4-hydroxy-2-(1-hydroxy-1-methylethenyl)benzofuran-5-carboxaldehyde | 162794-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-hydroxy-2-(1-hydroxy-1-methylethenyl)benzofuran-5-carboxaldehyde
• 英文别名: 2-isopropenyl-4-hydroxybenzofuran-5-carboxaldehyde；4-hydroxy-2-isopropenyl-benzofuran-5-carbaldehyde；4-Hydroxy-2-isopropenyl-benzofuran-5-carbaldehyd；5-Benzofurancarboxaldehyde, 4-hydroxy-2-(1-methylethenyl)-；4-hydroxy-2-prop-1-en-2-yl-1-benzofuran-5-carbaldehyde
• CAS: 162794-50-5
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: OOKKQWASZWHYQI-UHFFFAOYSA-N

物化性质

• 沸点：
  244.4±15.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 4-hydroxy-2-(1-hydroxy-1-methylethenyl)benzofuran-5-carboxaldehyde 在 甲醇 、 乙醚 作用下， 生成 2-isopropenyl-4-methoxy-benzofuran-5-carbaldehyde
  参考文献：
  名称：

  Spaeth; Schmid, Chemische Berichte, 1940, vol. 73, p. 1309,1312, 1316

  摘要：

  DOI：
• 作为产物：
  描述：

  5-hydroxymethylene-2-isopropenyl-4,5,6,7-tetrahydrobenzofuran-4-one enol form 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 以72%的产率得到4-hydroxy-2-(1-hydroxy-1-methylethenyl)benzofuran-5-carboxaldehyde
  参考文献：
  名称：

  A concise new synthesis of angular furanocoumarins: Angelicin, oroselone & oroselol

  摘要：

  An efficient synthesis of angular furanocoumarins has been carried out starting from dihydrobenzofuran derivatives.

  DOI：

  10.1016/0040-4020(95)00070-o

文献信息

• Synthesis of 2,3-Dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from Epoxy Aldehydes. One-Step Syntheses of Brosimacutin G, Vaginidiol, Vaginol, Smyrindiol, Xanthoarnol, and Avicenol A. Biomimetic Syntheses of Angelicin and Psoralen
  作者：Yefen Zou、Mercedes Lobera、Barry B. Snider

  DOI：10.1021/jo047974k

  日期：2005.3.1

  [GRAPHICS]We have developed two practical one-step syntheses of 2,3-dihydro-3-hydroxy-2-hydroxyalkylbenzofurans from readily available optically pure alpha,beta-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH/CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy iodocoumarins 35d and 40 and acetoxy bromonaphthalene 41 add to epoxy aldehyde (S)-26 to complete the first syntheses of vaginidiol (7c), vaginol (7t), smyrindiol (8c), xanthoarnol (8t), and avicenol A (9t). Acid-catalyzed fragmentation of vaginidiol or vaginol provides angelicin, while that of smyrindiol or xanthoarnol affords psoralen. In both cases, the trans isomers fragment only twice as fast as the cis isomers, possibly through the intermediacy of a common benzylic cation. This may have implications for the biosynthesis of angelicin and psoralen.
• Lemmich et al., Acta Chemica Scandinavica (1947), 1970, vol. 24, p. 2893,2896, 2897 Anm.
  作者：Lemmich et al.

  DOI：——

  日期：——
• The absolute configurations of athamantin and edultin
  作者：Masao Nakazaki、Yoshiki Hirose、Kiyoshi Ikematsu

  DOI：10.1016/s0040-4039(00)72934-0

  日期：1966.1