(+/-)-4-hydroxy-7,8-dimethoxyisochroman-3-one | 676124-27-9

• 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: (+/-)-4-hydroxy-7,8-dimethoxyisochroman-3-one
• 英文别名: 3H-2-Benzopyran-3-one, 1,4-dihydro-4-hydroxy-7,8-dimethoxy-；4-hydroxy-7,8-dimethoxy-1,4-dihydroisochromen-3-one
• CAS: 676124-27-9
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: MZJXPELOWWDCHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-4-hydroxy-7,8-dimethoxyisochroman-3-one 在 咪唑 、 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 4.84h， 生成 (Z)-4-(tert-Butyl-dimethyl-silanyloxy)-4-(2-hydroxymethyl-3,4-dimethoxy-phenyl)-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones

  摘要：

  The elaboration and biological activity of 15, containing the proposed pharmacophore for the antibiotic activity of the pyranonaphthoquinones, are reported. The synthetic strategy involved acid-catalyzed lactonization of mandelate 17 for isochroman ring formation, in combination with a Wittig-oxa-Michael functionalization of isochroman-3-ol derivative 20, a lactonization involving configurational inversion of a benzylic alcohol and a final AgO oxidation. Compound 15 showed activity against Staphylococcus aureus and Bacillus subtilis with MIC of 64 and 32 mug/mL, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.015
• 作为产物：
  描述：

  ethyl (2-acetoxymethyl-3,4-dimethoxyphenyl)glyoxylate 在 camphor-10-sulfonic acid 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 (+/-)-4-hydroxy-7,8-dimethoxyisochroman-3-one
  参考文献：
  名称：

  (±)-4-BROMO-7,8-DIMETHOXY-ISOCHROMAN-3-ONE 的新的和改进的合成，是制备 (±)-cis-ALPININE 和 (±)-cis-ALPINIGENINE 的关键中间体

  摘要：

  Rhoeadine-Papavermbine 生物碱构成一个小家族的天然产物，几乎完全由罂粟属精心制作；这个家族的许多成员都具有潜在的有用生物活性。1982 年，Ahmad 和 Snieckus2 报道了趋同进入罗伊丹骨架和正式全合成 (f)-cis-alpinigenine (1) 和相关的 (*)-cis-alpinine (2)，使用溴内酯 3 作为关键中间体. 溴内酯是由这些作者采用不同的方法制备的；然而，出现了区域选择性问题

  DOI：

  10.1080/00304940409355398

文献信息

• Synthesis of 4-Hydroxy-7,8-dimethoxyisochroman-3-one and Its Plant Growth-Regulating Properties on Tobacco (<i>Nicotiana tabacum</i> cv. Petit Havana)
  作者：Darío A. Bianchi、Nicolás E. Blanco、Néstor Carrillo、Teodoro S. Kaufman

  DOI：10.1021/jf0351117

  日期：2004.4.1

  The synthesis of 6,7-dimethoxy-4-hydroxyisochroman-3-one 10 from 2,3-dimethoxytoluene (11) via glyoxylate 12 is reported. Compound 10 strongly inhibited vegetative growth of tobacco plants, whereas developmental patterns (protein levels, protein profile, pigments, and chlorophylls) were not affected. Morphological changes were observed in the leaves of the treated plants.
• NEW AND IMPROVED SYNTHESIS OF (±)-4-BROMO-7,8-DIMETHOXY-ISOCHROMAN-3-ONE, A KEY INTERMEDIATE FOR THE ELABORATION OF (±)-<i>cis</i>-ALPININE AND (±)-<i>cis</i>-ALPINIGENINE
  作者：DaríO A. Bianchi、Teodoro S. Kaufman

  DOI：10.1080/00304940409355398

  日期：2004.4

  potentially useful biological activity.' In 1982, Ahmad and Snieckus2 reported a convergent entry into the rhoeadan skeleton and a formal total synthesis of (f)-cis-alpinigenine (1) and the related (*)-cis-alpinine (2), using bromolactone 3 as key intermediate. The bromolactone was prepared by these authors employing different approaches; however, regioselectivity problems arising

  Rhoeadine-Papavermbine 生物碱构成一个小家族的天然产物，几乎完全由罂粟属精心制作；这个家族的许多成员都具有潜在的有用生物活性。1982 年，Ahmad 和 Snieckus2 报道了趋同进入罗伊丹骨架和正式全合成 (f)-cis-alpinigenine (1) 和相关的 (*)-cis-alpinine (2)，使用溴内酯 3 作为关键中间体. 溴内酯是由这些作者采用不同的方法制备的；然而，出现了区域选择性问题
• Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones
  作者：Darı́o A. Bianchi、Emma G. Sutich、Teodoro S. Kaufman

  DOI：10.1016/j.bmcl.2003.11.015

  日期：2004.2

  The elaboration and biological activity of 15, containing the proposed pharmacophore for the antibiotic activity of the pyranonaphthoquinones, are reported. The synthetic strategy involved acid-catalyzed lactonization of mandelate 17 for isochroman ring formation, in combination with a Wittig-oxa-Michael functionalization of isochroman-3-ol derivative 20, a lactonization involving configurational inversion of a benzylic alcohol and a final AgO oxidation. Compound 15 showed activity against Staphylococcus aureus and Bacillus subtilis with MIC of 64 and 32 mug/mL, respectively. (C) 2003 Elsevier Ltd. All rights reserved.