(3R,4S,5R,6S)-2,4-Dimethyl-6-(p-methoxyphenyl)-1-heptene-3,5-diol | 148215-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3R,4S,5R,6S)-2,4-Dimethyl-6-(p-methoxyphenyl)-1-heptene-3,5-diol
• 英文别名: (3R,4S,5R,6S)-6-(4-Methoxyphenyl)-2,4-dimethyl-1-heptene-3,5-diol；(3R,4S,5R,6S)-6-(4-methoxyphenyl)-2,4-dimethylhept-1-ene-3,5-diol
• CAS: 148215-93-4
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: SBGIKFWMBKTGJV-SHUKQUCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6S)-2,4-Dimethyl-6-(p-methoxyphenyl)-1-heptene-3,5-diol 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 作用下， 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 、 sodium tetrahydroborate 、 正丁基锂 、 三乙基硼 、 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， -70.0~500.0 ℃ 、1.33 Pa 条件下， 反应 13.25h， 生成 (3R,4S,5R,6S)-2,4-Dimethyl-6-(p-methoxyphenyl)-1-heptene-3,5-diol
  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.