3-methoxyphenyl(1-naphthyl)phenylphosphine | 1246513-56-3

• 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-methoxyphenyl(1-naphthyl)phenylphosphine
• 英文别名: (3-methoxyphenyl)-naphthalen-1-yl-phenylphosphane
• CAS: 1246513-56-3
• 化学式: C₂₃H₁₉OP
• 分子量: 342.377
• InChiKey: KYOOAEZSRZWEKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methoxyphenyl(1-naphthyl)phenylphosphine 、 (1R,2S,5R)-menthol bromoacetate 以 苯 为溶剂， 反应 22.0h， 以96%的产率得到(2-isopropyl-5-methylcyclohexyloxycarbonylmethyl)(3-methoxyphenyl)(naphthalen-1-yl)phenylphosphonium bromide
  参考文献：
  名称：

  Efficient oxidative resolution of a P-stereogenic triarylphosphine and asymmetric synthesis of a P-stereogenic atropoisomeric biphenyl diphosphine dioxide

  摘要：

  Racemic 3-methoxyphenyl(1-naphthyl)phenylphosphine 1 was effectively resolved via an oxidative resolution procedure utilizing L-menthyl bromoacetate as the resolving agent to give enantiopure 3-methoxyphenyl(1-naphthyl)phenylphosphine oxide (R)-2 in 41% yield. Reduction of the resolved (R)-4 with HSiCl3/NEt3 provided the corresponding phosphine (R)-1 in >97% ee. Ortho-iodination of the enantiopure (R)-4 followed by Ullmann coupling of the resulting iodoarylphosphine oxide gave a P-stereogenic and atropoisomeric biphenyl diphosphine dioxide as a single diastereoisomer. The latter transformation constitutes the first example of an effective transfer of a P-centered chirality to an axial chirality of the atropoisomeric biaryl system. The absolute configurations of the resolved phosphine and the atropoisomeric biaryl system have also been established. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.014
• 作为产物：
  描述：

  间溴苯甲醚 、 Phenyl-α-naphthyl-chlor-phosphin 在 magnesium 作用下， 以 乙醚 为溶剂， 反应 6.5h， 以61.3%的产率得到3-methoxyphenyl(1-naphthyl)phenylphosphine
  参考文献：
  名称：

  Efficient oxidative resolution of a P-stereogenic triarylphosphine and asymmetric synthesis of a P-stereogenic atropoisomeric biphenyl diphosphine dioxide

  摘要：

  Racemic 3-methoxyphenyl(1-naphthyl)phenylphosphine 1 was effectively resolved via an oxidative resolution procedure utilizing L-menthyl bromoacetate as the resolving agent to give enantiopure 3-methoxyphenyl(1-naphthyl)phenylphosphine oxide (R)-2 in 41% yield. Reduction of the resolved (R)-4 with HSiCl3/NEt3 provided the corresponding phosphine (R)-1 in >97% ee. Ortho-iodination of the enantiopure (R)-4 followed by Ullmann coupling of the resulting iodoarylphosphine oxide gave a P-stereogenic and atropoisomeric biphenyl diphosphine dioxide as a single diastereoisomer. The latter transformation constitutes the first example of an effective transfer of a P-centered chirality to an axial chirality of the atropoisomeric biaryl system. The absolute configurations of the resolved phosphine and the atropoisomeric biaryl system have also been established. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.014

文献信息

• Efficient oxidative resolution of a P-stereogenic triarylphosphine and asymmetric synthesis of a P-stereogenic atropoisomeric biphenyl diphosphine dioxide
  作者：Kamil Dziuba、Anna Flis、Anna Szmigielska、K. Michał Pietrusiewicz

  DOI：10.1016/j.tetasy.2010.06.014

  日期：2010.6

  Racemic 3-methoxyphenyl(1-naphthyl)phenylphosphine 1 was effectively resolved via an oxidative resolution procedure utilizing L-menthyl bromoacetate as the resolving agent to give enantiopure 3-methoxyphenyl(1-naphthyl)phenylphosphine oxide (R)-2 in 41% yield. Reduction of the resolved (R)-4 with HSiCl3/NEt3 provided the corresponding phosphine (R)-1 in >97% ee. Ortho-iodination of the enantiopure (R)-4 followed by Ullmann coupling of the resulting iodoarylphosphine oxide gave a P-stereogenic and atropoisomeric biphenyl diphosphine dioxide as a single diastereoisomer. The latter transformation constitutes the first example of an effective transfer of a P-centered chirality to an axial chirality of the atropoisomeric biaryl system. The absolute configurations of the resolved phosphine and the atropoisomeric biaryl system have also been established. (C) 2010 Elsevier Ltd. All rights reserved.