1-iodo-10-undecene | 7766-49-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1-iodo-10-undecene
• 英文别名: 11-iodoundec-1-ene
• CAS: 7766-49-6
• 化学式: C₁₁H₂₁I
• 分子量: 280.192
• InChiKey: YYNLZUIWHBPGGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  12
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-iodo-10-undecene 在 lithium aluminium tetrahydride 、 氯化亚砜 、 双氧水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲基叔丁基醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.17h， 生成 N-(4-(dodecyloxy)-3,5-bis((11-hydroxyundecyl)oxy)benzyl)-N,N-diethylethanaminium chloride
  参考文献：
  名称：

  3D Interconnected Ionic Nano-Channels Formed in Polymer Films: Self-Organization and Polymerization of Thermotropic Bicontinuous Cubic Liquid Crystals

  摘要：

  Thermotropic bicontinuous cubic (Cub(bi)) liquid-crystalline (LC) compounds based on a polymerizable ammonium moiety complexed with a lithium salt have been designed to obtain lithium ion-conductive all solid polymeric films having 3D interconnected ionic channels. The monomer shows a Cub(bi) phase from -5 to 19 degrees C on heating. The complexes retain the ability to form the Cub(bi) LC phase. They also form hexagonal columnar (Col(h)) LC phases at temperatures higher than those of the Cub(bi) phases. The complex of the monomer and LiBF4 at the molar ratio of 4: 1 exhibits the Cub(bi) and Col(h) phases between -6 to 19 degrees C and 19 to 56 degrees C, respectively, on heating. The Cub(bi) LC structure formed by the complex has been successfully preserved by in situ photopolymerization through UV irradiation in the presence of a photoinitiator. The resultant nanostructured film is optically transparent and free-standing. The X-ray analysis of the film confirms the preservation of the self-assembled nanostructure. The polymer film with the Cub(bi) LC nanostructure exhibits higher ionic conductivities than the polymer films obtained by photopolymerization of the complex in the Col(h) and isotropic phases. It is found that the 3D interconnected ionic channels derived from the Cub(bi) phase function as efficient ion-conductive pathways.

  DOI：

  10.1021/ja106707z
• 作为产物：
  描述：

  10-十一烯-1-醇 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 1-iodo-10-undecene
  参考文献：
  名称：

  在Au表面上具有自组装的功能化β-环糊精单分子层的对映体的手性鉴别

  摘要：

  设计了一条容易的合成巯基官能化的β-环糊精的合成路线，并将其自行组装到石英晶体微量天平（QCM）的金电极上，以提供一种能够对映异构体进行手性鉴别的耐用传感器。

  DOI：

  10.1016/s0040-4039(02)00267-8

文献信息

• Silver-Catalyzed Trifluoromethoxylation of Alkyl Trifluoroborates
  作者：Xiaohuan Jiang、Pingping Tang

  DOI：10.1021/acs.orglett.0c01741

  日期：2020.7.2

  A silver-catalyzed trifluoromethoxylation of alkyl trifluoroborates with trifluoromethyl arylsulfonate as the trifluoromethoxylation reagent has been reported for the first time. This reaction is performed under mild reaction conditions and has wide functional group compatibility. In addition, the mechanism of this site-specific trifluoromethoxylation is proposed as a radical pathway.

  首次报道了用三氟甲基芳基磺酸盐作为三氟甲氧基化试剂的银催化的三氟硼酸烷基酯的三氟甲氧基化。该反应在温和的反应条件下进行，并且具有广泛的官能团相容性。另外，该位点特异性三氟甲氧基化的机制被提议为自由基途径。
• Tsuji-Wacker Oxidation of Terminal Olefins using a Palladium-Carbon Nanotube Nanohybrid
  作者：Simon Donck、Edmond Gravel、Nimesh Shah、Dhanaji V. Jawale、Eric Doris、Irishi N. N. Namboothiri

