methyl (2,4,6-trimethylphenyl)vinylphosphine oxide | 134817-53-1

• 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: methyl (2,4,6-trimethylphenyl)vinylphosphine oxide
• 英文别名: mesitylmethylvinylphosphine oxide；2-[Ethenyl(methyl)phosphoryl]-1,3,5-trimethylbenzene
• CAS: 134817-53-1
• 化学式: C₁₂H₁₇OP
• 分子量: 208.24
• InChiKey: ZLWSYAIZNRQVHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 、 methyl (2,4,6-trimethylphenyl)vinylphosphine oxide 生成 6,6-dimethyl-2-[methyl-(2,4,6-trimethylphenyl)phosphoryl]-3,3a,4,5-tetrahydro-2H-pyrrolo[1,2-b][1,2]oxazole
  参考文献：
  名称：

  BRANDI, ALBERTO;CICCHI, STEFANO;GOTI, ANDREA;PIETRUSIEWICZ, K. MICHAL;ZAB+, J. ORG. CHEM., 56,(1991) N4, C. 4383-4388

  摘要：

  DOI：

文献信息

• Radical addition to vinylphosphine oxides: 1,2-stereoinduction of phosphorus stercogcnic centre
  作者：Alberto Brandi、Stefano Cicchi、Andrea Goti、K. Michal Pietrusiewiez

  DOI：10.1016/s0040-4039(00)79740-1

  日期：1991.7

  AIBN havebeentrapped by diphenylvinylphosphine oxide 2 giving the addition products 6–8 in high yields. Free radical addition to 2 employing the Barton methodology gave lower yields. The use of chiral (racemic:) vinylphosphine oxides allowed a stereoselective radical addition with a diastercomeric ratio as high as 9:1 for mesitylmethylvinylphosphine oxide 1.

  在AIBN存在下，卤化物3-5与Bu 3 SnH的反应衍生出的碳偏静基团已被二苯基乙烯基氧化膦2截留，从而以高收率得到加成产物6-8。采用Barton方法向2中添加自由基的产率较低。使用手性（外消旋:) vinylphosphine氧化物的所允许的立体选择性基加以作为9 diastercomeric比率高达：1 mesitylmethylvinylphosphine氧化物1。
• Stereoselective nitrone additions to vinylphosphine derivatives: effect of phosphorus substituents on reaction diastereoselectivity
  作者：Alberto Brandi、Stefano Cicchi、Andrea Goti、K. Michal Pietrusiewicz、Maria Zablocka、Witold Wisniewski

  DOI：10.1021/jo00014a011

  日期：1991.7

  Meaningful diastereofacial selectivity in cycloaddition of 2,2-dimethyl-3,4-pyrroline N-oxide (DMPO) to 12 structurally diversified vinylphosphine derivatives 1-12 has been achieved by proper choice of the polar substituent on phosphorus combined with effective steric differentiation of the remaining substituents. The unique sense of induction in all these reactions is consistent with the assumption that vinylphosphorus dipolarophiles prefer an s-cisoid array of C = C - P = X fragments in their reactive conformations. Use of divinylphosphine derivatives in such reactions exemplifies the possibility of synthesizing chiral phosphine oxides and sulfides from prochiral precursors in a highly selective and stereochemically predictable manner. An observation that in P-31 NMR spectra the adducts of type I are uniformly found at lower field than adducts of type II facilitates the stereochemical assignments.
• [3,3-Dimethyl-1-(2-pyridylthio)butyl]methyl(2,4,6-trimethylphenyl)phosphine Oxide
  作者：W. Wieczorek

  DOI：10.1107/s0108270195004100

  日期：1995.10.15

  IN the molecule of [3,3-dimethyl-1-(2-pyridylthio)-butyl]methyl(2,4,6-trimethylphenyl)phosphine oxide, C21H30NOPS, the P=O bond is nearly coplanar with plane are 0.137(1) and 0.038(2)Angstrom, respectively] and nearly parallel to the pyridyl ring [distances of the P and O atoms from the best plane are -1.940(1) and -2.182 (2) Angstrom, respectively].The structure is stabilized by a C11-H111 ... N intramolecular hydrogen bond [H111 ... N 2.37, C11 . bullet>. N 2.915(4)Angstrom, C11-H111 ... N 115 degrees] and a C20-H201 ... O(-1+x, 1/2-y, 1/2+z) intermolecular hydrogen bond [H201 ... O 2.41, C20 ... O 3.254 (4) Angstrom, C20-H201 ... O 148 degrees] (Fig.2).