the racemic 2-methyl-5-norbornenyl ethyl ketone, which establishes in one operation the relative and absolute configurations of the three stereocenters C(2), C(3), and C(4). After syn-selective reductions of the carbonyl group, the configuration required at carbon C(6) was introduced by highly selective reactions carried out on the double bond regenerated by a thermal cycloreversion.

  DOI：

  10.1021/jo00063a009
• 作为产物：
  描述：

  (S)-2-(4-methoxyphenyl)propan-1-ol 在 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 二甲基亚砜 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， -50.0~500.0 ℃ 、1.33 Pa 条件下， 反应 8.25h， 生成 (4S,5R,6S)-2,4-Dimethyl-5-hydroxy-6-(p-methoxyphenyl)-1-hepten-3-one
  参考文献：
  名称：

  Efficient and highly stereoselective syntheses of enantiomerically enriched C(1)-C(7) subunits of erythronolides

  摘要：

  Stereocontrolled efficient syntheses of the C(1)-C(7) fragments of deoxyerythronolide and erythronolide seco acids are described. The key step of these syntheses involves a highly stereoselective aldol condensation between an enantiomerically enriched 2-arylpropanal and the lithium enolate of the racemic 2-methyl-5-norbornenyl ethyl ketone, which establishes in one operation the relative and absolute configurations of the three stereocenters C(2), C(3), and C(4). After syn-selective reductions of the carbonyl group, the configuration required at carbon C(6) was introduced by highly selective reactions carried out on the double bond regenerated by a thermal cycloreversion.

  DOI：

  10.1021/jo00063a009

文献信息

• Efficient and highly stereoselective syntheses of enantiomerically enriched C(1)-C(7) subunits of erythronolides
  作者：Mohammed Ahmar、Isabelle Romain、Robert Bloch

  DOI：10.1021/jo00063a009

  日期：1993.5

  Stereocontrolled efficient syntheses of the C(1)-C(7) fragments of deoxyerythronolide and erythronolide seco acids are described. The key step of these syntheses involves a highly stereoselective aldol condensation between an enantiomerically enriched 2-arylpropanal and the lithium enolate of the racemic 2-methyl-5-norbornenyl ethyl ketone, which establishes in one operation the relative and absolute configurations of the three stereocenters C(2), C(3), and C(4). After syn-selective reductions of the carbonyl group, the configuration required at carbon C(6) was introduced by highly selective reactions carried out on the double bond regenerated by a thermal cycloreversion.