tert-butyldivinylphosphine | 124803-13-0

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机膦及其衍生物
• 英文名称: tert-butyldivinylphosphine
• 英文别名: tert-Butyl(diethenyl)phosphane；tert-butyl-bis(ethenyl)phosphane
• CAS: 124803-13-0
• 化学式: C₈H₁₅P
• 分子量: 142.181
• InChiKey: NDAITJNHYYVGCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  tert-butyldivinylphosphine 在 双氧水 作用下， 以 氯仿 、 苯 为溶剂， 反应 360.0h， 生成
  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
• 作为产物：
  描述：

  叔丁基二氯化膦 、 乙烯基溴化镁 以 四氢呋喃 为溶剂， 生成 tert-butyldivinylphosphine
  参考文献：
  名称：

  铑催化的二乙烯基膦氧化物与芳基硼氧烷的对映体选择性加氢芳基化

  摘要：

  铑催化的二乙烯基膦氧化物（RP（O）（CH = CH 2）2）与芳基硼氧烷（（ArBO）3）的氢化芳基化反应生成相应的单芳基化产物（RP（O）（CH = CHAr）CH 2 CH 3）高产。氧化膦中的两个乙烯基之一被氧化芳基化，而另一个被还原为乙基部分。这些反应在（R）-DTBM-segphos / Rh存在的情况下，对映体乙烯基具有很高的选择性，从而使对映体单芳基化产物具有很高的对映选择性。

  DOI：

  10.1002/anie.201712572

文献信息

• Weichmann, H.; Rensch, B.; Dargatz, M., Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 1, p. 1 - 8
  作者：Weichmann, H.、Rensch, B.、Dargatz, M.、Meunier-Piret, J.

  DOI：——

  日期：——
• 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：——
• Rhodium-Catalyzed Enantioposition-Selective Hydroarylation of Divinylphosphine Oxides with Aryl Boroxines
  作者：Zhe Wang、Tamio Hayashi

  DOI：10.1002/anie.201712572

  日期：2018.2.5

  undergoes oxidative arylation while the other one is reduced to an ethyl moiety. These reactions proceed with high selectivity in terms of the enantiotopic vinyl groups in the presence of (R)‐DTBM‐segphos/Rh to give the P‐stereogenic monoarylation products with high enantioselectivity.

  铑催化的二乙烯基膦氧化物（RP（O）（CH = CH 2）2）与芳基硼氧烷（（ArBO）3）的氢化芳基化反应生成相应的单芳基化产物（RP（O）（CH = CHAr）CH 2 CH 3）高产。氧化膦中的两个乙烯基之一被氧化芳基化，而另一个被还原为乙基部分。这些反应在（R）-DTBM-segphos / Rh存在的情况下，对映体乙烯基具有很高的选择性，从而使对映体单芳基化产物具有很高的对映选择性。
• 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.