(+/-)-(2-Acetoxy-1-naphthyl)methylphenylphosphine oxide | 160722-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-(2-Acetoxy-1-naphthyl)methylphenylphosphine oxide
• 英文别名: [1-[Methyl(phenyl)phosphoryl]naphthalen-2-yl] acetate
• CAS: 160722-05-4
• 化学式: C₁₉H₁₇O₃P
• 分子量: 324.316
• InChiKey: IUBLZIRTNRHKAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(2-Acetoxy-1-naphthyl)methylphenylphosphine oxide 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 43.0h， 生成 (S)-(+)-(2-Methoxy-1-naphthyl)methylphenylphosphine oxide
  参考文献：
  名称：

  Kinetic Resolution of Phosphines and Phosphine Oxides with Phosphorus Stereocenters by Hydrolases

  摘要：

  Lipase from Candida rugosa (CRL) and cholesterol esterase (CE) catalyzed the enantioselective hydrolysis of pendant acetates in chiral phosphines and phosphine oxides. The enantioselectivity for most substrates was modest (E = 1.5-4.8), but both hydrolases showed high enantioselectivity for one substrate, ArPhMeP=O (Ar = 1-(2-acetoxy)naphthyl, 4c), E = 81 (CRL) and 32 (GE). Preparative-scale resolution of (+/-)-4c (1.0 g) catalyzed by CRL yielded enantiomerically-enriched starting acetate, (S)-(+)-4c, 0.48 g, 90% ee as well as product alcohol, (R)(-)-4b (Ar = 1-(2-hydroxy)naphthyl), 0.39 g, 88% se. Recrystallization of 4b from toluene raised the enantiomeric purity to >95% ee. Standard chemical steps followed by stereospecific reduction gave both enantiomers of phosphine ArPhMeP (Ar = 1-(2-methoxy)naphthyl) with 96-97% ee. This phosphine is an analog of PAMP (Ar = 2-methoxyphenyl), a chiral phosphine used in asymmetric synthesis.

  DOI：

  10.1021/jo00104a015
• 作为产物：
  描述：

  (+/-)-(2-Methoxy-1-naphthyl)methylphenylphosphine oxide 在 4-二甲氨基吡啶 、 三溴化硼 、 sodium carbonate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 25.0h， 生成 (+/-)-(2-Acetoxy-1-naphthyl)methylphenylphosphine oxide
  参考文献：
  名称：

  Kinetic Resolution of Phosphines and Phosphine Oxides with Phosphorus Stereocenters by Hydrolases

  摘要：

  Lipase from Candida rugosa (CRL) and cholesterol esterase (CE) catalyzed the enantioselective hydrolysis of pendant acetates in chiral phosphines and phosphine oxides. The enantioselectivity for most substrates was modest (E = 1.5-4.8), but both hydrolases showed high enantioselectivity for one substrate, ArPhMeP=O (Ar = 1-(2-acetoxy)naphthyl, 4c), E = 81 (CRL) and 32 (GE). Preparative-scale resolution of (+/-)-4c (1.0 g) catalyzed by CRL yielded enantiomerically-enriched starting acetate, (S)-(+)-4c, 0.48 g, 90% ee as well as product alcohol, (R)(-)-4b (Ar = 1-(2-hydroxy)naphthyl), 0.39 g, 88% se. Recrystallization of 4b from toluene raised the enantiomeric purity to >95% ee. Standard chemical steps followed by stereospecific reduction gave both enantiomers of phosphine ArPhMeP (Ar = 1-(2-methoxy)naphthyl) with 96-97% ee. This phosphine is an analog of PAMP (Ar = 2-methoxyphenyl), a chiral phosphine used in asymmetric synthesis.

  DOI：

  10.1021/jo00104a015

文献信息

• Kinetic Resolution of Phosphines and Phosphine Oxides with Phosphorus Stereocenters by Hydrolases
  作者：Alessio N. Serreqi、Romas J. Kazlauskas

  DOI：10.1021/jo00104a015

  日期：1994.12

  Lipase from Candida rugosa (CRL) and cholesterol esterase (CE) catalyzed the enantioselective hydrolysis of pendant acetates in chiral phosphines and phosphine oxides. The enantioselectivity for most substrates was modest (E = 1.5-4.8), but both hydrolases showed high enantioselectivity for one substrate, ArPhMeP=O (Ar = 1-(2-acetoxy)naphthyl, 4c), E = 81 (CRL) and 32 (GE). Preparative-scale resolution of (+/-)-4c (1.0 g) catalyzed by CRL yielded enantiomerically-enriched starting acetate, (S)-(+)-4c, 0.48 g, 90% ee as well as product alcohol, (R)(-)-4b (Ar = 1-(2-hydroxy)naphthyl), 0.39 g, 88% se. Recrystallization of 4b from toluene raised the enantiomeric purity to >95% ee. Standard chemical steps followed by stereospecific reduction gave both enantiomers of phosphine ArPhMeP (Ar = 1-(2-methoxy)naphthyl) with 96-97% ee. This phosphine is an analog of PAMP (Ar = 2-methoxyphenyl), a chiral phosphine used in asymmetric synthesis.