tert-butyldivinylphosphine sulphide | 134817-55-3

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机硫代磷化合物
• 英文名称: tert-butyldivinylphosphine sulphide
• 英文别名: Tert-butyl-bis(ethenyl)-sulfanylidene-lambda5-phosphane；tert-butyl-bis(ethenyl)-sulfanylidene-λ5-phosphane
• CAS: 134817-55-3
• 化学式: C₈H₁₅PS
• 分子量: 174.247
• InChiKey: XKBIUVRUVCMYEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.1
• 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 、 tert-butyldivinylphosphine sulphide 生成 tert-butyl-(6,6-dimethyl-3,3a,4,5-tetrahydro-2H-pyrrolo[1,2-b][1,2]oxazol-2-yl)-ethenyl-sulfanylidene-λ5-phosphane
  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：
• 作为产物：
  描述：

  tert-butyldivinylphosphine 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 苯 为溶剂， 生成 tert-butyldivinylphosphine sulphide
  参考文献：
  名称：

  Stereoselective nitrone additions to vinylphosphine derivatives: effect of phosphorus substituents on reaction diastereoselectivity

  摘要：

  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.

  DOI：

  10.1021/jo00014a011

文献信息

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

  DOI：——

  日期：——
• 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.