Bis(3,5-di-tert-butylphenyl)phosphinic acid | 157247-80-8

• 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: Bis(3,5-di-tert-butylphenyl)phosphinic acid
• CAS: 157247-80-8
• 化学式: C₂₈H₄₃O₂P
• 分子量: 442.622
• InChiKey: XMZDPCJGWHTROD-UHFFFAOYSA-N

物化性质

• 沸点：
  538.9±50.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Bis(3,5-di-tert-butylphenyl)phosphinic acid 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 生成 Bis(3,5-di-tert-butylphenyl)phosphinyl chloride
  参考文献：
  名称：

  Cationic BINAP-Ru(II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of .alpha.- and .beta.-Functionalized Ketones

  摘要：

  Cationic ruthenium-BINAP complexes 5, 7, and 10 of the formula [RuX((S)-BINAP) (arene)]Y, where X = Cl, Br, I; Y = Cl, Br, I, BF4, B(C6H5)(4); arene = benzene, p-cymene, ethyl benzoate, and their enantiomers have been prepared by the reaction of arene-ruthenium halide complexes 4, 6, and 9 with (S)-BINAP or (R)-BINAP. Structures of the complexes were established by spectroscopy, conductivity, and a single-crystal X-ray analysis (5d: orthorhombic, P2(1)2(1)2; a 20.141(2) Angstrom, b = 18.504(1) Angstrom, c 12.241(1) Angstrom V = 4562.0(7) Angstrom(3), Z = 4, R = 0.078 for unique 4177 reflections). BINAP derivatives with various substituents at the para and meta positions of four phenyl rings on phosphorus atoms and their cationic Ru(II) complexes have also been synthesized. These BINAP-Ru(II) complexes have been used as catalysts for the asymmetric hydrogenation of various unsaturated organic compounds such as alpha- and beta-keto esters, allylic alcohols, and alpha,beta-unsaturated carboxylic acids in excellent diastereo- and/or enantioselectivities. Catalytic activities and stereoselectivities depend highly on reaction conditions such as solvent, temperature, and additives. Variation of halogen ligands bound to ruthenium atom and substituents on four phenyl rings of BINAP also have exerted remarkable effects on the efficiency of the catalysis. Asymmetric hydrogenation of methyl (+/-)-2-(benzamidomethyl)-3-oxobutanoate catalyzed by the species derived from 9c and 3,5((t)Bu)(2)-BINAP afforded the corresponding syn-(2S,3R)-17 in 98% de and 99% ee.

  DOI：

  10.1021/jo00090a026
• 作为产物：
  描述：

  3,5-二叔丁基溴苯 在 二乙基二氯膦酰胺 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成 Bis(3,5-di-tert-butylphenyl)phosphinic acid
  参考文献：
  名称：

  Cationic BINAP-Ru(II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of .alpha.- and .beta.-Functionalized Ketones

  摘要：

  Cationic ruthenium-BINAP complexes 5, 7, and 10 of the formula [RuX((S)-BINAP) (arene)]Y, where X = Cl, Br, I; Y = Cl, Br, I, BF4, B(C6H5)(4); arene = benzene, p-cymene, ethyl benzoate, and their enantiomers have been prepared by the reaction of arene-ruthenium halide complexes 4, 6, and 9 with (S)-BINAP or (R)-BINAP. Structures of the complexes were established by spectroscopy, conductivity, and a single-crystal X-ray analysis (5d: orthorhombic, P2(1)2(1)2; a 20.141(2) Angstrom, b = 18.504(1) Angstrom, c 12.241(1) Angstrom V = 4562.0(7) Angstrom(3), Z = 4, R = 0.078 for unique 4177 reflections). BINAP derivatives with various substituents at the para and meta positions of four phenyl rings on phosphorus atoms and their cationic Ru(II) complexes have also been synthesized. These BINAP-Ru(II) complexes have been used as catalysts for the asymmetric hydrogenation of various unsaturated organic compounds such as alpha- and beta-keto esters, allylic alcohols, and alpha,beta-unsaturated carboxylic acids in excellent diastereo- and/or enantioselectivities. Catalytic activities and stereoselectivities depend highly on reaction conditions such as solvent, temperature, and additives. Variation of halogen ligands bound to ruthenium atom and substituents on four phenyl rings of BINAP also have exerted remarkable effects on the efficiency of the catalysis. Asymmetric hydrogenation of methyl (+/-)-2-(benzamidomethyl)-3-oxobutanoate catalyzed by the species derived from 9c and 3,5((t)Bu)(2)-BINAP afforded the corresponding syn-(2S,3R)-17 in 98% de and 99% ee.

  DOI：

  10.1021/jo00090a026

文献信息

• SO₂F₂-Mediated Fluorination of P(O)–H and P(O)–OH Compounds under Mild Conditions
  作者：Guo-Fu Zhang、Lin-Jun Han、Chen-Fei Guan、Cheng-Rong Ding

  DOI：10.1021/acs.joc.3c01364

  日期：2023.9.15

  fluorine compounds in the pharmaceutical industry, their synthesis has attracted great attention. Herein, we report an efficient fluorination strategy for P(O)–H and P(O)–OH compounds using sulfuryl fluoride as the fluorination reagent. Avoiding the use of expensive or complex prepreparation reagents for fluoridation, this strategy could conveniently construct a variety of fluorophosphonates and phosphonofluoridates

  随着有机磷氟化合物在制药工业中的重要性日益增加，其合成引起了极大的关注。在此，我们报告了一种使用硫酰氟作为氟化试剂对 P(O)-H 和 P(O)-OH 化合物进行有效氟化的策略。该策略避免了使用昂贵或复杂的氟化制备试剂，可以在温和条件下且无需额外氧化剂的情况下方便地构建各种氟膦酸盐和膦酰氟酸盐。