trans-2-(4-methylphenyl)-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-methylphenyl)-3-vinyloxiran
• 英文别名: (2S,3S)-2-ethenyl-3-(4-methylphenyl)oxirane
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: MURJXIJWIUNIOW-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(p-tolyl)buta-2,3-dien-1-ol 在 Mo(CO)3(CN-t-Bu)3 、 碘 、 对苯二酚 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.0h， 生成 trans-2-(4-methylphenyl)-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。
• Reaction of 3-chloroallyltrimethylsilane with acid chloride and exploitation of a new regioselective synthesis of αβ-unsaturated epoxide
  作者：Masahito Ochiai、Eiichi Fujita

  DOI：10.1016/s0040-4039(00)77860-9

  日期：1980.1

  reaction of 3-chloroallyltrimethylsilane (1) with acid chloride. The ketone was converted into αβ-unsaturated epoxide (3) regioselectively in good yield via reduction with NaBH4 or LiAlH4 followed by treatment with NaOH. Treatment with methyl lithium instead of reduction gave homologous epoxide (5).

  由3-氯烯丙基三甲基硅烷（1）与酰氯反应合成α-氯-βγ-不饱和酮（2）。通过用NaBH 4或LiAlH 4还原，然后用NaOH处理，将酮以良好的产率选择性地转化为αβ-不饱和环氧化物（3）。用甲基锂而不是还原的处理得到同源的环氧化物（5）。
• 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.