6-methylhept-6-en-4-yn-3-yl acetate | 1385017-85-5

• 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: 6-methylhept-6-en-4-yn-3-yl acetate
• 英文别名: 6-Methylhept-6-en-4-yn-3-yl acetate
• CAS: 1385017-85-5
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: TZBREGUFZCWLLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methylhept-6-en-4-yn-3-yl acetate 在 silver hexafluoroantimonate 、 三苯基膦氯金 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以74%的产率得到4-ethyl-2-methylcyclopenta-1,4-dienyl acetate
  参考文献：
  名称：

  “Silver Effect” in Gold(I) Catalysis: An Overlooked Important Factor

  摘要：

  Clear experimental evidence from X-ray photoelectron spectroscopy and P-31 NMR spectroscopy has been obtained for the first time to confirm that the combination of Ag+ cation with [L-Au](+) results in the formation of different complexes in solution. Re-evaluation of literature-reported gold-catalyzed reactions revealed a significant difference in the reactivities with and without silver. In extreme cases (more than "rare"), the conventional [L-Au](+) catalysts could not promote the reaction without the presence of silver. This investigation has therefore revealed a long-overlooked "silver effect" in gold catalysis and should lead to revision of the actual mechanism.

  DOI：

  10.1021/ja303862z
• 作为产物：
  描述：

  2-甲基-1-丁烯-3-炔 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 6-methylhept-6-en-4-yn-3-yl acetate
  参考文献：
  名称：

  Diastereoselective [4 + 1] Cycloaddition of Alkenyl Propargyl Acetates with CO Catalyzed by [RhCl(CO)₂]₂

  摘要：

  A class of alkenyl propargyl acetates, RCH(OAc)C CC(CH3)=CH2 (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.

  DOI：

  10.1021/jo3009403