  DOI：10.1002/cctc.201500241

  日期：2015.8.3

  Palladium nanoparticles supported on carbon nanotubes were used in the Tsuji–Wacker oxidation. The palladium‐based nanohybrid was found to be very active in combination with cuprous chloride for the selective oxidation of terminal olefins into methyl ketones. The co‐catalytic system operates under very mild and sustainable conditions (room temperature, atmospheric pressure, low catalyst loading), as

  碳纳米管上负载的钯纳米颗粒用于Tsuji-Wacker氧化中。人们发现，钯基纳米杂化物与氯化亚铜结合使用对将末端烯烃选择性氧化为甲基酮具有很高的活性。与以前报道的催化剂相比，该助催化系统在非常温和且可持续的条件下（室温，大气压，低催化剂负载）运行，并且可以循环使用而不会损失任何活性。
• The First Conversion of Primary Alkyl Halides to Nitroalkanes under Aqueous Medium
  作者：Roberto Ballini、Luciano Barboni、Guido Giarlo

  DOI：10.1021/jo049048b

  日期：2004.10.1

  obtained in aqueous medium by reaction of the corresponding halo derivatives with silver nitrite. The procedure works well with both alkyl bomide and alkyl iodide and proceeds in satisfactory to good yields even in the presence of other functionalities, minimizing the formation of the undesired alkyl nitrites.

  通过使相应的卤代衍生物与亚硝酸银反应，可以很容易地在水性介质中获得伯硝基烷和α，ω-二硝基烷。该方法对于烷基溴化物和烷基碘化物都很好地工作，并且即使在存在其他官能团的情况下也以令人满意的良好收率进行，从而最小化了不希望的亚硝酸烷基酯的形成。
• Synthesis of a para-quinone macrolactam related to geldanamycin by ring closing metathesis
  作者：Aude Lemarchand、Thorsten Bach

  DOI：10.1016/j.tet.2004.06.147

  日期：2004.10

  macrocyclic 2,5-di-iso-propoxy-4-methoxyanilide 22 was prepared. The iso-propyl protecting groups could be selectively cleaved and the intermediate para-hydroquinone oxidized on air to the desired para-quinone 2 (86% yield). The compound shows some key features (macrolactam ring with the same ring size, α,β,γ,δ-unsaturated anilide, para-quinone) of geldanamycin.

  用α，β，γ，δ-不饱和3-烯基-2,4,5-三甲氧基苯胺11进行的模型研究表明，如果ansa链包含14个以上的原子，则这些化合物的闭环易位（RCM）是可能的。（Z）构型的产物12c – e以良好的收率（77–87％）和完美的简单非对映选择性获得。由于2,4,5-三甲氧基苯胺的氧化主要导致不期望的邻醌，例如15或对-氮杂醌，例如16，因此制备了大环2,5-二-异-异丙氧基-4-甲氧基苯胺22。该异可以选择性地裂解-丙基保护基，并将中间的对-对苯二酚在空气中氧化为所需的对-对苯二酚2（86％收率）。该化合物显示了格尔德霉素的一些关键特征（具有相同环大小的半内酰胺环，α，β，γ，δ-不饱和苯胺，对醌）。
• Difluoromethylation of Alkyl Bromides and Iodides with TMSCF₂H
  作者：Haiwei Zhao、Changhui Lu、Simon Herbert、Wei Zhang、Qilong Shen

  DOI：10.1021/acs.joc.0c02783

  日期：2021.2.5

  of unactivated alkyl bromides and iodides. Reactions of alkyl iodides with TMSCF2H were mediated by a copper catalyst using CsF as the activator, while reactions of less reactive alkyl bromides required a combination of palladium and a stoichiometric amount of CuI as the catalysts. Preliminary mechanistic studies of the synergistic Pd/Cu-catalyzed difluoromethylation of alkyl bromides suggest that it

  我们首次描述了两种用于未活化的烷基溴和碘的直接二氟甲基化的方案。烷基碘与TMSCF 2 H的反应由使用CsF作为活化剂的铜催化剂介导，而反应性较低的烷基溴的反应需要钯和化学计量的CuI的组合。对Pd / Cu催化的烷基溴的二氟甲基化协同作用的初步机理研究表明，它可能通过Pd（I）/ Pd（III）催化循环进行。