(+/-)-2-furyl 2-phenoxypropanoate

• 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: (+/-)-2-furyl 2-phenoxypropanoate
• 英文别名: Furan-2-yl 2-phenoxypropanoate；furan-2-yl 2-phenoxypropanoate
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: XCMDZRJIEBNKEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二溴-3-戊酮 、 (+/-)-2-furyl 2-phenoxypropanoate 在 铜 、 sodium iodide 作用下， 以 乙腈 为溶剂， 生成 2,4-dimethyl-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-1-yl (+/-)-2-phenoxypropanoate 、 2,4-dimethyl-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-1-yl (+/-)-2-phenoxypropanoate
  参考文献：
  名称：

  Asymmetry induction on the [4C(4π)+3C(2π)] cycloaddition reaction of C2-functionalized furans: influence of the chiral auxiliary nature

  摘要：

  The study of the pi-facial diastereoselectivity in the [4+3] cycloaddition reaction of thirteen different chiral 2-substituted furans with oxyallyl cations, under sonochemical and/or thermal conditions, is presented. In almost all studied furans, a cis diastereoselectivity and a high endo diastereoselectivity is observed. Decreasing the distance between the closest stereocenter of the chiral auxiliary and the reactive C2-carbon of the furan ring, increases the pi-facial diastereoselectivity, especially by using chiral furyl-sulfoxides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00452-0
• 作为产物：
  描述：

  2(5H)-呋喃酮 、 2-苯氧基丙酰氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 以13%的产率得到(+/-)-2-furyl 2-phenoxypropanoate
  参考文献：
  名称：

  Asymmetry induction on the [4C(4π)+3C(2π)] cycloaddition reaction of C2-functionalized furans: influence of the chiral auxiliary nature

  摘要：

  The study of the pi-facial diastereoselectivity in the [4+3] cycloaddition reaction of thirteen different chiral 2-substituted furans with oxyallyl cations, under sonochemical and/or thermal conditions, is presented. In almost all studied furans, a cis diastereoselectivity and a high endo diastereoselectivity is observed. Decreasing the distance between the closest stereocenter of the chiral auxiliary and the reactive C2-carbon of the furan ring, increases the pi-facial diastereoselectivity, especially by using chiral furyl-sulfoxides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00452-0