(E)-ethyl 5-(4-Methoxyphenyl)-4-penten-2-ynoate | 1620092-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-ethyl 5-(4-Methoxyphenyl)-4-penten-2-ynoate
• 英文别名: ethyl (E)-5-(4-methoxyphenyl)pent-4-en-2-ynoate
• CAS: 1620092-38-7
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: UTKAVIOIOXDLKR-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (E)-ethyl 5-(4-Methoxyphenyl)-4-penten-2-ynoate 、 9-(2-phenylethyl)-9-borabicyclo[3.3.1]nonane 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (2E,4E)-ethyl 3-{9-borabicyclo[3.3.1]nonan-9-yl}-5-(4-methoxyphenyl)-2-phenethyl-2,4-pentadienoate
  参考文献：
  名称：

  Phosphine-Catalyzed Anti-Carboboration of Alkynoates with Alkyl-, Alkenyl-, and Arylboranes

  摘要：

  We found that trialkylphosphine organo-catalysts promoted unprecedented anti-carboboration of alkynoates with alkyl-, alkenyl-, or arylboranes to form beta-boryl acrylates. The regioselectivity of the carboboration across the polar C-C triple bond exhibited inverse electronic demand, with the less electronegative B atom being delivered to the positively charged beta carbon atom. The regioselectivity and the anti stereoselectivity were both complete and robust. In addition, the substrate scope was broad with excellent functional group compatibility.

  DOI：

  10.1021/ja506310v

文献信息

• Phosphine-Catalyzed <i>Anti</i>-Hydroboration of Internal Alkynes
  作者：Kazunori Nagao、Ayaka Yamazaki、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/acs.orglett.8b00390

  日期：2018.4.6

  Trialkylphosphine organocatalysts have enabled regioselective anti-hydroboration of internal, alkynes with pinacolborane reagents to provide (E)-disubstituted alkenylboronate compounds. The alkenyl-boronate can be used for derivatizations, such as protodeborylation, Suzuld-Miyaura coupling, conjugate reduction, and Diels-Alder reactions.