3-(4-fluorophenyl)-2-methylene-5-phenylpent-4-ynenitrile | 1072836-68-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-(4-fluorophenyl)-2-methylene-5-phenylpent-4-ynenitrile
• CAS: 1072836-68-0
• 化学式: C₁₈H₁₂FN
• 分子量: 261.298
• InChiKey: PUMDEONZVKVELL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (碘乙炔基)苯 、 Acetic acid 2-cyano-1-(4-fluoro-phenyl)-allyl ester 在 indium 、 indium(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 3-(4-fluorophenyl)-2-methylene-5-phenylpent-4-ynenitrile 、 (2Z)-2-[(4-fluorophenyl)methylidene]-5-phenylpent-4-ynenitrile
  参考文献：
  名称：

  Indium-mediated alkynylation of Baylis–Hillman acetates: a novel route to 1,4-enynes

  摘要：

  Baylis-Hillman acetates undergo smooth alkynylation with aryl-susbstituted iodoalkynes in the presence of indium metal in refluxing dichloromethane to furnish 1,4-enynes in high yields with (E)-stereoselectivity. In the absence of Lewis acid, the reaction follows both S(N)2 and S(N)2' pathways affording 1:1 mixtures of 1,4-enynes. Upon addition of 10 mol % of InBr(3), the reaction proceeds preferably in the S(N)2' manner. In the case of adducts derived from acrylonitrile, the corresponding products are obtained in fairly good yields and with (Z)-stereoselectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.019