1-(diphenylphosphinoylmethyl)-2-iodobenzene | 1241982-03-5

• 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: 1-(diphenylphosphinoylmethyl)-2-iodobenzene
• 英文别名: 2-(diphenylphosphinylmethyl)iodobenzene；1-(Diphenylphosphorylmethyl)-2-iodobenzene
• CAS: 1241982-03-5
• 化学式: C₁₉H₁₆IOP
• 分子量: 418.214
• InChiKey: QJNFWYOPISCXIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基乙氧基膦 、 邻碘氯苄 以 neat (no solvent) 为溶剂， 反应 1.0h， 以85%的产率得到1-(diphenylphosphinoylmethyl)-2-iodobenzene
  参考文献：
  名称：

  [4 + 2] Cycloaddition of Vinylphosphine Oxides to α-Oxy-o-xylylene as a route to Phosphorylated Naphthyl and Biaryl Scaffolds

  摘要：

  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.

  DOI：

  10.1021/acs.joc.8b02659

文献信息

• Ferrocenyl-Aryl Based trans-Chelating Diphosphine Ligands: Synthesis, Molecular Structure and Application in Enantioselective Hydrogenation
  作者：Raffael Schuecker、Kurt Mereiter、Felix Spindler、Walter Weissensteiner

  DOI：10.1002/adsc.200900906

  日期：——

  the molecular structures in the solid state of two representatives were determined by X‐ray diffraction. High throughput screening of these ligands in rhodium‐, ruthenium‐ and iridium‐mediated hydrogenations of a variety of alkenes and ketones revealed that these ligands can deliver high enantioselectivity for alkenes (up to 98% ee) but are less selective when ketones are used as the substrates. The

  基于二茂铁基-芳基骨架的潜在反式螯合二膦配体以四步顺序合成，并通过X射线衍射确定了两个代表固态的分子结构。在铑，钌和铱介导的各种烯烃和酮加氢中对这些配体的高通量筛选显示，这些配体可对烯烃提供高对映选择性（高达98％ee），但当使用酮作为酮时，选择性较低。基板。在其正方形的平面钯和铂配合物二氯化一个配位体的配位行为进行了研究由31 P NMR和仅反观察到螯合的复合物以及低聚副产物。与（p- cymene）二氯化钌二聚体[RuCl 2（p- cymene）] 2反应，生成非对映体复合物的混合物。