(4-pentenyloxy)trimethylsilane | 14031-96-0

• 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: (4-pentenyloxy)trimethylsilane
• 英文别名: Silane, trimethyl(4-pentenyloxy)-；trimethyl(pent-4-enoxy)silane
• CAS: 14031-96-0
• 化学式: C₈H₁₈OSi
• mdl: MFCD11553873
• 分子量: 158.316
• InChiKey: XGPXKYJNRNGJPY-UHFFFAOYSA-N

物化性质

• 沸点：
  40-42 °C(Press: 22 Torr)
• 密度：
  0.800±0.06 g/cm3(Predicted)
• 保留指数：
  880.5

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (4-pentenyloxy)trimethylsilane 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以91%的产率得到2-甲基四氢呋喃
  参考文献：
  名称：

  Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane–Iodine Catalytic System

  摘要：

  A novel catalytic system using I-2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.

  DOI：

  10.1021/acs.orglett.5b01797
• 作为产物：
  描述：

  四氢糠醇 在 fused reduced iron catalyst 氢气 作用下， 250.0~300.0 ℃ 、2.0 MPa 条件下， 生成 (4-pentenyloxy)trimethylsilane
  参考文献：
  名称：

  Reaction of tetrahydrofurfuryl alcohol with dimethylamine and/or hydrogen

  摘要：

  DOI：

  10.1007/bf00957256

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。
• Synthesis of trimethylsilyloxy and hydroxy compounds from carbanions and bis (trimethylsilyl)peroxide
  作者：Lucia Camici、Pasquale Dembech、Alfredo Ricci、Giancarlo Seconi、Maurizio Taddei

  DOI：10.1016/s0040-4020(01)86666-7

  日期：1988.1

  The reactions of bis (trimethylsilyl) peroxide with alkyl, vinyl, alkynyl, aromatic and heteroaromatic anions are described. Depending on the reaction conditions, the trimethylsilyloxy derivatives can be obtained alone or together with the corresponding trimethylsilyl derivatives, which is sometimes the major product. Enolates, generated using magnesium diisopropylamide give the corresponding hydroxycarbonyl

  描述了双（三甲基甲硅烷基）过氧化物与烷基，乙烯基，炔基，芳族和杂芳族阴离子的反应。取决于反应条件，三甲基甲硅烷基氧基衍生物可以单独获得或与相应的三甲基甲硅烷基衍生物一起获得，其有时是主要产物。使用二异丙基酰胺镁生成的烯醇化物以良好的收率得到相应的羟基羰基化合物。给出合理化上述结果的尝试，强调了双（三甲基甲硅烷基）过氧化物在有机合成中作为亲电子羟基化试剂的广泛应用。
• Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis
  作者：Xinxin He、Xinyan Wang、Ying-Lung Steve Tse、Zhihai Ke、Ying-Yeung Yeung

  DOI：10.1021/acscatal.1c03622

  日期：2021.10.15

  Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in

  路易斯酸经常用于催化，但它们通常具有高湿度敏感性。在许多反应中，由于强路易斯酸也与产物结合的问题，催化剂会失活。在这项研究中，已经开发了源自​​硒双阳离子中心的水解稳定的双齿路易斯酸催化剂。双硒催化剂用于在各种转化中以良好的收率和选择性活化亚胺和羰基。发现双硒鎓盐的路易斯酸度比单硒鎓体系强，这归因于两个阳离子硒鎓中心的协同作用。此外，双硒催化剂不受强碱或水分的抑制。
• Applications of Selenonium Cations as Lewis Acids in Organocatalytic Reactions
  作者：Xinxin He、Xinyan Wang、Ying-Lung Steve Tse、Zhihai Ke、Ying-Yeung Yeung

  DOI：10.1002/anie.201806965

  日期：2018.9.24

  The use of trisubstituted selenonium salts as organic Lewis acids in electrophilic halogenation and aldol‐type reactions has been developed. The substrate scope is broad. The reaction conditions are mild and compatible with various functionalities. This study opens a new avenue for the development of nonmetallic Lewis acid catalysis.

  在亲电子卤化和醛醇型反应中，已经开发了将三取代硒鎓盐用作有机路易斯酸的方法。基材范围很广。反应条件温和并且与各种功能相容。这项研究为非金属路易斯酸催化的发展开辟了一条新途径。
• A facile stereoselective route to a C/D-ring synthon for 20-epi-22-oxavitamin D3 analogues
  作者：Susumi Hatakeyama、Tatsuhiko Ikeda、Hiroshi Irie、Chino Izumi、Hisato Mori、Kohsei Uenoyama、Hidetoshi Yamada、Mugio Nishizawa

  DOI：10.1039/c39950001959

  日期：——

  An efficient method for the preparation of a C/D-ring synthon for 20-epi-22-oxavitamin D3 analogues is developed based on Me3SiOSO2CF3 catalysed reductive etherification of a ketone with an alkoxytrimethylsilane in the presence of triethylsilane.

  在三乙基硅烷存在下，基于Me 3 SiOSO 2 CF 3催化的酮与烷氧基三甲基硅烷的还原性醚化作用，开发了一种有效的方法来制备20-表-22-恶维他命D 3类似物的C / D环合成子。