三甲基[(1-苯基-3-丁烯基)氧基]硅烷 | 139284-72-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 三甲基[(1-苯基-3-丁烯基)氧基]硅烷
• 英文名称: 4-trimethylsiloxy-4-phenyl-1-butene
• 英文别名: trimethyl((1-phenylbut-3-en-1-yl)oxy)silane；trimethyl[(1-phenyl-3-butenyl)oxy]silane；trimethyl-(1-phenylbut-3-enyloxy)silane；trimethyl(1-phenylbut-3-enyloxy)silane；4-phenyl-4-trimethylsiloxy-1-butene；4-Trimethylsilyloxy-4-phenylbut-1-ene；trimethyl(1-phenylbut-3-enoxy)silane
• CAS: 139284-72-3；69492-27-9
• 化学式: C₁₃H₂₀OSi
• 分子量: 220.387
• InChiKey: BXBAGJFJJLLOFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  255.7±9.0 °C(Predicted)
• 密度：
  0.907±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  三甲基[(1-苯基-3-丁烯基)氧基]硅烷 在 Celite 、 polystyrene-bound super Broensted acid 、 水 作用下， 以 四氢呋喃 为溶剂， 以57 mg的产率得到1-苯基-3-丁烯-1-醇
  参考文献：
  名称：

  Single-Pass Reaction Column System with Super Brønsted Acid-loaded Resin

  摘要：

  多种酸催化的反应只需将反应物溶液通过装填有聚苯乙烯结合的超强布朗斯台德酸（1）的反应柱一次，即可高产率地得到所需产物。极性和非极性有机溶剂可溶胀的（1）相较于填充在柱中的磺化聚合物Nafion® SAC-13（2）作为载有布朗斯台德酸的树脂，性能优越得多。

  DOI：

  10.1055/s-2002-32964
• 作为产物：
  描述：

  1-苯基-3-丁烯-1-醇 、 六甲基二硅氮烷 在 碘 作用下， 反应 0.25h， 以76%的产率得到三甲基[(1-苯基-3-丁烯基)氧基]硅烷
  参考文献：
  名称：

  Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)

  摘要：

  An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol%) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.040

文献信息

• Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki–Hiyama–Kishi allylation of benzaldehyde
  作者：Gráinne C. Hargaden、Timothy P. O'Sullivan、Patrick J. Guiry

  DOI：10.1039/b715834c

  日期：——

  good to high-yielding three-step synthesis of non-symmetrical bis(oxazoline)-containing ligands possessing an N-thienylaniline unit. The convergent synthesis employed a palladium-catalysed aryl amination of 2-(2'-bromothiophene)nitrile as the key step, with sixteen ligands prepared in total. These ligands were subsequently applied in the chromium-catalysed enantioselective Nozaki-Hiyama-Kishi allylation

  我们报告了具有N-噻吩基苯胺单元的非对称双（恶唑啉）含配体的高产三步合成的好。收敛合成采用2-（2'-溴噻吩）腈的钯催化芳基胺化作为关键步骤，总共制备了十六个配体。随后将这些配体以73％的最佳对映选择性应用于苯甲醛的铬催化的对映选择性Nozaki-Hiyama-Kishi烯丙基化反应中。
• Chemoselective Nucleophilic Functionalizations of Aromatic Aldehydes and Acetals via Pyridinium Salt Intermediates
  作者：Takahiro Kawajiri、Maho Kato、Hiroki Nakata、Ryota Goto、Shin-yo Aibara、Reiya Ohta、Hiromichi Fujioka、Hironao Sajiki、Yoshinari Sawama

  DOI：10.1021/acs.joc.8b02965

  日期：2019.4.5

  synthesizing the target molecules. The perfect chemoselectivity between aromatic and aliphatic aldehydes is difficult to achieve by the previous methods. The aromatic aldehyde-selective nucleophilic addition in the presence of aliphatic aldehydes was newly accomplished. Namely, the aromatic aldehyde-selective nucleophilic addition using arenes and allyl silanes proceeded in the presence of trialkylsilyl

  新型化学选择性功能化的发展可以使合成靶分子的策略多样化。用以前的方法很难达到芳族和脂族醛之间的完美化学选择性。新近完成了在脂肪族醛存在下的芳香族醛选择性亲核加成反应。即，使用芳烃和烯丙基硅烷的芳族醛选择性亲核加成在三烷基甲硅烷基三氟甲磺酸酯和2,2'-联吡啶基的存在下进行，而脂族醛完全保持不变。衍生自芳族醛的反应性吡啶鎓盐类中间体经过化学选择性亲核取代。而且，作为保护醛的芳香族缩醛可以直接转化为类似的吡啶鎓盐中间体，
• Cationic Cobalt Porphyrin-Catalyzed Allylation of Aldehydes with Allyltrimethylsilanes
  作者：Rei Tomifuji、Shota Masuda、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/acs.orglett.9b01303

  日期：2019.5.17

  porphyrin-catalyzed allylation of aldehydes with allyltrimethylsilanes is developed. The formation of the aldehyde–cobalt porphyrin complex, the key intermediate for the addition of allylsilanes, is confirmed by theoretical studies and synchrotron-based X-ray absorption fine-structure measurements. Facile dissociation of the product by allylation from the cobalt complex regenerates the active complex with

  开发了阳离子钴卟啉催化的醛与烯丙基三甲基硅烷的烯丙基化反应。理论研究和基于同步加速器的X射线吸收精细结构测量结果证实了醛-钴卟啉配合物（添加烯丙基硅烷的关键中间体）的形成。通过烯丙基化从钴络合物中使产物容易解离，使活性络合物与醛再生。容易获得的[Co（TPP）] SbF 6络合物可作为该烯丙基化的有效催化剂。
• Crucial role of the ligand of silyl Lewis acid in the Mukaiyama aldol reactionElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b2/b203838b/
  作者：Kazuaki Ishihara、Yukihiro Hiraiwa、Hisashi Yamamoto

  DOI：10.1039/b203838b

  日期：2002.7.11

  The Me3SiX-induced Mukaiyama aldol reaction proceeds through each catalytic cycle under the influence of X-: the silyl group of Me3SiNTf2 does not release from -NTf2 and that of silyl enol ether intermolecularly transfers to the product, while the silyl group of Me3SiOTf remains in the product and that of the silyl enol ether becomes the catalyst for the next catalytic cycle.

  Me3SiX诱导的Mukaiyama羟醛反应在X-的影响下在每个催化循环中进行：Me3SiNTf2的甲硅烷基不会从-NTf2释放，甲硅烷基烯醇醚的分子间转移到产物中，而Me3SiOTf的甲硅烷基仍保留在产物和甲硅烷基烯醇醚的产物成为下一催化循环的催化剂。
• Iron(III) chloride-catalyzed effective allylation reactions of aldehydes with allyltrimethylsilane
  作者：Tsutomu Watahiki、Takeshi Oriyama

  DOI：10.1016/s0040-4039(02)02107-x

  日期：2002.12

  Iron(III) chloride-catalyzed allylation reactions of a variety of aldehydes with allyltrimethylsilane proceeded efficiently and smoothly to afford the corresponding homoallyl alcohols in high to excellent yields. This novel method could be suitable especially for the allylation of sterically hindered aliphatic aldehydes.

  多种醛与烯丙基三甲基硅烷的氯化铁催化的烯丙基化反应可高效，平稳地进行，从而以高收率或优异的收率得到相应的均烯丙基醇。该新方法可能特别适合于空间受阻的脂族醛的烯丙基化。