methyl (Z)-2-methyl-4-oxo-3-phenylpent-2-enoate | 1346642-60-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (Z)-2-methyl-4-oxo-3-phenylpent-2-enoate
• CAS: 1346642-60-1
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: RSUWUNNAQVIAOY-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-methyl-4-oxo-3-phenylpent-2-enoate 、 3-溴丙烯 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以73%的产率得到3,5-Dimethyl-4-phenyl-5-prop-2-enylfuran-2-one
  参考文献：
  名称：

  Facile synthesis of γ-alkenylbutenolides from Baylis–Hillman adducts: consecutive in-mediated Barbier allylation, PCC oxidation, isomerization, and Zn-mediated Barbier allylation

  摘要：

  Alkenylbutenolides were synthesized regioselectively in good to moderate yields from Baylis-Hillman adducts via a consecutive indium-mediated Barbier type reaction between Baylis-Hillman bromide and aldehyde, PCC oxidation of the homoallylic alcohol, double bond isomerization, and zinc-mediated Barbier type alkenylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.125
• 作为产物：
  描述：

  2-(acetoxy-phenyl-methyl)acrylic acid methyl ester 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以67%的产率得到methyl (Z)-2-methyl-4-oxo-3-phenylpent-2-enoate
  参考文献：
  名称：

  Facile synthesis of γ-alkenylbutenolides from Baylis–Hillman adducts: consecutive in-mediated Barbier allylation, PCC oxidation, isomerization, and Zn-mediated Barbier allylation

  摘要：

  Alkenylbutenolides were synthesized regioselectively in good to moderate yields from Baylis-Hillman adducts via a consecutive indium-mediated Barbier type reaction between Baylis-Hillman bromide and aldehyde, PCC oxidation of the homoallylic alcohol, double bond isomerization, and zinc-mediated Barbier type alkenylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.125

文献信息

• Facile synthesis of γ-alkenylbutenolides from Baylis–Hillman adducts: consecutive in-mediated Barbier allylation, PCC oxidation, isomerization, and Zn-mediated Barbier allylation
  作者：Jin Woo Lim、Ko Hoon Kim、Bo Ram Park、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2011.09.125

  日期：2011.12

  Alkenylbutenolides were synthesized regioselectively in good to moderate yields from Baylis-Hillman adducts via a consecutive indium-mediated Barbier type reaction between Baylis-Hillman bromide and aldehyde, PCC oxidation of the homoallylic alcohol, double bond isomerization, and zinc-mediated Barbier type alkenylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.