N,P-diisopropyl-N-methyl-2-phosphanylaniline | 1609397-01-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,P-diisopropyl-N-methyl-2-phosphanylaniline
• CAS: 1609397-01-4
• 化学式: C₁₃H₂₂NP
• 分子量: 223.298
• InChiKey: IVTYAIDDBIMENB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  N-methyl-2-phosphanylaniline 、 2-溴丙烷 在 氨 、 sodium 作用下， 以 乙醚 为溶剂， 反应 0.17h， 生成 N-methyl-2-isopropylphosphanylaniline 、 N,P-diisopropyl-N-methyl-2-phosphanylaniline
  参考文献：
  名称：

  Benzazaphospholine-2-carboxylic acids: Synthesis, structure and properties of heterocyclic phosphanyl amino acids

  摘要：

  1,3-Dialkyl-1,3-benzazaphospholine-2-carboxylic acids 2a,b can be conveniently prepared by metalation and alkylation of N-methyl- and N-neopentyl-o-phosphanylaniline in liquid ammonia and cyclocondensation of the resulting N,P-disecondary phosphanylanilines 1a,b with glyoxylic acid hydrate (GAH) in ether. The primary neopentylphosphanylaniline reacts with two equivalents of GAH and forms a phosphanyl-bis(amino acid) 3 with toluidine. alpha-Branched P-substituents induce strongly preferred formation of trans-diastereoisomers with R,R- and S,S-configuration at P and C2, as shown by a crystal structure analysis of 2a, whereas a P-neopentyl (P-Np) group gives rise to trans/cis-diastereoisomeric mixtures. The trans-configuration exhibits the P lone-pair in cis-position to the COOH group, suitable for formation of five-membered chelate rings, as in diphenylphosphanylacetate nickel catalysts for ethylene oligomerization. Screening of 2a,b/Ni(COD)(2) solutions in THF by a batch procedure indeed showed formation of catalysts for conversion of ethylene to linear oligomers and waxy low-molecular weight polymers. The conversion depends strongly on the size of the N-alkyl group, being slow and limited for the N-Me catalyst 2a/Ni and much faster and more complete for the N-Np-substituted catalysts 2b/Ni and 2c/Ni (N-Np, P-tBu). Comparison of 2b/Ni with 2c/Ni shows that the more bulky P-substituent further increases the catalyst activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.046