(E)-tert-butyl 4-(2-(tert-butyldimethylsilyloxy)phenyl)-2-butenoate | 1019646-06-0

• 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: (E)-tert-butyl 4-(2-(tert-butyldimethylsilyloxy)phenyl)-2-butenoate
• 英文别名: (E)-t-butyl 4-(2-((t-butyldimethylsilyl)oxy)phenyl)but-2-enoate；tert-butyl (E)-4-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]but-2-enoate
• CAS: 1019646-06-0
• 化学式: C₂₀H₃₂O₃Si
• 分子量: 348.558
• InChiKey: VHLKDEZVAMITLT-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸叔丁酯 、 1-tert-butyldimethylsilyloxy-2-(2-propenyl)benzene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 水 为溶剂， 反应 12.0h， 以91%的产率得到(E)-tert-butyl 4-(2-(tert-butyldimethylsilyloxy)phenyl)-2-butenoate
  参考文献：
  名称：

  TPGS-750-M：用于室温下水中金属催化交叉偶联的第二代两亲物

  摘要：

  一种环境友好的表面活性剂 (TPGS-750-M)，一种由外消旋 α-生育酚、MPEG-750 和琥珀酸组成的二酯，已被设计并易于制备为一种有效的纳米胶束形成物质，通常用于金属催化交叉- 水中的偶联反应。已经使用该技术研究了几种“名称”反应，包括 Heck、Suzuki-Miyaura、Sonogashira 和 Negishi-like 偶联，以及胺化、CH 活化和烯烃复分解反应。DLS 和冷冻 TEM 测量形式的物理数据表明，颗粒大小和形状是实现高水平转化的关键因素，因此，产品的分离产率很高。这种新的两亲物将很快上市。

  DOI：

  10.1021/jo101974u

文献信息

• Surfactant-Enabled Transition Metal-Catalyzed Chemistry
  申请人：Berl Volker

  公开号：US20110130562A1

  公开（公告）日：2011-06-02

  In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions.

  本申请公开了一种组合物，包括(a)至少占组合物总重量1%的水；(b)过渡金属催化剂；以及(c)一种或多种增溶剂；以及使用该组合物进行过渡金属介导的键形成反应的方法。
• Rate Enhanced Olefin Cross-Metathesis Reactions: The Copper Iodide Effect
  作者：Karl Voigtritter、Subir Ghorai、Bruce H. Lipshutz

  DOI：10.1021/jo200360s

  日期：2011.6.3

  Copper iodide has been shown to be an effective cocatalyst for the olefin cross-metathesis reaction. In particular, it has both a catalyst stabilizing effect due to iodide ion, as well as copper(I)-based phosphine-scavenging properties that apply to use of the Grubbs-2 catalyst. A variety of Michael acceptors and olefinic partners can be cross-coupled under mild conditions in refluxing diethyl ether

  碘化铜已被证明是烯烃交叉复分解反应的有效助催化剂。特别是，它既具有碘离子带来的催化剂稳定作用，又具有适用于Grubbs-2催化剂的铜(I)基膦清除性能。各种迈克尔受体和烯属配偶体可以在温和条件下在回流乙醚中交叉偶联，避免使用氯化溶剂。使用新型表面活性剂 TPGS-750-M，这种效应也应用于室温水中的化学。
• Olefin Cross-Metathesis Reactions at Room Temperature Using the Nonionic Amphiphile “PTS”:  Just Add Water
  作者：Bruce H. Lipshutz、Grant T. Aguinaldo、Subir Ghorai、Karl Voigtritter

  DOI：10.1021/ol800028x

  日期：2008.4.1

  cross-metathesis reactions in water, involving water-insoluble substrates, at room temperature and using commercially available catalysts are reported. The key to success is to include small percentages of the nonionic, vitamin E-based amphiphile "PTS". The nanometer micelles formed accommodate water-insoluble substrates, along with a readily available Ru-based metathesis catalyst. Reactions proceed

  报道了在室温下并使用可商购的催化剂在水中的不对称烯烃交叉复分解反应的第一个实例，涉及不溶于水的底物。成功的关键是包含少量非离子的，基于维生素E的两亲物“ PTS”。形成的纳米胶束可容纳水不溶性底物，以及易于获得的Ru基复分解催化剂。反应在环境温度下高效且极高的E选择性进行，产物易于分离。
• Surfactant-enabled transition metal-catalyzed chemistry
  申请人：Berl Volker

  公开号：US08785665B2

  公开（公告）日：2014-07-22

  In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions.

  在一种实施例中，本申请公开了混合物，包括(a)至少占混合物1%重量/重量的水；(b)过渡金属催化剂；和(c)一种或多种溶解剂，以及使用这种混合物进行过渡金属介导的键合反应的方法。
• “Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature
  作者：Piyatida Klumphu、Bruce H. Lipshutz

  DOI：10.1021/jo401744b

  日期：2014.2.7

  The third-generation designer amphiphile/surfactant, "Nok" (i.e., SPGS-550-M; beta-sitosterol methoxypolyethyleneglycol succinate), soon to be commercially available from Aldrich, can be prepared in two steps using an abundant plant feedstock and beta-sitosterol, together with succinic anhydride and PEG-550-M. Upon dissolution in water, it forms nanomicelles that serve as nanoreactors, which can be characterized by both cryo-TEM and dynamic light scattering analyses. Several transition-metal-catalyzed reactions have been run under micellar conditions to evaluate this surfactant relative to results obtained in nanoparticles composed of TPGS-750-M (i.e., a second-generation surfactant). It is shown that Nok usually affords yields that are, in general, as good or better than those typically obtained with TPGS-750-M, and yet is far less costly.