(methoxymethylene)cycloheptane | 66051-09-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (methoxymethylene)cycloheptane
• 英文别名: (Methoxymethylidene)cycloheptane；methoxymethylidenecycloheptane
• CAS: 66051-09-0
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: KKFRZZMWMFYFPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (methoxymethylene)cycloheptane 生成 1-cycloheptene-1-carboxaldehyde
  参考文献：
  名称：

  A Novel Synthesis of α,β-Unsaturated Aldehydes and Esters by Dye-Photooxygenation of Methyl Enol Ethers

  摘要：

  DOI：

  10.1055/s-1978-24681
• 作为产物：
  描述：

  (methoxymethylene)triphenylphosphorane 、 环庚酮 生成 (methoxymethylene)cycloheptane
  参考文献：
  名称：

  A Novel Synthesis of α,β-Unsaturated Aldehydes and Esters by Dye-Photooxygenation of Methyl Enol Ethers

  摘要：

  DOI：

  10.1055/s-1978-24681

文献信息

• Nickel catalyzed dealkoxylative C_sp2–C_sp3 cross coupling reactions – stereospecific synthesis of allylsilanes from enol ethers
  作者：Lin Guo、Matthias Leiendecker、Chien-Chi Hsiao、Christoph Baumann、Magnus Rueping

  DOI：10.1039/c4cc08187k

  日期：——

  The application of cyclic and acyclic enol ethers as electrophiles in cross coupling reactions offers new possibilities for the preparation of functional compounds.

  环状和非环状烯醇醚作为亲电试剂在交叉偶联反应中的应用为功能化合物的制备提供了新的可能性。
• Direct α-Benzylation of Methyl Enol Ethers with Activated Benzyl Alcohols: Its Rearrangement and Access to (±)-Tetrahydronyasol, Propterol A, and 1,3-Diarylpropane
  作者：Tapan Kumar Jena、Faiz Ahmed Khan

  DOI：10.1021/acs.joc.9b02064

  日期：2019.11.1

  Herein, we report a one-pot Lewis acid mediated synthesis of bi- and triarylpropanal derivatives and their corresponding isomeric ketones from aromatic enol ethers. This transformation takes place via nucleophilic attack of enol ethers to electron-rich benzyl alcohols. The substrate scope of this indicates that it might proceed via quinomethoxy methide as a key intermediate leading to propanal derivatives

  在本文中，我们报道了一锅路易斯酸介导的从芳族烯醇醚合成的二芳基和三芳基丙醛衍生物及其相应的异构酮的合成。这种转化是通过烯醇醚向富电子的苄醇的亲核攻击而发生的。该物质的底物范围表明它可能通过喹甲氧基甲基化物作为导致丙醛衍生物的关键中间体进行，并且它们的Wagner-Meerwein重排提供了异构体酮。此外，该方法学适用于（±）-四氢nyasol，丙醇A和1,3-二芳基丙烷的合成。
• Acid mediated synthesis of thiazolines, thiazoles and enamide derivatives from methyl enol ethers: Application towards synthesis of wilsoniamine B
  作者：Tapan Kumar Jena、Faiz Ahmed Khan

  DOI：10.1016/j.tetlet.2020.151675

  日期：2020.3

  metal-free synthesis of thiazolines, dihydrothiazole and enureas or thioureas from methyl enol ether with urea or thiourea derivatives in the presence of TFA (trifluoroacetic acid) are reported here. This synthetic protocol involves the formation of two bonds, C-N as well as C-S, in one step for the synthesis of thiazoline derivatives, dihydrothiazoles and a direct C-N bond for the synthesis of enamides

  本文报道了在TFA（三氟乙酸）存在下，由甲基烯醇醚与尿素或硫脲衍生物有效地无金属合成噻唑啉，二氢噻唑和脲或硫脲。该合成方案涉及在一步合成噻唑啉衍生物，二氢噻唑和直接CN键的两个步骤，即CN和CS的形成，从而以良好或优异的产率合成烯酰胺。此外，该方法用于合成wilsoniamine B生物碱。
• Combined C–H Functionalization/Cope Rearrangement with Vinyl Ethers as a Surrogate for the Vinylogous Mukaiyama Aldol Reaction
  作者：Yajing Lian、Huw M. L. Davies

  DOI：10.1021/ja2051155

  日期：2011.8.10

  selectively undergo the combined C-H functionalization/Cope rearrangement reaction via an s-cis/boat transition state. With chiral dirhodium catalysts, products are generated in a highly diastereoselective and enantioselective fashion. This reaction can be considered as a surrogate to the traditional vinylogous Mukaiyama aldol reaction. Effective kinetic resolution has been achieved, leading to the recovery

  乙烯基醚通过顺式/船过渡态选择性地进行组合的 CH 官能化/Cope 重排反应。使用手性铑催化剂，产品以高度非对映选择性和对映选择性方式生成。这种反应可以被认为是传统乙烯基向山醛醇反应的替代物。已实现有效的动力学拆分，导致回收具有高对映体纯度的轴向手性的环状乙烯基醚。
• A radical cyclisation strategy to α-spiro-β-methylene-γ-butyrolactones. Total synthesis of (±)-norbakkenolide-A
  作者：Adusumilli Srikrishna、Sankuratri Nagaraju、G. Veera Raghava Sharma

  DOI：10.1039/c39930000285

  日期：——

  The 5-exo-dig radical cyclisation reaction of the bromoacetals 9, obtained from the enol ethers 8, and treatment of the resulting hemiacetal 10 with Jones′ reagent transforms the cyclic ketones 7 and 12 into α-spiro-β-methylene-γ-butyrolactones 11 and norbakkenolide-A 2.

  通过烯醇醚 8 得到的溴乙醛 9 的 5-exo-dig 自由基环化反应，以及用 Jonesâ² 试剂处理得到的半缩醛 10，可将环状酮 7 和 12 转化为 δ-螺δ-亚甲基δ-丁内酯 11 和去甲斑蝥内酯-A 2。