3,4-dihydro-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one | 80458-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,4-dihydro-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one
• 英文别名: 3-(4-hydroxyphenyl)-3,4-dihydro-1H-isochromen-1-one；(dl)-3-(4'-hydroxyphenyl)-3,4-dihydroisocoumarin；3,4-dihydro-3-(p-hydroxyphenyl)isocoumarin；3-(4-hydroxyphenyl)isochroman-1-one；3-(4-hydroxyphenyl)-3,4-dihydroisochromen-1-one
• CAS: 80458-97-5；148324-43-0
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: ULRDHQZUWUVIGG-UHFFFAOYSA-N

物化性质

• 熔点：
  162 °C(Solv: methanol (67-56-1))
• 沸点：
  463.5±45.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one 在 水 、 potassium carbonate 、 sodium hydroxide 、 N,N'-二异丙基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Reduction of 3-(carboxyaryl)isocoumarins with sodium borohydride

  摘要：

  Reduction of 3-(carboxyaryl)isocoumarins with sodium borohydride proceeds with formation of corresponding 3-carboxyaryl-3,4-dihydroisocoumarins or isomeric dihydrophthalides, 3-(2-carboxybenzyl)-2-benzofuran-1(3H)-ones. Derivatives at the carboxyl group of 3-carboxyaryl-3,4-dihydroisocoumarins and 3-(2-carboxybenzyl)-2-benzofuran-1(3H)-ones have been obtained.

  DOI：

  10.1007/s10593-012-0896-3
• 作为产物：
  描述：

  邻甲基苯甲酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 0.5h， 生成 3,4-dihydro-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one
  参考文献：
  名称：

  Stereoselective synthesis of hydroxy stilbenoids and styrenes by atom-efficient olefination with thiophthalides

  摘要：

  在碱性条件下，通过硫代邻苯二甲酸酯对醛进行烯化反应，可以高E-立体选择性地合成芪类化合物和苯乙烯基羧酸。该烯化反应具有高度的原子效率，因为在反应过程中仅损失了元素硫。这种烯化反应与逆科尔比-施密特反应相结合，能够简便地合成E-羟基芪类化合物，并最小程度地使用保护基团。这项研究还揭示了两个重要发现：i) 形成4-甲硫基异香豆素和ii) 形成2-芳基茚满酮。

  DOI：

  10.1039/c2ob06991a

文献信息

• Syntheses of antifungal isocoumarins. II. Synthesis and antifungal activity of 3-substituted isocoumarins.
  作者：KOOHEI NOZAWA、MIKIKO YAMADA、YOSHIKO TSUDA、KENICHI KAWAI、SHOICHI NAKAJIMA

  DOI：10.1248/cpb.29.2491

  日期：——

  Various 3-arylisocoumarins (5, 6, 8, 10, 11, and 12) were simply prepared in high yields by heating homophthalic acids (1-4) with aromatic acyl chlorides. 8-Hydroxy-3-phenylisocoumarin (17) and 8-acetoxy-3-phenylisocoumarin (18), and 8-hydroxy-3-(p-methoxyphenyl) isocoumarin (19) were obtained by alkaline hydrolysis of 10 and 11, respectively, followed by treatment with acetic anhydride. 3, 4-Dihydro-8-hydroxy-3-phenyl-isocoumarin (24) was prepared from 10 by alkaline hydrolysis followed by reduction with sodium borohydride then heating with acetic anhydride. 3-(p-Hydroxyphenyl)-isocoumarin (7), 8-hydroxy-3-(p-hydroxyphenyl) isocoumarin (9), 5-chloro-8-hydroxy-6-methoxy-3-phenylisocoumarin (13), and 3, 4-dihydro-3-(p-hydroxyphenyl) isocoumarin (23) were prepared by demethylation of 6, 8, 12 and 22, respectively. All the prepared isocoumarins and some other isocoumarin derivatives (25-30) were examined in vitro for antifungal activity. The structure-activity relationships are discussed.

  通过加热均苯二甲酸（1-4）和芳香酰基氯，可以简单地高产率制备出各种 3-芳基异香豆素（5、6、8、10、11 和 12）。8- 羟基-3-苯基异香豆素（17）和 8-乙酰氧基-3-苯基异香豆素（18）以及 8-羟基-3-（对甲氧基苯基）异香豆素（19）分别是通过碱水解 10 和 11，然后用乙酸酐处理而得到的。3，4-二氢-8-羟基-3-苯基异香豆素（24）是由 10 通过碱性水解，然后用硼氢化钠还原，再用乙酸酐加热制备的。3-（对羟基苯基）-异香豆素（7）、8-羟基-3-（对羟基苯基）异香豆素（9）、5-氯-8-羟基-6-甲氧基-3-苯基异香豆素（13）和 3，4-二氢-3-（对羟基苯基）异香豆素（23）分别由 6、8、12 和 22 脱甲基制备而成。对所有制备的异香豆素及其他一些异香豆素衍生物（25-30）进行了体外抗真菌活性检测。本文对其结构-活性关系进行了讨论。
• Expeditious synthesis of 3,4-dihydroisocoumarins and phthalides using the Heck–Matsuda reaction
  作者：Eduardo T. da Penha、José Augusto Forni、André F.P. Biajoli、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2011.09.014

  日期：2011.11

  Several 3,4-dihydroisocoumarins and phthalides were synthesized by an effective Heck-Matsuda reaction involving an ortho carboxybenzenediazonium salt with a series of styrenes bearing electron donating and electron withdrawing groups, methylvinyl ketone, and methyl acrylate. The reaction was carried out in an open-flask with 1% mol of palladium acetate in aqueous ethanol at similar to 80 degrees C, giving the correspondent 3-aryl-3,4-dihydroisocoumarins and phthalides with good overall yields. The electronic nature of the group attached to the olefin is a key feature for the regioselectivity of the cyclization step. (C) 2011 Elsevier Ltd. All rights reserved.
• Bellinger, Geoffrey C. A.; Campbell, William E.; Giles, Robin G. F., Journal of the Chemical Society. Perkin transactions I, 1982, # 12, p. 2819 - 2826
  作者：Bellinger, Geoffrey C. A.、Campbell, William E.、Giles, Robin G. F.、Tobias, Julius D.

  DOI：——

  日期：——
• Ahmad, Hafiz B.; Rama, Nasim H.; Hussain, Mazhar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 3, p. 611 - 615
  作者：Ahmad, Hafiz B.、Rama, Nasim H.、Hussain, Mazhar、Hussain, Muhammad T.、Qasim, Malik M.、Hameed, Shahid、Malana, Muhammad A.、Malik, Abdul

  DOI：——

  日期：——
• NOZAWA, KOOHEI;YAMADA, MIKIKO;TSUDA, YOSHIKO;KAWAI, KEN-ICHI;NAKAJIMA, SH+, CHEM. AND PHARM. BULL., 1981, 29, N 9, 2491-2495
  作者：NOZAWA, KOOHEI、YAMADA, MIKIKO、TSUDA, YOSHIKO、KAWAI, KEN-ICHI、NAKAJIMA, SH+

  DOI：——

  日期：——