triethyl(pent-4-en-1-yloxy)silane | 374755-00-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: triethyl(pent-4-en-1-yloxy)silane
• 英文别名: 5-(triethylsiloxy)pent-1-ene；4-pentenoxytriethylsilane；Triethyl(pent-4-enoxy)silane
• CAS: 374755-00-7
• 化学式: C₁₁H₂₄OSi
• 分子量: 200.396
• InChiKey: NIHFLQKZWPOGCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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(pent-4-en-1-yloxy)silane 在 palladium diacetate potassium phosphate 、 三环己基膦 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 13-chloro-1-(triethylsiloxy)tridecane
  参考文献：
  名称：

  具有β氢的烷基溴的室温烷基-烷基铃木交叉偶联。

  摘要：

  DOI：

  10.1021/ja011306o
• 作为产物：
  描述：

  4-戊烯-1-醇 、 三乙基氯硅烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到triethyl(pent-4-en-1-yloxy)silane
  参考文献：
  名称：

  Synthesis and conformational analysis of novel water soluble macrocycles incorporating carbohydrates, including a β-cyclodextrin mimic

  摘要：

  Rigid macrocyclic scaffolds based on carbohydrates have potential for the display of recognition groups with defined 3D structure and may have application in bioorganic and supramolecular chemistry. A series of water soluble macrocyclic structures containing two saccharide units was synthesised by ring closing metathesis of allyl and pentenyl glycosides derived from glucuronic acid. The 3D structure of the constrained systems was explored by NMR and computational methods. CD spectra were also recorded. On the basis of experimental observations we suggest that the carbohydrate presentation is constrained into a U-shape for the smaller ring size but can access an S-shape arrangement in the larger macrocycle. As an extension it is shown that the larger macrocycle displayed phenomena similar to beta-cyclodextrin (beta-CD). The binding of 8-anilino-1-naphthalenesulfonate (ANS) to beta-CD is detectable by reversal of quenching of the ANS emission spectrum and a similar reversal of quenching was observed when this macrocycle was added to a solution of ANS; this was further supported by NMR. Furthermore molecular modelling suggests that the macrocyclic scaffolding has potential for the development of peptidomimetics. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.020

文献信息

• Palladium-Catalyzed Oxidative Amination of Alkenes:  Improved Catalyst Reoxidation Enables the Use of Alkene as the Limiting Reagent
  作者：Michelle M. Rogers、Vasily Kotov、Jaruwan Chatwichien、Shannon S. Stahl

  DOI：10.1021/ol701903r

  日期：2007.10.1

  Palladium-catalyzed methods for intermolecular aerobic oxidative amination of alkenes have been identified that are compatible with the use of alkene as the limiting reagent. These procedures, which enhance the utility of this reaction with alkenes that are not commercially available, are demonstrated with substrates bearing dialkyl ether, carboxyester, epoxide, and silyl ether groups.

  已经鉴定出钯催化的用于烯烃的分子间需氧氧化胺化的方法与使用烯烃作为限制试剂是相容的。用带有二烷基醚，羧酸酯，环氧化物和甲硅烷基醚基团的底物证明了这些提高与没有市售烯烃的反应的实用性的方法。
• Palladium catalysed cross-coupling of vinyl triflates with 9-alkyl-9-borobicyclo[3,3,1]nonanes. total synthesis of (−)-Isoseiridine.
  作者：Ronald Grigg、Peter Kennewell、Vladimir Savic

  DOI：10.1016/s0040-4020(01)80703-1

  日期：1994.5

  Catalysed cross-coupling of butenolide-3-triflates to 9-alkyl-9-borobicyclo[3.3.1]nonanes occurs in moderate to good yield and tolerates a range of functionality. Application of this methodology combined with addition of diethylzinc to a butenolide aldehyde in the presence of an ephedrine derivative leads to a 3-step synthesis of (−)-isoseiridine with 88%e.e. in good yield.

  Pd（O）催化的丁烯内酯-3-三氟甲磺酸酯到9-烷基-9-硼双环[3.3.1]壬烷的交叉偶联反应具有中等至良好的收率，并具有一定的功能范围。该方法的应用与在麻黄碱衍生物存在下将二乙基锌加到丁烯醛中的方法相结合，可实现收率达88％ee的（-）-异水苏啶的3步合成。
• Branch-Selective Allylic C–H Carboxylation of Terminal Alkenes by Pd/sox Catalyst
  作者：Hiroki Kondo、Feng Yu、Junichiro Yamaguchi、Guosheng Liu、Kenichiro Itami

  DOI：10.1021/ol5019135

  日期：2014.8.15

  A ligand-controlled branch-selective allylic C-H carboxylation through Pd catalysis is described. The developed catalytic system, which consists of Pd(OAc)(2), sulfoxide oxazoline (sox) as a ligand and benzoquinone as an oxidant, couples terminal alkenes and carboxylic acids to furnish the corresponding branched allylic esters with high regioselectivity.
• Room-Temperature Alkyl−Alkyl Suzuki Cross-Coupling of Alkyl Bromides that Possess β Hydrogens
  作者：Matthew R. Netherton、Chaoyang Dai、Klaus Neuschütz、Gregory C. Fu

  DOI：10.1021/ja011306o

  日期：2001.10.1
• Synthesis and conformational analysis of novel water soluble macrocycles incorporating carbohydrates, including a β-cyclodextrin mimic
  作者：Trinidad Velasco-Torrijos、Paul V. Murphy

  DOI：10.1016/j.tetasy.2004.11.020

  日期：2005.1

  Rigid macrocyclic scaffolds based on carbohydrates have potential for the display of recognition groups with defined 3D structure and may have application in bioorganic and supramolecular chemistry. A series of water soluble macrocyclic structures containing two saccharide units was synthesised by ring closing metathesis of allyl and pentenyl glycosides derived from glucuronic acid. The 3D structure of the constrained systems was explored by NMR and computational methods. CD spectra were also recorded. On the basis of experimental observations we suggest that the carbohydrate presentation is constrained into a U-shape for the smaller ring size but can access an S-shape arrangement in the larger macrocycle. As an extension it is shown that the larger macrocycle displayed phenomena similar to beta-cyclodextrin (beta-CD). The binding of 8-anilino-1-naphthalenesulfonate (ANS) to beta-CD is detectable by reversal of quenching of the ANS emission spectrum and a similar reversal of quenching was observed when this macrocycle was added to a solution of ANS; this was further supported by NMR. Furthermore molecular modelling suggests that the macrocyclic scaffolding has potential for the development of peptidomimetics. (C) 2004 Elsevier Ltd. All rights reserved.