Di-(2-furyl)-phenylphosphinoxid | 40927-84-2

• 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: Di-(2-furyl)-phenylphosphinoxid
• 英文别名: 2-[Furan-2-yl(phenyl)phosphoryl]furan；2-[furan-2-yl(phenyl)phosphoryl]furan
• CAS: 40927-84-2
• 化学式: C₁₄H₁₁O₃P
• 分子量: 258.213
• InChiKey: XOJUKISEFPJQCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  生成 Di-(2-furyl)-phenylphosphinoxid
  参考文献：
  名称：

  Electronic Properties of Furyl Substituents at Phosphorus and Their Influence on ³¹P NMR Chemical Shifts

  摘要：

  The electronic properties of 2-furyl and 3-furyl substituents attached to phosphanes and phosphonium salts were studied by means of IR spectroscopy and experimental and computational P-31 NMR spectroscopy. The heteroaromatic systems proved to be electron withdrawing with respect to phenyl substituents. However, phosphorus atoms with attached furyl substituents are strongly shielded in NMR. The reason for this phenomenon was studied by solid state P-31 MAS NMR experiments. The chemical shift tensor was extracted, and the orientation within the molecules was determined. The tensor component sigma(33), which is effected the most by furyl systems, is oriented perpendicular to the P-C bonds of the substituents. P-furyl bonds are shorter than P-phenyl bonds. We assume therefore a lower ground-state energy of the molecules, because of the electron withdrawing properties of the 2-furyl systems. The sigma(para) component of the P-31 NMR magnetic shielding is therefore smaller, which results in an overall increase of the magnetic shielding.

  DOI：

  10.1021/ja057085u

文献信息

• A Wittig Reaction with 2-Furyl Substituents at the Phosphorus Atom: Improved (Z) Selectivity and Isolation of a Stable Oxaphosphetane Intermediate
  作者：Marco Appel、Steffen Blaurock、Stefan Berger

  DOI：10.1002/1099-0690(200204)2002:7<1143::aid-ejoc1143>3.0.co;2-g

  日期：2002.4

  Wittig reactions with ylides bearing one, two or three 2-furyl groups directly bound to the phosphorus atom have been studied. Greatly improved (Z)-alkene selectivities of up to 98:2 could be observed if 2-furyl groups were present. Monitoring of the reactions by NMR spectroscopy revealed only oxaphosphetane intermediates, which became more stable with increasing number of 2-furyl substituents bound

  已经研究了与带有一个、两个或三个直接与磷原子结合的 2-呋喃基的叶立德的 Wittig 反应。如果存在 2-呋喃基，则可以观察到高达 98:2 的 (Z)-烯烃选择性大大提高。通过 NMR 光谱对反应的监测显示只有氧代膦烷中间体，随着与磷原子结合的 2-呋喃基取代基数量的增加，中间体变得更加稳定。Oxaphosphetane 10d 与三个呋喃基团被成功分离，并提供了晶体结构分析的结果。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)