2,3-dimethyl-1-phenylphosphole

• 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: 2,3-dimethyl-1-phenylphosphole
• 化学式: C₁₂H₁₃P
• 分子量: 188.209
• InChiKey: AZCDDKHXFMVFJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  iron(III) chloride 、 2,3-dimethyl-1-phenylphosphole 在 lithium 、 aluminum (III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以88%的产率得到3,3',4,4'-tetramethyl-1,1'-diphosphaferrocene
  参考文献：
  名称：

  Properties and separation method of enantiomers of the mono- and bis-substituted derivatives of 3,3′,4,4′-tetramethyl-1,1′-diphosphaferrocene: structural analysis using X-ray diffraction and circular dichroism

  摘要：

  This work expands on the recent separation of the enantiomers of the C-2-symmetrical bis-substituted derivatives of 1,1'-diphosphaferrocene. The effective separation of mono-substituted 1,1'-diphosphaferrocenes by the proposed method is demonstrated. The absolute configuration of the three separated components was established using X-ray diffraction. Circular dichroism spectra were collected for all of the separated compounds. The spectrum of each compound shows a characteristic curve, and the curves for the enantiomers are symmetrical. We also show that the correct absolute configuration for similar species can be assigned on the basis of the obtained data. We propose an explanation for the abnormal H-1 NMR spectra of phospholyl protons in some derivatives of 1,1'-diphosphaferrocene. A density functional theory (DFT) study of the conformation, as well as circular dichroism and NMR spectra of the chosen species, is also presented. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.11.003

文献信息

• Properties and separation method of enantiomers of the mono- and bis-substituted derivatives of 3,3′,4,4′-tetramethyl-1,1′-diphosphaferrocene: structural analysis using X-ray diffraction and circular dichroism
  作者：Arkadiusz Kłys、Anna Makal、Anna Zdzienicka

  DOI：10.1016/j.tetasy.2016.11.003

  日期：2017.1

  This work expands on the recent separation of the enantiomers of the C-2-symmetrical bis-substituted derivatives of 1,1'-diphosphaferrocene. The effective separation of mono-substituted 1,1'-diphosphaferrocenes by the proposed method is demonstrated. The absolute configuration of the three separated components was established using X-ray diffraction. Circular dichroism spectra were collected for all of the separated compounds. The spectrum of each compound shows a characteristic curve, and the curves for the enantiomers are symmetrical. We also show that the correct absolute configuration for similar species can be assigned on the basis of the obtained data. We propose an explanation for the abnormal H-1 NMR spectra of phospholyl protons in some derivatives of 1,1'-diphosphaferrocene. A density functional theory (DFT) study of the conformation, as well as circular dichroism and NMR spectra of the chosen species, is also presented. (C) 2016 Elsevier Ltd. All rights reserved.