11-(tert-butyldiphenylsilyloxy)-1-undecene

• 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: 11-(tert-butyldiphenylsilyloxy)-1-undecene
• 英文别名: tert-butyl(diphenyl)(undec-10-enyloxy)silane；tert-butyldiphenyl(undec-10-en-1-yloxy)silane；11-[((1,1-dimethylethyl)diphenylsilicon)oxy]-1-undecene；tert-butyl(diphenyl)(undec-10-enyloxy)-L-proline；Tert-butyl-diphenyl-undec-10-enoxysilane
• 化学式: C₂₇H₄₀OSi
• 分子量: 408.7
• InChiKey: DJKHLSRKTKUXMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  11-(tert-butyldiphenylsilyloxy)-1-undecene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 以98%的产率得到
  参考文献：
  名称：

  Catalysis via Homolytic Substitutions with C−O and Ti−O Bonds: Oxidative Additions and Reductive Eliminations in Single Electron Steps

  摘要：

  In a combined theoretical and experimental study, an efficient catalytic reaction featuring epoxide opening and tetrahydrofuran formation through homolytic substitution reactions at C-O and Ti-O bonds was devised. The performance of these two key steps of the catalytic cycle was studied and could be adjusted by modifying the electronic properties of the catalysts through introduction of electron-donating or -withdrawing substituents to the titanocene catalysts. By regarding both steps as single electron versions of oxidative addition and reductive elimination, a mechanism-based platform for the design of catalysts and reagents-for electron transfer reactions evolved that opens broad perspectives for further investigations.

  DOI：

  10.1021/ja907817y
• 作为产物：
  描述：

  10-十一烯-1-醇 、 叔丁基二苯基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 11-(tert-butyldiphenylsilyloxy)-1-undecene
  参考文献：
  名称：

  A Concise Diastereoselective Approach to the Left-Hand Side of Batzelladine A

  摘要：

  该反应的立体选择性以及本文中描述的相关观察结果，使我们对该反应的机理有了更深入的了解。

  DOI：

  10.1055/s-2008-1077969

文献信息

• Straightforward Synthesis of α-Substituted Prolines by Cross-Metathesis
  作者：Marco Lumini、Franca M. Cordero、Federica Pisaneschi、Alberto Brandi

  DOI：10.1002/ejoc.200800044

  日期：2008.6

  The synthesis of several α-substituted N-Boc-protected prolines has been achieved by cross metathesis (CM) of N-Boc-allylproline 5 with terminal long chain alkenes and alkenes bearing hydroxy, silyloxy, ester, and O-acetylglucosamido groups. The CM occurred with good selectivity and short reaction time under microwave heating conditions, affording yields in the range of 40–92 %. Addition of Ti(OiPr)4

  通过 N-Boc-烯丙基脯氨酸 5 与末端长链烯烃和带有羟基、甲硅烷氧基、酯和 O-乙酰氨基葡糖基团的烯烃的交叉复分解 (CM)，合成了几种 α-取代的 N-Boc 保护的脯氨酸。在微波加热条件下，CM 具有良好的选择性和较短的反应时间，产率范围为 40-92%。在具有路易斯碱性取代基的烯烃的情况下，添加作为路易斯酸的 Ti(OiPr) 4 允许略微增加产率。CM 也成功地应用于用三氯乙醛 4 保护的烯丙基脯氨酸，但中间产物对于进一步脱保护和加工不太实用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Photoinduced, copper-catalyzed three components cyanofluoroalkylation of alkenes with fluoroalkyl iodides as fluoroalkylation reagents
  作者：Quanping Guo、Mengran Wang、Yanfang Wang、Zhaoqing Xu、Rui Wang

  DOI：10.1039/c7cc07128k

  日期：——

  In the past few years, Ru and Ir catalyzed photoredox radical coupling reactions have been widely applied in organic synthesis. In contrast, the applications of Cu catalysts in photoredox organic transformations were limited. We here report the first example of photoinduced, Cu-catalyzed three component cyanofluoroalkylation of alkenes by directly using fluoroalkyl iodides as fluoroalkylation reagents

  近年来，Ru和Ir催化的光氧化还原自由基偶联反应已广泛应用于有机合成中。相反，Cu催化剂在光氧化还原有机转化中的应用受到限制。我们在此报告通过直接使用氟代烷基碘化物作为氟代烷基化试剂，进行光诱导的，铜催化的烯烃三组分氰基氟代烷基化的第一个例子。
• Site-Selective Catalytic Carboxylation of Unsaturated Hydrocarbons with CO₂ and Water
  作者：Morgane Gaydou、Toni Moragas、Francisco Juliá-Hernández、Ruben Martin

  DOI：10.1021/jacs.7b07637

  日期：2017.9.6

  A catalytic protocol that reliably predicts and controls the site-selective incorporation of CO2 to a wide range of unsaturated hydrocarbons utilizing water as formal hydride source is described. This platform unlocks an opportunity to catalytically repurpose three abundant, orthogonal feedstocks under mild conditions.

  描述了一种催化协议，该协议利用水作为正式氢化物源可靠地预测和控制 CO2 的位点选择性掺入到各种不饱和烃中。该平台为在温和条件下催化重新利用三种丰富的正交原料提供了机会。
• Pd-Catalyzed Highly Chemo- and Regioselective Hydrocarboxylation of Terminal Alkyl Olefins with Formic Acid
  作者：Wenlong Ren、Jianxiao Chu、Fei Sun、Yian Shi

  DOI：10.1021/acs.orglett.9b02101

  日期：2019.8.2

  An efficient Pd-catalyzed hydrocarboxylation of alkenes with HCOOH is described. A wide variety of linear carboxylic acids bearing various functional groups can be obtained with excellent chemo- and regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO.

  描述了用HCOOH有效地Pd催化的烯烃加氢羧化反应。在温和的反应条件下，可以得到具有优异的化学和区域选择性的各种带有各种官能团的线性羧酸。反应过程操作简单，不需要处理有毒的CO。
• A Pd-Catalyzed Site-Controlled Isomerization of Terminal Olefins
  作者：Wenlong Ren、Fei Sun、Jianxiao Chu、Yian Shi

  DOI：10.1021/acs.orglett.0c00168

  日期：2020.3.6

  An effective Pd-catalyzed isomerization of olefins with 2-PyPPh2 as the ligand is described. A wide variety of trans-2-olefins bearing various functional groups can be obtained with high regio- and stereoselectivity under mild reaction conditions. The ligand is crucial for the reaction.

  描述了以2-PyPPh2作为配体的烯烃的有效Pd催化异构化。在温和的反应条件下，可以以高区域选择性和立体选择性获得具有各种官能团的各种反式-2-烯烃。配体对于反应至关重要。