2-(4,4-bis(benzyloxymethyl)oct-6-yn-2-yl)-1,3-dioxolane | 1256270-39-9

• 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: 2-(4,4-bis(benzyloxymethyl)oct-6-yn-2-yl)-1,3-dioxolane
• CAS: 1256270-39-9
• 化学式: C₂₇H₃₄O₄
• 分子量: 422.565
• InChiKey: IENFYIJKLDSSKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4,4-bis(benzyloxymethyl)oct-6-yn-2-yl)-1,3-dioxolane 在 APTS 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 14.0h， 以56%的产率得到4,4-bis(benzyloxymethyl)-2-methyloct-6-ynal
  参考文献：
  名称：

  InCl₃/CyNH₂ Cocatalyzed Carbocyclization Reaction: An Entry to α-Disubstituted exo-Methylene Cyclopentanes

  摘要：

  An efficient and cheap synthetic approach to functionalized exo-methylene cyclopentanes has been developed from alpha-disubstituted formyl-alkynes by merging amine catalysis with the indium activation of alkynes. We uncovered the crucial role of the amine cocatalyst and the development of a new cooperative catalytic system allowed the cyclization of a broad range of substrates. A mechanistic study was realized in order to rationalize the determining influence of the amine cocatalyst.

  DOI：

  10.1021/jo1018552
• 作为产物：
  描述：

  2-(4,4-bis(benzyloxymethyl)hept-6-yn-2-yl)-1,3-dioxolane 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以68%的产率得到2-(4,4-bis(benzyloxymethyl)oct-6-yn-2-yl)-1,3-dioxolane
  参考文献：
  名称：

  InCl₃/CyNH₂ Cocatalyzed Carbocyclization Reaction: An Entry to α-Disubstituted exo-Methylene Cyclopentanes

  摘要：

  An efficient and cheap synthetic approach to functionalized exo-methylene cyclopentanes has been developed from alpha-disubstituted formyl-alkynes by merging amine catalysis with the indium activation of alkynes. We uncovered the crucial role of the amine cocatalyst and the development of a new cooperative catalytic system allowed the cyclization of a broad range of substrates. A mechanistic study was realized in order to rationalize the determining influence of the amine cocatalyst.

  DOI：

  10.1021/jo1018552