Triethyl-(2-methylidene-1-naphthalen-2-yloctoxy)silane | 930806-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Triethyl-(2-methylidene-1-naphthalen-2-yloctoxy)silane
• 英文别名: triethyl-(2-methylidene-1-naphthalen-2-yloctoxy)silane
• CAS: 930806-63-6
• 化学式: C₂₅H₃₈OSi
• 分子量: 382.662
• InChiKey: BNSHACDBPXFCIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.43
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Triethyl-(2-methylidene-1-naphthalen-2-yloctoxy)silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  [Ni（NHC）{P（OPh）3}]催化的烯烃和醛的高度选择性偶联：强σ供体和强pi受体之间的协同作用。

  摘要：

  Both a strong electron donor (IPr) and a strong electron acceptor (P(OPh)3) are necessary for a highly selective, nickel-catalyzed coupling reaction between alkenes, aldehydes, and silyltriflates. Without the phosphite, catalysis is not observed and several side reactions are observed. The phosphite appears to suppress the formation of these byproducts and rescue the catalytic cycle by accelerating reductive elimination from an (IPr–Ni–H)(OTf) complex.

  DOI：

  10.1002/anie.200603907
• 作为产物：
  描述：

  辛烯 、 三乙基硅基三氟甲磺酸酯 、 2-萘甲醛 在 bis(1,5-cyclooctadiene)nickel (0) 亚磷酸三苯酯 、 三乙胺 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以99%的产率得到Triethyl-(2-methylidene-1-naphthalen-2-yloctoxy)silane
  参考文献：
  名称：

  [Ni（NHC）{P（OPh）3}]催化的烯烃和醛的高度选择性偶联：强σ供体和强pi受体之间的协同作用。

  摘要：

  Both a strong electron donor (IPr) and a strong electron acceptor (P(OPh)3) are necessary for a highly selective, nickel-catalyzed coupling reaction between alkenes, aldehydes, and silyltriflates. Without the phosphite, catalysis is not observed and several side reactions are observed. The phosphite appears to suppress the formation of these byproducts and rescue the catalytic cycle by accelerating reductive elimination from an (IPr–Ni–H)(OTf) complex.

  DOI：

  10.1002/anie.200603907

文献信息

• Nickel-Catalyzed Coupling of Alkenes, Aldehydes, and Silyl Triflates
  作者：Sze-Sze Ng、Chun-Yu Ho、Timothy F. Jamison

  DOI：10.1021/ja062866w

  日期：2006.9.1

  two recently developed nickel-catalyzed coupling reactions of alkenes, aldehydes, and silyl triflates is presented. These reactions provide either allylic alcohol or homoallylic alcohol derivatives selectively, depending on the ligand employed. These processes are believed to be mechanistically distinct from Lewis acid-catalyzed carbonyl-ene reactions, and several lines of evidence supporting this hypothesis

  介绍了最近开发的烯烃、醛和甲硅烷基三氟甲磺酸酯的两个最近开发的镍催化偶联反应的完整说明。这些反应选择性地提供烯丙醇或高烯丙醇衍生物，这取决于所采用的配体。这些过程被认为在机械上不同于路易斯酸催化的羰基 - 烯反应，并且讨论了支持这一假设的几条证据。
• Highly Selective Coupling of Alkenes and Aldehydes Catalyzed by [Ni(NHC){P(OPh)3}]: Synergy between a Strong σ Donor and a Strong π Acceptor
  作者：Chun-Yu Ho、Timothy F. Jamison

  DOI：10.1002/anie.200603907

  日期：2007.1.22

  Both a strong electron donor (IPr) and a strong electron acceptor (P(OPh)3) are necessary for a highly selective, nickel-catalyzed coupling reaction between alkenes, aldehydes, and silyltriflates. Without the phosphite, catalysis is not observed and several side reactions are observed. The phosphite appears to suppress the formation of these byproducts and rescue the catalytic cycle by accelerating reductive elimination from an (IPr–Ni–H)(OTf) complex.