2-hexyl-3-(4'-chlorophenyl)-3-(triethylsiloxy)prop-1-ene

• 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: 2-hexyl-3-(4'-chlorophenyl)-3-(triethylsiloxy)prop-1-ene
• 英文别名: [1-(4-Chlorophenyl)-2-methylideneoctoxy]-triethylsilane；[1-(4-chlorophenyl)-2-methylideneoctoxy]-triethylsilane
• 化学式: C₂₁H₃₅ClOSi
• 分子量: 367.047
• InChiKey: FKHMIWQKJCMCLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.93
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2-hexyl-3-(4'-chlorophenyl)-3-(triethylsiloxy)prop-1-ene 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 、 4-氯苯甲醛 在 亚磷酸三苯酯 、 C₄₂H₅₆ClN₃Ni 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以78%的产率得到2-hexyl-3-(4'-chlorophenyl)-3-(triethylsiloxy)prop-1-ene
  参考文献：
  名称：

  用于 C−C 和 C−N 键形成反应的台式稳定 N-杂环卡宾镍预催化剂

  摘要：

  在此，我们介绍了一类新型的实验室稳定的N杂环卡宾 (NHC) 镍预催化剂，用于均相镍催化。通过提出的 Heck 型机制，镍 (II) 配合物在温和条件下很容易原位活化为 Ni 0 。该预催化剂被证明可以促进羰基、加氢烯基化和胺化反应。

  DOI：

  10.1002/cctc.201800454

文献信息

• Nitrile assisted, Brønsted acid catalyzed regio and stereoselective diarylphosphonylation of allyl silyl ethers
  作者：Chun-Yu Ho、Chun-Wa Chan、Siu-Kwan Wo、Zhong Zuo、Lai-Ying Chan

  DOI：10.1039/c001660h

  日期：——

  for the regio- and stereoselective synthesis of trisubstituted allyl diarylphosphonates from the corresponding disubstituted allyl silyl ethers, circumventing the challenges related to the preparation and availability of stereodefined trisubstituted olefins. A closely related arylation reaction was also discovered during the methodology development. By simply switching the reaction medium, high phos

  我们已经发现了从相应的二取代的烯丙基甲硅烷基醚的区域和立体选择性合成三取代的烯丙基二芳基膦酸酯的温和的催化方案，规避了与立体定义的三取代的烯烃的制备和可用性有关的挑战。在方法开发过程中还发现了一个密切相关的芳基化反应。通过简单地切换反应介质，可以实现高的膦酰化/芳基化比，反之亦然。这可能不是改变溶剂极性的直接结果。评价烯丙基二芳基膦酸酯作为羧酸酯酶抑制剂，筛选结果表明，抑制效率与烯烃和芳基取代基的选择高度相关。
• Platinum-Catalyzed One-Pot Alkenylation of Aldehydes Using Alkynes and Triethylsilane: Dual Catalysis by Platinum(II) Chloride
  作者：Hidenori Kinoshita、Ryousuke Uemura、Daiki Fukuda、Katsukiyo Miura

  DOI：10.1021/ol4026952

  日期：2013.11

  The PtCl2-catalyzed hydrosilylation of terminal alkynes with triethylsilane and subsequent alkenylation of aldehydes with the resultant (E)-alkenylsilanes in a one-pot manner are described. By adding p-benzoquinone and Lil, the latter alkenylation step proceeds smoothly to give allyl silyl ethers in moderate to high yields. This one-pot alkenylation is tolerant to a reasonable range of functional groups. PtCl2 plays a dual role as hydrosilylation and alkenylation catalysts.
• 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.
• Bench-Stable <i>N</i> -Heterocyclic Carbene Nickel Precatalysts for C−C and C−N Bond-Forming Reactions
  作者：Felix Strieth-Kalthoff、Ashley R. Longstreet、Jessica M. Weber、Timothy F. Jamison

  DOI：10.1002/cctc.201800454

  日期：2018.7.9

  Herein, we introduce a new class of bench‐stable N‐heterocyclic carbene (NHC) nickel‐precatalysts for homogeneous nickel‐catalysis. The nickel(II) complexes are readily activated to Ni0 in situ under mild conditions, via a proposed Heck‐type mechanism. The precatalysts are shown to facilitate carbonyl‐ene, hydroalkenylation, and amination reactions.

  在此，我们介绍了一类新型的实验室稳定的N杂环卡宾 (NHC) 镍预催化剂，用于均相镍催化。通过提出的 Heck 型机制，镍 (II) 配合物在温和条件下很容易原位活化为 Ni 0 。该预催化剂被证明可以促进羰基、加氢烯基化和胺化反应。