5-(2,5-dimethoxyphenyl)pent-4-ynal | 950205-92-2

• 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: 5-(2,5-dimethoxyphenyl)pent-4-ynal
• CAS: 950205-92-2
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: LNERRNMHTGTTNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2,5-dimethoxyphenyl)pent-4-ynal 在 palladium on activated charcoal ammonium cerium(IV) nitrate 、 三氟化硼乙醚 、 甲基锂 、 氢气 、 叔丁基锂 、 对甲苯磺酸 、 苯乙醚 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 、 水 、 乙腈 、 正戊烷 、 苯 为溶剂， 反应 15.49h， 生成 (+/-)-frondosin B
  参考文献：
  名称：

  Total Synthesis of (±)-Frondosin B

  摘要：

  An expeditious reaction sequence featuring a microwave-assisted tandem 5-exo cyclization-Claisen rearrangement process was used to assemble the A/B ring system of frondosin B. Completion of the target natural product was achieved in 38.2% yield over an eight-step linear sequence.

  DOI：

  10.1021/ol701633z
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基苯 在 四(三苯基膦)钯 copper(l) iodide 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(2,5-dimethoxyphenyl)pent-4-ynal
  参考文献：
  名称：

  Synthesis of Seven-Membered Carbocyclic Rings via a Microwave-Assisted Tandem Oxyanionic 5-exo dig Cyclization−Claisen Rearrangement Process

  摘要：

  Appropriately substituted 1-alkenyl-4-pentyn-l-ol systems, readily prepared from simple starting materials, serve as useful precursors to a number of substituted cyclohept-4-enone derivatives via a microwave-assisted tandem oxyanionic 5-exo cyclization/Claisen rearrangement sequence. The reactions involving terminally substituted 4-pentyn-1-ols were found to be highly stereoselective, with the a and beta groups in the final product showing a strong preference for the trans orientation.

  DOI：

  10.1021/jo0710432

文献信息

• Synthesis of Seven-Membered Carbocyclic Rings via a Microwave-Assisted Tandem Oxyanionic 5-<i>exo</i> <i>dig</i> Cyclization−Claisen Rearrangement Process
  作者：Xin Li、Robert E. Kyne、Timo V. Ovaska

  DOI：10.1021/jo0710432

  日期：2007.8.1

  Appropriately substituted 1-alkenyl-4-pentyn-l-ol systems, readily prepared from simple starting materials, serve as useful precursors to a number of substituted cyclohept-4-enone derivatives via a microwave-assisted tandem oxyanionic 5-exo cyclization/Claisen rearrangement sequence. The reactions involving terminally substituted 4-pentyn-1-ols were found to be highly stereoselective, with the a and beta groups in the final product showing a strong preference for the trans orientation.
• Total Synthesis of (±)-Frondosin B
  作者：Xin Li、Timo V. Ovaska

  DOI：10.1021/ol701633z

  日期：2007.9.1

  An expeditious reaction sequence featuring a microwave-assisted tandem 5-exo cyclization-Claisen rearrangement process was used to assemble the A/B ring system of frondosin B. Completion of the target natural product was achieved in 38.2% yield over an eight-step linear sequence.