(E,Z)-3-(4-hydroxy-3-methoxybenzylidene)-tetrahydrofuran-2,4-dione | 1123756-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E,Z)-3-(4-hydroxy-3-methoxybenzylidene)-tetrahydrofuran-2,4-dione
• CAS: 1123756-57-9
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: JQMREUKHGOJYPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E,Z)-3-(4-hydroxy-3-methoxybenzylidene)-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， 以90%的产率得到3-(4-hydroxy-3-methoxybenzyl)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：

  4-羟乙酰乙酸内酯 、 香草醛 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以89%的产率得到(E,Z)-3-(4-hydroxy-3-methoxybenzylidene)-tetrahydrofuran-2,4-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1134/s1070428008050047

文献信息

• Tetronic acid in reaction with aromatic aldehydes and 2-naphthylamine. Investigation of fluorescent and nonlinear-optical characteristics of compounds obtained
  作者：N. G. Kozlov、S. L. Bondarev、A. P. Kadutskii、L. I. Basalaeva、F. S. Pashkovskii

  DOI：10.1134/s1070428008070142

  日期：2008.7

  By Knoevenagel condensation and by three-component condensation 3-arylmethylenetetrahydrofuran-2,4-diones and previously unknown 8,11-dihydro-11-arylbenzo[f]furo[3,4-b]quinolin-10(7H)-ones were respectively synthesized. The luminescent spectra and nonlinear-optical characteristics of compounds obtained were investigated.
• 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.
• Chemoselective reduction of 3-arylmethylidenetetrahydrofuran-2,4-diones with triethylsilane and sodium cyanotrihydridoborate in acid media
  作者：F. S. Pashkovskii、E. M. Shchukina、F. A. Lakhvich

  DOI：10.1134/s1070428009060098

  日期：2009.6

  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.