(R)-tert-butylphenylvinylphosphine oxide | 228113-25-5

• 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: (R)-tert-butylphenylvinylphosphine oxide
• 英文别名: (R_P)-(−)-tert-butylphenylvinylphosphine oxide；(+)-(R)-(tert-Butylvinylphosphinoyl)benzene；[tert-butyl(ethenyl)phosphoryl]benzene
• CAS: 228113-25-5
• 化学式: C₁₂H₁₇OP
• 分子量: 208.24
• InChiKey: NJURNXJVZJJWJX-AWEZNQCLSA-N

物化性质

• 沸点：
  339.1±15.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(-)- α-甲基苄胺 、 (R)-tert-butylphenylvinylphosphine oxide 以 水 为溶剂， 反应 168.0h， 生成 [2-((R)-tert-Butyl-phenyl-phosphinoyl)-ethyl]-((S)-1-phenyl-ethyl)-amine
  参考文献：
  名称：

  Chiral β-aminophosphine oxides as ligands for ruthenium assisted enantioselective transfer hydrogenation of ketones

  摘要：

  Enantiopure B-aminophosphine oxide ligands have been synthesized and used in asymmetric transfer hydrogenation of ketones. Optically active alcohols are obtained in high yields and with up to 84% enantiomeric excess. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00063-4
• 作为产物：
  描述：

  tert-Butylphenylphosphine oxide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 生成 (R)-tert-butylphenylvinylphosphine oxide
  参考文献：
  名称：

  Pietrusiewicz, K. Michal, Phosphorus, Sulfur and Silicon and the Related Elements, 1996, vol. 109, # 1-4, p. 573 - 576

  摘要：

  DOI：

文献信息

• Synthesis of Substituted <i>P</i>-Stereogenic Vinylphosphine Oxides by Olefin Cross-Metathesis
  作者：Oleg M. Demchuk、K. Michał Pietrusiewicz、Anna Michrowska、Karol Grela

  DOI：10.1021/ol035011m

  日期：2003.9.1

  [GRAPHICS]Substituted vinylphosphine oxides have been prepared in good yield and exclusive (E)-olefin selectivity via olefin cross-metathesis using Grubbs and Hoveyda-type ruthenium catalysts. In addition, metathesis of chiral vinylphosphine oxides proceeds without racemization of the phosphorus chirality center, providing easy access to functionalized chiral nonracemic (E)-alkenylphosphine oxides.
• [4 + 2] Cycloaddition of Vinylphosphine Oxides to α-Oxy-<i>o</i>-xylylene as a route to Phosphorylated Naphthyl and Biaryl Scaffolds
  作者：Sławomir Frynas、Elżbieta Łastawiecka、Anna E. Kozioł、Anna Flis、K. Michał Pietrusiewicz

  DOI：10.1021/acs.joc.8b02659

  日期：2019.2.15

  alpha-Oxy-o-xylylene, a highly reactive diene readily accessible from benzocyclobutenol, undergoes Diels-Alder reaction with vinylphosphine oxides, yielding the corresponding 2-phosphorylated 1-hydroxy-1,2,3,4-tetrahydronaphthalenes in excellent yields. Use of unsubstituted and trans-2-aryl-substituted vinylphosphine oxides leads to cycloadducts with complete regioselectivity and with cis/trans selectivity up to 19:1 in the most favorable case. In the case of P-stereogenic trans-2-aryl-substituted vinylphosphine oxides, a virtually complete chirality transfer from P to C can be achieved. Dehydration and aromatization of the obtained cycloadducts bearing the resolved P-stereogenic phosphinoyl groups can be carried out to afford the valuable P-stereogenic and axially chiral phosphorylated 1,2'-binaphthyl ring system. Cases of restricted rotation around Csp(3)-Csp(2) single bond in some tetrahydronaphthalene cycloadducts have also been revealed.