3-acetoxy-1-ethoxy-3-phenyl-1-propyne

• 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: 3-acetoxy-1-ethoxy-3-phenyl-1-propyne
• 英文别名: (3-Ethoxy-1-phenylprop-2-ynyl) acetate；(3-ethoxy-1-phenylprop-2-ynyl) acetate
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: UZVOAVONDQGWGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：

  3-acetoxy-1-ethoxy-3-phenyl-1-propyne 在 水 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.67h， 以77%的产率得到肉桂酸乙酯
  参考文献：
  名称：

  Virtually Complete E-Selective α,β-Unsaturated Ester Synthesis by Hg(OTf)₂-Catalyzed Hydration of sec-Ethoxyalkynyl Acetate

  摘要：

  The reaction of alkyl-substituted sec-ethoxyalkynyl acetates with water catalyzed by Hg(OTf)(2) afforded alpha,beta-unsaturated esters in excellent yield with high catalytic turnover up to 1000 times under very mild reaction conditions with virtually complete E-selectivity, superior even to that of the HWE reaction.

  DOI：

  10.1021/ol702548r

文献信息

• Rearrangement of Propargylic Esters:  Metal-Based Stereospecific Synthesis of (<i>E</i>)- and (Z)-Knoevenagel Derivatives
  作者：José Barluenga、Lorena Riesgo、Rubén Vicente、Luis A. López、Miguel Tomás

  DOI：10.1021/ja072864r

  日期：2007.6.1

  catalysts perform the isomerization with complementary Z/E selectivity. Moreover, alkynyl-conjugated Knoevenagel products are produced from (bisalkynyl)methyl acetates. In such a case, the reaction is chemoselective as the 1,3-acetyl migration takes place through the alkoxyalkyne group in preference over the phenylalkyne group. The resulting (E)-alkynylenone unit suffers metal-catalyzed cyclization

  烷氧基取代的炔丙酯在 Pt(II) 和 Cu(I) 催化剂存在下进行区域选择性 1,3-酰氧基迁移，从而可以制备 α-亚基-β-酮和丙二酸酯。该反应也被证明是立体发散的，因为 Pt(II) 和 Cu(I) 催化剂以互补的 Z/E 选择性进行异构化。此外，炔基共轭的 Knoevenagel 产品是由（双炔基）甲基乙酸酯生产的。在这种情况下，反应是化学选择性的，因为 1,3-乙酰基迁移优先通过烷氧基炔基而不是苯炔基。所得的 (E)-炔烃单元在金属催化下环化成呋喃环，生成铜 (I) 卡宾物质。
• Virtually Complete <i>E</i>-Selective α,β-Unsaturated Ester Synthesis by Hg(OTf)₂-Catalyzed Hydration of <i>sec</i>-Ethoxyalkynyl Acetate
  作者：Mugio Nishizawa、Hiroko Hirakawa、Yuki Nakagawa、Hirofumi Yamamoto、Kosuke Namba、Hiroshi Imagawa

  DOI：10.1021/ol702548r

  日期：2007.12.1

  The reaction of alkyl-substituted sec-ethoxyalkynyl acetates with water catalyzed by Hg(OTf)(2) afforded alpha,beta-unsaturated esters in excellent yield with high catalytic turnover up to 1000 times under very mild reaction conditions with virtually complete E-selectivity, superior even to that of the HWE reaction.