(+/-)-trans-2-(4-hydroxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-yl)acetic acid ethyl ester

• 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: (+/-)-trans-2-(4-hydroxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-yl)acetic acid ethyl ester
• 英文别名: ethyl 2-[(3R,4S)-4-hydroxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-yl]acetate
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: IXTNJJWRBZKGOJ-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-2-(4-hydroxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-yl)acetic acid ethyl ester 在 氢氧化钾 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到
  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 咪唑 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 四丁基氟化铵 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 11.87h， 生成 (+/-)-trans-2-(4-hydroxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-yl)acetic 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

文献信息

• Exploring O-stannyl ketyl and acyl radical cyclizations for the synthesis of γ-lactone-fused benzopyrans and benzofurans
  作者：Helen Santoso、Myriam I. Casana、Christopher D. Donner

  DOI：10.1039/c3ob42090f

  日期：——

  The synthesis of a series of γ-lactone-fused benzopyrans and benzofurans, analogues of the pyranonaphthoquinone antibiotics, is reported. Preparation of the heterocycles was achieved by either O-stannyl ketyl or acyl radical cyclization of benzaldehyde precursors followed by oxidation to give the pyrano- and furanobenzoquinone systems. The observed diastereoselectivity during O-stannyl ketyl radical

  据报道，合成了一系列γ-内酯融合的苯并吡喃和苯并呋喃，它们是吡喃并萘醌抗生素的类似物。杂环的制备是通过苯甲醛前体的O-锡烷基酮基或酰基自由基环化，然后氧化得到吡喃基和呋喃基苯醌体系而实现的。O-锡烷基酮基自由基环化过程中观察到的非对映选择性受醛的芳族取代邻位的影响，而酰基自由基环化然后立体选择性还原所得吡喃酮提供了形成所需的γ-内酯融合的苯并吡喃体系的补充方法。
• Synthesis and antimicrobial activity of pyranobenzoquinones related to the pyranonaphthoquinone antibiotics
  作者：S.H. Lagorio、D.A. Bianchi、E.G. Sutich、T.S. Kaufman

  DOI：10.1016/j.ejmech.2006.06.007

  日期：2006.11

  The synthesis and antimicrobial activity of isochromane-type analogs of the pyranonaphthoquinone antibiotics are reported. Isochromane derivatives with (17a, b) and without (22a, b) a C-4 hydroxyl moiety and their corresponding quinones (19a and 23), were prepared. Both quinones exhibited antimicrobial activity against Staphylococcus aureus, Bacillus atrophaeus and Streptococcus agalactiae, while the related isochromanes were inactive. The results suggest that the quinone moiety is important for biological activity while the C-4 hydroxyl may not be essential. (c) 2006 Elsevier Masson SAS. All rights reserved.