(+/-)-benzylisopropylphenylphosphine | 162048-18-2

• 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: (+/-)-benzylisopropylphenylphosphine
• 英文别名: Benzyl-phenyl-propan-2-ylphosphane
• CAS: 162048-18-2；71779-62-9
• 化学式: C₁₆H₁₉P
• 分子量: 242.301
• InChiKey: YHMVMOUWTJCKAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (+/-)-benzylisopropylphenylphosphine 在 HCl 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and crystal structure of the unique chiral anion [Re2Cl7PBzMePh]− and the direct determination of its δ-bond energy by molecular modelling

  摘要：

  The quadruply bonded chiral anion [Re(2)Cl(2)PBzMePh](-) (Bz=CH(2)Ph) was synthesized and its crystal structure was determined. It crystallized in space group P (1) over bar with unit cell dimensions a=10.677(2), b=12.220(2), c=18.220(4) Angstrom, alpha=85.66(2>, beta=75.98(2) and gamma= 80.07(2)degrees. The Re-Re distance was 2.2196(8) Angstrom. The average twist angle chi was 11.6 degrees. The delta-bond energy was determined by molecular modelling to be 9 kcal mol(-1) and 5% greater than the energy required to eclipse [Re2Cl8](2-).

  DOI：

  10.1016/0020-1693(94)04232-k
• 作为产物：
  描述：

  isopropyl(phenyl)phosphine oxide 在 四氢呋喃 、 potassium tert-butylate 、 三氯化磷 作用下， 以 正己烷 为溶剂， 反应 8.0h， 生成 (+/-)-benzylisopropylphenylphosphine
  参考文献：
  名称：

  通过醇盐介导的有机硼酸酯脱硼基化直接合成叔膦

  摘要：

  烷基硼的直接转化已成为创建碳-碳和碳-杂原子键的通用且强大的方法。然而，其在碳和磷形成中的潜在应用仍未得到探索。在这项研究中，我们提出了一种醇盐碱促进的反应系统，该系统能够通过选择性 C-B 键断裂对苄基有机硼酸酯和偕双（硼酸酯）进行脱硼基膦化。这种方法可以在温和条件下以良好的产率合成有价值的叔膦。该方法的实用性和工业潜力通过操作简单性、广泛的基质范围和易于扩展性得到强调。

  DOI：

  10.1021/acs.orglett.4c00001

文献信息

• Synthesis and resolution of benzylisopropylphenylphosphine, a monodentate P-chiral ligand
  作者：Joan Albert、Ramón Bosque、J.Magali Cadena、Jaume R Granell*、Guillermo Muller、Juan Ignacio Ordinas

  DOI：10.1016/s0957-4166(00)00300-1

  日期：2000.8

  The synthesis of benzylisopropylphenylphosphine by reaction between the benzylphenylphosphide anion and isopropyl chloride and its subsequent resolution by means of an optically active palladium metallacycle is reported. The synthesis of the organometallic complex [Pd(eta(3)-2-MeC3H4)Cl((PBnPrPh)-Pr-i)] is also described, as well as the assignment of the absolute configuration of the coordinated phosphine by mono- and bidimensional proton NMR spectra, using the homochiral palladacycle as a reference point. In order to estimate the height of the energy barrier corresponding to the rotation of the phosphine ligand around the Pd-P bond, several calculations were performed at the semiempirical PM3(tm) level. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and crystal structure of the unique chiral anion [Re2Cl7PBzMePh]− and the direct determination of its δ-bond energy by molecular modelling
  作者：Patrick McArdle、Mary Rabbitte、Desmond Cunningham

  DOI：10.1016/0020-1693(94)04232-k

  日期：1995.2

  The quadruply bonded chiral anion [Re(2)Cl(2)PBzMePh](-) (Bz=CH(2)Ph) was synthesized and its crystal structure was determined. It crystallized in space group P (1) over bar with unit cell dimensions a=10.677(2), b=12.220(2), c=18.220(4) Angstrom, alpha=85.66(2>, beta=75.98(2) and gamma= 80.07(2)degrees. The Re-Re distance was 2.2196(8) Angstrom. The average twist angle chi was 11.6 degrees. The delta-bond energy was determined by molecular modelling to be 9 kcal mol(-1) and 5% greater than the energy required to eclipse [Re2Cl8](2-).
• Direct Synthesis of Tertiary Phosphines via Alkoxide-Mediated Deborylative Phosphination of Organoboronates
  作者：Huaxing Sun、Jing Wang、Zihang Du、Kun Zhang、Jiefeng Hu、Su Jing

  DOI：10.1021/acs.orglett.4c00001

  日期：2024.3.1

  carbon–heteroatom bonds. However, its potential application in the formation of carbon and phosphorus remains unexplored. In this study, we present an alkoxide base-promoted reaction system that enables deborylative phosphination of benzylic organoboronates and geminal bis(boronates) via selective C–B bond cleavage. This approach allows for the synthesis of valuable tertiary phosphines in good yields under

  烷基硼的直接转化已成为创建碳-碳和碳-杂原子键的通用且强大的方法。然而，其在碳和磷形成中的潜在应用仍未得到探索。在这项研究中，我们提出了一种醇盐碱促进的反应系统，该系统能够通过选择性 C-B 键断裂对苄基有机硼酸酯和偕双（硼酸酯）进行脱硼基膦化。这种方法可以在温和条件下以良好的产率合成有价值的叔膦。该方法的实用性和工业潜力通过操作简单性、广泛的基质范围和易于扩展性得到强调。