[(Z)-1-cyclohexylidenebut-2-en-2-yl] 2,2-dimethylpropanoate | 1016669-40-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(Z)-1-cyclohexylidenebut-2-en-2-yl] 2,2-dimethylpropanoate
• CAS: 1016669-40-1
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: HKAGLPQWMNUUDR-ACAGNQJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-Cyclohexylbut-3-yn-2-yl 2,2-dimethylpropanoate 在 iPrAuNTf₂ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 [(Z)-1-cyclohexylidenebut-2-en-2-yl] 2,2-dimethylpropanoate 、
  参考文献：
  名称：

  Au-Catalyzed Synthesis of (1Z,3E)-2-Pivaloxy-1,3-Dienes from Propargylic Pivalates

  摘要：

  Propargylic pivalates with electronically unbiased internal alkynes are selectively transformed into (1Z,3E)-2-pivaloxy-1,3-dienes containing various functionalities. The unusual selectivity of 1,2-acyloxy migration over the structurally preferred 3,3-rearrangement is realized. This reaction is highly stereoselective and offers rapid access to dienes for one-pot intra-/intermolecular Diels-Alder reactions either under thermal conditions or with Lewis acid catalysis.

  DOI：

  10.1021/ja800001h

文献信息

• Au-Catalyzed Synthesis of (1<i>Z</i>,3<i>E</i>)-2-Pivaloxy-1,3-Dienes from Propargylic Pivalates
  作者：Guotao Li、Guozhu Zhang、Liming Zhang

  DOI：10.1021/ja800001h

  日期：2008.3.1

  Propargylic pivalates with electronically unbiased internal alkynes are selectively transformed into (1Z,3E)-2-pivaloxy-1,3-dienes containing various functionalities. The unusual selectivity of 1,2-acyloxy migration over the structurally preferred 3,3-rearrangement is realized. This reaction is highly stereoselective and offers rapid access to dienes for one-pot intra-/intermolecular Diels-Alder reactions either under thermal conditions or with Lewis acid catalysis.