2-[(S)-(1-(p-methylphenyl)ethyl)amino]benzenephosphonic acid diethyl ester | 1542703-67-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[(S)-(1-(p-methylphenyl)ethyl)amino]benzenephosphonic acid diethyl ester
• CAS: 1542703-67-2
• 化学式: C₁₉H₂₆NO₃P
• 分子量: 347.394
• InChiKey: MCHDWMZFMXUNQS-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[(S)-(1-(p-methylphenyl)ethyl)amino]benzenephosphonic acid diethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 72.0h， 以74%的产率得到N-[(S)-1-(p-methylphenyl)ethyl]-2-phosphinoaniline
  参考文献：
  名称：

  Enantiomerically Pure N Chirally Substituted 1,3-Benzazaphospholes: Synthesis, Reactivity toward tBuLi, and Conversion to Functionalized Benzazaphospholes and Catalytically Useful Dihydrobenzazaphospholes

  摘要：

  Catalytic C-P coupling of chiral o-bromoanilines 1a-c to the corresponding o-phosphonoanilines 2a-c, reduction to the phosphines 3a-c, and final acid-catalyzed cyclocondensation represents a convenient access to the title compounds 4-c. Reaction of 4a,b with tBuLi allows solvent-dependent directed lithiation leading either to 2-lithiobenzazaphospholes with a P=CLi NR substructure (in Et2O/KOtBu), in the case of anisyl substitution accompanied by partial additional lithiation in o-position of the MeO-group, or to regiospecific "normal" addition with formation of -P-(tBu)-CHLi-NR- species. These were trapped by ClSiMe3, CO2, or MeOH to give the corresponding substitution products 7b, 8b, 10b, 11a,b and 12a,b, respectively. 12a,b, containing the P-C-COOH structural unit, forms with Ni(COD)(2) in THF very efficient ethylene oligomerization catalysts With high selectivity for linear alpha-olefins. The structure elucidation of the products is based on conclusive solution NMR data and crystal structure analyses of the 1-(1S)-anisylethyl compounds 3b and 4b.

  DOI：

  10.1021/om401184n
• 作为产物：
  描述：

  1,2-二溴苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium isobutoxide 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 palladium dichloride 作用下， 以 甲苯 为溶剂， 反应 28.0h， 生成 2-[(S)-(1-(p-methylphenyl)ethyl)amino]benzenephosphonic acid diethyl ester
  参考文献：
  名称：

  Enantiomerically Pure N Chirally Substituted 1,3-Benzazaphospholes: Synthesis, Reactivity toward tBuLi, and Conversion to Functionalized Benzazaphospholes and Catalytically Useful Dihydrobenzazaphospholes

  摘要：

  Catalytic C-P coupling of chiral o-bromoanilines 1a-c to the corresponding o-phosphonoanilines 2a-c, reduction to the phosphines 3a-c, and final acid-catalyzed cyclocondensation represents a convenient access to the title compounds 4-c. Reaction of 4a,b with tBuLi allows solvent-dependent directed lithiation leading either to 2-lithiobenzazaphospholes with a P=CLi NR substructure (in Et2O/KOtBu), in the case of anisyl substitution accompanied by partial additional lithiation in o-position of the MeO-group, or to regiospecific "normal" addition with formation of -P-(tBu)-CHLi-NR- species. These were trapped by ClSiMe3, CO2, or MeOH to give the corresponding substitution products 7b, 8b, 10b, 11a,b and 12a,b, respectively. 12a,b, containing the P-C-COOH structural unit, forms with Ni(COD)(2) in THF very efficient ethylene oligomerization catalysts With high selectivity for linear alpha-olefins. The structure elucidation of the products is based on conclusive solution NMR data and crystal structure analyses of the 1-(1S)-anisylethyl compounds 3b and 4b.

  DOI：

  10.1021/om401184n