3-(3-phenylprop-2-en-1-yl)tetrahydrofuran-2,4-dione | 1123757-03-8

• 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-(3-phenylprop-2-en-1-yl)tetrahydrofuran-2,4-dione
• 英文别名: 3-cinnamyltetrahydrofuran-2,4-dione
• CAS: 1123757-03-8
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: SGFXQZXOSAMLFA-QPJJXVBHSA-N

物化性质

• 熔点：
  153-156 °C
• 沸点：
  426.5±38.0 °C(predicted)
• 密度：
  1.206±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(3-phenylprop-2-en-1-yl)tetrahydrofuran-2,4-dione 在 三乙基硅烷 、 lithium perchlorate 作用下， 以 三氟乙酸 为溶剂， 反应 48.0h， 以79%的产率得到3-(3-phenylpropyl)tetrahydrofuran-2,4-dione
  参考文献：
  名称：

  Chemoselective reduction of 3-arylmethylidenetetrahydrofuran-2,4-diones with triethylsilane and sodium cyanotrihydridoborate in acid media

  摘要：

  3-Arylmethylidenetetrahydrofuran-2,4-diones were smoothly reduced to the corresponding 3-benzyl derivatives in 50-98% yield with triethylsilane in trifluoroacetic acid or with sodium cyanotrihydridoborate in the system tetrahydrofuran-2 N hydrochloric acid. The reduction of 3-(3-arylprop-2-en-1-ylidene)-tetrahydrofuran-2,4-diones with sodium cyanotrihydridoborate gave 3-cinnamyltetrahydrofuran-2,4-diones as the only products.

  DOI：

  10.1134/s1070428009060098
• 作为产物：
  描述：

  (E,Z)-3-[(E)-3-phenylallylidene]tetrahydrofuran-2,4-dione 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 盐酸 、 水 为溶剂， 反应 12.0h， 生成 3-(3-phenylprop-2-en-1-yl)tetrahydrofuran-2,4-dione
  参考文献：
  名称：

  Chemoselective reduction of 3-arylmethylidenetetrahydrofuran-2,4-diones with triethylsilane and sodium cyanotrihydridoborate in acid media

  摘要：

  3-Arylmethylidenetetrahydrofuran-2,4-diones were smoothly reduced to the corresponding 3-benzyl derivatives in 50-98% yield with triethylsilane in trifluoroacetic acid or with sodium cyanotrihydridoborate in the system tetrahydrofuran-2 N hydrochloric acid. The reduction of 3-(3-arylprop-2-en-1-ylidene)-tetrahydrofuran-2,4-diones with sodium cyanotrihydridoborate gave 3-cinnamyltetrahydrofuran-2,4-diones as the only products.

  DOI：

  10.1134/s1070428009060098

文献信息

• Heterocyclic analogs of prostaglandines: IV. Synthesis of 3,7-interphenylene 3,10(11)-dioxa-13-azaprostanoids and 9-oxa-7-azaprostanoids based on tetronic acid and aromatic aldehydes
  作者：F. S. Pashkovskii、E. M. Shchukina、M. G. Gribovskii、F. A. Lakhvich

  DOI：10.1134/s1070428008050047

  日期：2008.5

  An approach was developed to the synthesis of stable in metabolism 3,7-interphenylene 3,10-dioxa-13-aza-and 3,11-dioxa-13-azaprostanoids, and also 9-oxa-7-azaprostanoids with interphenylene and terminal phenyl fragments in the omega-chain based on 3-(alkoxybenzylidene)-and 3-(3-phenylallylidene)tetrahydrofuran-2,4-diones obtained by Knoevenagel condensation of tetronic acid with alkoxy-substituted aromatic aldehydes and cinnamic aldehyde.