3-(2,4-Dimethoxyphenyl)-3-phenylallylalkohol | 10386-54-6

• 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: 3-(2,4-Dimethoxyphenyl)-3-phenylallylalkohol
• 英文别名: (Z)-3-(2,4-dimethoxyphenyl)-3-phenylprop-2-en-1-ol
• CAS: 10386-54-6
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: JHJUQPCJLGABKU-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,4-Dimethoxyphenyl)-3-phenylallylalkohol 在 [Rh((R,R)-bdpp)(NBD)]ClO₄ sodium periodate 、 三丁基膦 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 170.0h， 生成 (S)-3-(2',4'-dimethoxyphenyl)-3-phenyl-1-propene
  参考文献：
  名称：

  Stereoselective Synthesis of (R)- and (S)-4-Methoxydalbergione via Asymmetric Catalytic Hydrogenation

  摘要：

  [GRAPHICS](R)-(+)- and (S)-(-)-4-methoxydalbergione were synthesized in seven steps with an enantiomeric excess of up to 95% using an asymmetric catalytic hydrogenation step with [Rh((S,S)-bdpp)(NBD)]ClO4 or [Rh((R,R)-bdpp)(NBD)]ClO4, respectively, at a hydrogen pressure of 80 bar. This method should give an easy access to the other members of the dalbergione family.

  DOI：

  10.1021/ol990961m
• 作为产物：
  描述：

  7-甲氧基-4-苯基色烯-2-酮 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 生成 3-(2,4-Dimethoxyphenyl)-3-phenylallylalkohol
  参考文献：
  名称：

  Stereoselective Synthesis of (R)- and (S)-4-Methoxydalbergione via Asymmetric Catalytic Hydrogenation

  摘要：

  [GRAPHICS](R)-(+)- and (S)-(-)-4-methoxydalbergione were synthesized in seven steps with an enantiomeric excess of up to 95% using an asymmetric catalytic hydrogenation step with [Rh((S,S)-bdpp)(NBD)]ClO4 or [Rh((R,R)-bdpp)(NBD)]ClO4, respectively, at a hydrogen pressure of 80 bar. This method should give an easy access to the other members of the dalbergione family.

  DOI：

  10.1021/ol990961m

文献信息

• Approach to the stereoselective synthesis of (R)- and (S)-4-methoxydalbergione via asymmetric catalytic hydrogenation
  作者：Philippe Bissel、Rafaël Sablong、Jean-Pierre Lepoittevin

  DOI：10.1016/0957-4166(95)00082-z

  日期：1995.4

  the synthesis of 4-methoxybalbergione, was prepared from compound 6 with an enantiomeric excess of 17 to 94% by asymmetric catalytic hydrogenation using rhodium or ruthenium chiral complexes. The best hydrogenation results were obtained using [Rh((S,S)-bdpp)(NBD)] ClO4, and [Rh((R,R)-bdpp)(NBD)] ClO4, at a hydrogen pressure of 80 bar.

  通过使用铑或钌手性配合物的不对称催化氢化，由对映体过量为17至94％的化合物6制备化合物7，其为合成4-甲氧基香叶烷的前体。使用[Rh（（S，S）-bdpp）（NBD）] ClO 4和[Rh（（R，R）-bdpp）（NBD）] ClO 4在80的氢气压力下获得最佳氢化结果酒吧。
• Stereoselective Synthesis of (<i>R</i>)- and (<i>S</i>)-4-Methoxydalbergione via Asymmetric Catalytic Hydrogenation
  作者：Philippe Bissel、Abdesslame Nazih、Rafaël Sablong、Jean-Pierre Lepoittevin

  DOI：10.1021/ol990961m

  日期：1999.10.1

  [GRAPHICS](R)-(+)- and (S)-(-)-4-methoxydalbergione were synthesized in seven steps with an enantiomeric excess of up to 95% using an asymmetric catalytic hydrogenation step with [Rh((S,S)-bdpp)(NBD)]ClO4 or [Rh((R,R)-bdpp)(NBD)]ClO4, respectively, at a hydrogen pressure of 80 bar. This method should give an easy access to the other members of the dalbergione family.