3-(3',4',5'-trimethoxyphenyl)-8-hydroxy-3,4-dihydrobenzopyran-1-one

• 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-(3',4',5'-trimethoxyphenyl)-8-hydroxy-3,4-dihydrobenzopyran-1-one
• 英文别名: (±)-macrophyllol；macrophyllol；8-hydroxy-3-(3,4,5-trimethoxyphenyl)-3,4-dihydroisochromen-1-one
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: IYIYVLQFGNRYQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  3-(3',4',5'-trimethoxyphenyl)-8-hydroxy-3,4-dihydrobenzopyran-1-one 、 碳酸氢钠 生成 2-hydroxy-6-[(2R)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]benzoic acid
  参考文献：
  名称：

  HASHIMOTO, TOSHIHIRO;TORI, MOTOO;ASAKAWA, YOSHINORI, PHYTOCHEMISTRY, 26,(1987) N 12, 3323-3330

  摘要：

  DOI：
• 作为产物：
  描述：

  (3-acetyloxy-2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide 在 氢氧化钾 、 sodium ethanolate 、 三氟乙酸 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 76.0h， 生成 3-(3',4',5'-trimethoxyphenyl)-8-hydroxy-3,4-dihydrobenzopyran-1-one
  参考文献：
  名称：

  Efficient syntheses of (±)-hydrangenol, (±)-phyllodulcin and (±)-macrophyllol

  摘要：

  In this paper we report on a efficient and flexible synthetic route towards the total syntheses of the dihydrocoumarine derivatives hydrangenol (1), phyllodulcin (1a) and macrophyllol (6b). The syntheses started with a readily available phosphonium salt 2 and suitable modified benzaldehydes 3/3a/3b resulting in 46 to 61% overall yields in three to four-steps sequences. The racemic products could be separated by chiral HPLC. The evidence of the(R)-enantiomer for sweetness could be demonstrated for la. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.046

文献信息

• Synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins via successive lateral and ortho-lithiations of 4,4-dimethyl-2-(o-tolyl)oxazoline
  作者：Naruki Tahara、Tsutomu Fukuda、Masatomo Iwao

  DOI：10.1016/j.tetlet.2004.04.158

  日期：2004.6

  of 4,4-dimethyl-2-(o-tolyl)oxazoline in THF with sec-BuLi, aromatic or aliphatic aldehydes, sec-BuLi, B(OMe)3, and H2O2 produced the laterally alkylated and ortho-hydroxylated oxazolines in one-pot. Treatment of these products with TFA in aqueous THF provided 3-substituted 8-hydroxy-3,4-dihydroisocoumarins in 44–75% overall yields. This procedure allowed the short synthesis of (±)-hydrangenol and (±)-phyllodulcin

  用仲-BuLi，芳族或脂族醛，仲-BuLi，B（OMe）3和H 2 O 2依次处理THF中的4,4-二甲基-2-（邻甲苯基）恶唑啉，生成侧烷基化和邻位一锅中的-羟基化的恶唑啉。用TFA在THF水溶液中处理这些产品可提供3-取代的8-羟基-3,4-二氢异香豆素，总产率为44-75％。该方法允许短合成（±）-羟基和（±）-叶绿素，它们是天然存在的具有药理学意义的3,4-二氢异香豆素。还描述了通过三阴离子中间体更经济地合成（±）-叶绿素。
• Three dihydroisocoumarin glucosides from Hydrangea macrophylla subsp. serrata
  作者：Toshihiro Hashimoto、Motoo Tori、Yoshinori Asakawa

  DOI：10.1016/s0031-9422(00)82497-8

  日期：1987.1

  Abstract Three new dihydroisocoumarin glucosides, macrophyllosides A, B and C were obtained from dry leaves of Hydrangea macrophylla subsp. serrata, together with the previously known hydrangenol 8-β-glucoside. Using NMR and CD techniques and some chemical transformation, the structures were elucidated as (3S)-3′,4′,5′-trimethoxyphenyl-8-β- D -glucopyranosyl dihydroisocoumarin, (3R and (3S)-3′,5′-

  摘要 从大叶绣球亚种的干叶中获得了三种新的二氢异香豆素糖苷，大叶苷A、B和C。锯齿，连同先前已知的 hydrangenol 8-β-glucoside。使用NMR和CD技术以及一些化学转化，结构被阐明为(3S)-3',4',5'-三甲氧基苯基-8-β-D-吡喃葡萄糖基二氢异香豆素，(3R和(3S)-3',5 '-二甲氧基-4'-羟基苯基-8-β-D-吡喃葡萄糖基二氢异香豆素.CD实验表明，八氢紫杉醇8-β-葡萄糖苷是3S-和3R-立体异构体的混合物。
• Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G
  作者：Samir Kumar Mandal、Subhas Chandra Roy

  DOI：10.1016/j.tet.2008.09.075

  日期：2008.12

  A radical-promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of four naturally occurring dihydrocoumarins hydrangenol, phyllodulcin, macrophyllol and thunberginol G has been accomplished using the radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon. (C) 2008 Elsevier Ltd. All rights reserved.
• HASHIMOTO, TOSHIHIRO;TORI, MOTOO;ASAKAWA, YOSHINORI, PHYTOCHEMISTRY, 26,(1987) N 12, 3323-3330
  作者：HASHIMOTO, TOSHIHIRO、TORI, MOTOO、ASAKAWA, YOSHINORI

  DOI：——

  日期：——
• Efficient syntheses of (±)-hydrangenol, (±)-phyllodulcin and (±)-macrophyllol
  作者：Mehmet Günes、Andreas Speicher

  DOI：10.1016/j.tet.2003.09.046

  日期：2003.10

  In this paper we report on a efficient and flexible synthetic route towards the total syntheses of the dihydrocoumarine derivatives hydrangenol (1), phyllodulcin (1a) and macrophyllol (6b). The syntheses started with a readily available phosphonium salt 2 and suitable modified benzaldehydes 3/3a/3b resulting in 46 to 61% overall yields in three to four-steps sequences. The racemic products could be separated by chiral HPLC. The evidence of the(R)-enantiomer for sweetness could be demonstrated for la. (C) 2003 Elsevier Ltd. All rights reserved.