trans-1,2-epoxy-3-undecene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: trans-1,2-epoxy-3-undecene
• 英文别名: 2-[(E)-non-1-enyl]oxirane
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: ODCKDGKOYGKLQJ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-1,2-epoxy-3-undecene 在 bis(1,1,1-trifluoroacetylacetonato)copper(II) 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以86%的产率得到2-庚基-2,5-二氢呋喃
  参考文献：
  名称：

  WO2007/108999

  摘要：

  公开号：
• 作为产物：
  描述：

  反式-2-癸烯醛 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 0.37h， 生成 trans-1,2-epoxy-3-undecene
  参考文献：
  名称：

  Mild stereoselective formation of tri- and tetrasubstituted olefins by regioselective ring opening of 1,1-disubstituted vinyl oxiranes with dialkyl dithiophosphates

  摘要：

  Presented in this Letter is a mild new method to stereoselectively ring open 1,1-disubstituted vinyl oxiranes using dialkyl dithiophosphate nucleophiles. This new reaction proceeds in toluene at room temperature to afford tri- and tetrasubstituted allylic alcohols with high Z-selectivity. The syn relationship between the alcohol and the newly incorporated dithiophosphate moiety presented an opportunity to evaluate the anionic hopping properties of the ring opening product. Treatment of the ring opening product with base results in a facile phosphate hopping followed by a selective thiolate 3-exo-trig instead of a 5-exo-tet cyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.028

文献信息

• Synthesis of Vinyl Cyclopropanes via Anion Relay Cyclization
  作者：Kevin M. Allegre、Nathan Brennan、Jon A. Tunge

  DOI：10.1021/acs.orglett.8b01566

  日期：2018.7.20

  A method where an allyl alcohol is formed from a Tsuji–Trost allylation between a vinyl epoxide and an acyl containing nucleophile is described. Subsequently, a retro-Claisen condensation is utilized as a means of through-space anion relay. The anion relay results in the formation of a reactive carbanion and simultaneously activates an allylic alcohol toward intramolecular Tsuji–Trost cyclopropanation

  描述了一种方法，其中烯丙基醇由乙烯基环氧化物和含酰基亲核试剂之间的Tsuji-Trost烯丙基化反应形成。随后，逆向克莱森缩合被用作通过空间阴离子中继的手段。阴离子中继导致反应性碳负离子的形成，并同时使烯丙基醇向分子内Tsuji-Trost环丙烷化。因此，在一个锅中，使用温和且操作简单的程序，将Tsuji-Trost烯丙基化，retro-Claisen活化和Tsuji-Trost环丙烷化相结合，可从环氧乙烷中获得合成有用的乙烯基环丙烷。
• Production of 2,5-Dihydrofurans and Analogous Compounds
  申请人：Njardarson Jon

  公开号：US20090131691A1

  公开（公告）日：2009-05-21

  Vinyl oxiranes are rearranged to 2,5-dihydrofuran using catalyst (III) or (IV). The 2,5-dihydrofuran can be reduced to tetrahydrofuran. 3,4-Epoxy-1-butene substrate is converted to 2,5-dihydrofuran which in turn is converted to tetrahydrofuran. Substrate for making 3-methyltetrahydrofuran is prepared from isoprene. Substrate for making 2-methyltetrahydrofuran is prepared from piperylene. Reactions analogous to that with vinyl oxiranes are carried out with vinyl thiiranes and vinyl aziridines.

  乙烯基环氧烷通过催化剂（III）或（IV）重排成2,5-二氢呋喃。2,5-二氢呋喃可以还原成四氢呋喃。3,4-环氧-1-丁烯底物被转化为2,5-二氢呋喃，然后转化为四氢呋喃。制备3-甲基四氢呋喃的底物来自异戊二烯。制备2-甲基四氢呋喃的底物来自戊二烯。与乙烯基环氧硫烷和乙烯基氮杂环丙烷类似的反应也可以进行。
• A Palladium‐Catalyzed Regioselective [3+2] Annulation Strategy to 1,2,3‐Oxathiazolidine‐2‐oxides
  作者：Qian Liang、Ganggang Bu、Hongjian Jiao、Bing Gao

  DOI：10.1002/ejoc.202301153

  日期：2024.3.25

  Palladium-catalyzed [3+2] annulation of N-sulfinylanilines with vinylethylene carbonates and vinyl epoxides has been reported, affording the 1,2,3-oxathiazolidine-2-oxides under mild reaction conditions. Further synthetic applications of 1,2,3-oxathiazolidine-2-oxides in the preparation of sulfoxides, β-amino alcohols and amines have also been demonstrated.

  据报道， N-亚磺酰基苯胺与乙烯基碳酸亚乙酯和乙烯基环氧化物在钯催化下进行[3+2]环化反应，在温和的反应条件下得到1,2,3-恶噻唑烷-2-氧化物。 1,2,3-恶噻唑烷-2-氧化物在制备亚砜、β-氨基醇和胺中的进一步合成应用也已得到证实。
• Copper-Catalyzed Rearrangement of Vinyl Oxiranes
  作者：Lindsay A. Batory、Christine E. McInnis、Jon T. Njardarson

  DOI：10.1021/ja067073o

  日期：2006.12.1

  A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.
• Highly Selective Copper-Catalyzed Ring Expansion of Vinyl Thiiranes:  Application to Synthesis of Biotin and the Heterocyclic Core of Plavix
  作者：Erik Rogers、Hiroshi Araki、Lindsay A. Batory、Christine E. McInnis、Jon T. Njardarson

  DOI：10.1021/ja069059h

  日期：2007.3.1

  We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described.