trans-2-(4-nitrophenyl)-3-vinyloxiran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-2-(4-nitrophenyl)-3-vinyloxiran
• 英文别名: (2S,3S)-2-ethenyl-3-(4-nitrophenyl)oxirane
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: MKMGBGSRUSMMMW-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-nitrophenyl)-4-tributylstannylbut-2-en-1-ol 在 碘 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以52%的产率得到trans-2-(4-nitrophenyl)-3-vinyloxiran
  参考文献：
  名称：

  Syntheses and Synthetic Applications of Stannylated Allylic Alcohols

  摘要：

  Allenyl carbinols undergo regioselective hydrostannation in the presence of MoBl(3), a catalyst originally developed for the hydrostannation of alkynes, giving rise to allyl stannanes, These allyl stannanes can easily be converted into useful synthetic building blocks such as allyl iodides or vinyl epoxides.

  DOI：

  10.1021/jo052611l

文献信息

• Novel Reaction Course of Thiiranes to Vinyloxiranes: Reaction of Benzyne with Thiiranes and Aldehydes
  作者：Kentaro Okuma、Yuxuan Qu、Noriyoshi Nagahora

  DOI：10.3987/com-21-14465

  日期：——

  Reaction of 2 molar amount of 2-(trimethylsilyl)phenyl triflate with thiiranes and aldehydes in the presence of CsF afforded vinyloxiranes in one-pot operation. Reaction of benzyne with thiiranes gave the corresponding alkenyl phenyl sulfides, which further reacted with another molar of benzyne to afford sulfonium ylide intermediates. Further treatment of aldehydes gave the corresponding vinyloxiranes

  在 CsF 存在下，2 摩尔量的 2-（三甲基甲硅烷基）苯基三氟甲磺酸酯与硫杂丙烷和醛反应，在一锅法操作中得到乙烯基环氧乙烷。苄与硫杂丙环反应得到相应的烯基苯基硫化物，其进一步与另一摩尔的苄反应得到锍叶立德中间体。醛的进一步处理得到相应的乙烯基环氧乙烷。
• A facile tetrahydrothiophene-catalyzed ylide route to vinyloxiranesElectronic supplementary information (ESI) available: preparation of vinyloxiranes and chiral catalysts. See http://www.rsc.org/suppdata/cc/b3/b304443b/
  作者：Kai Li、Xian-Ming Deng、Yong Tang

  DOI：10.1039/b304443b

  日期：——

  Access to vinyloxiranes using aldehydes and allylic bromides in the presence of 1–5 mol% tetrahydrothiophene is reported. Both aliphatic and aromatic aldehydes work well in this reaction and the catalyst loading could be reduced as low as 0.5 mol%.

  据报道，在 1-5 摩尔% 的四氢噻吩存在下，使用醛和烯丙基溴可以获得乙烯基环氧乙烷。脂肪醛和芳香醛在该反应中都能很好地发挥作用，催化剂的负载量可降低到 0.5 摩尔%。
• A first example of catalytic ylide epoxidation reaction: facile synthesis of vinyl epoxides from aldehydes catalyzed by diisobutyl telluride
  作者：Zhang-Lin Zhou、Shi Li-Lan、Yao-Zeng Huang

  DOI：10.1016/s0040-4039(00)97324-6

  日期：1990.1

  presence of cesium carbonate, a variety of aldehydes can be epoxidized directly with allyl bromide at 50°C under solid-liquid phase transfer condition by use of a catalytic amount of diisobutyl telluride to afford vinyl epoxides in good yields with predominant cis stereoselectivity.

  在碳酸铯的存在下，可以通过使用催化量的二异丁基碲化物，在固液相转移条件下于50°C用烯丙基溴直接环氧化各种醛，从而以良好的收率和主要的顺式立体选择性获得乙烯基环氧化物。
• Syntheses and Synthetic Applications of Stannylated Allylic Alcohols
  作者：Uli Kazmaier、Simon Lucas、Manuela Klein

  DOI：10.1021/jo052611l

  日期：2006.3.1

  Allenyl carbinols undergo regioselective hydrostannation in the presence of MoBl(3), a catalyst originally developed for the hydrostannation of alkynes, giving rise to allyl stannanes, These allyl stannanes can easily be converted into useful synthetic building blocks such as allyl iodides or vinyl epoxides.