(+/-)-3-(3,4-dimethoxyphenyl)-8-hydroxy-3,4-dihydroisocoumarin | 37568-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-3-(3,4-dimethoxyphenyl)-8-hydroxy-3,4-dihydroisocoumarin
• 英文别名: thunberginol G dimethyl ether；monomethylphylodulcin；3-(3,4-dimethoxy-phenyl)-8-hydroxy-isochroman-1-one；3-(3,4-Dimethoxy-phenyl)-8-hydroxy-isochroman-1-on；Thunberginol H；3-(3,4-dimethoxyphenyl)-8-hydroxy-3,4-dihydroisochromen-1-one
• CAS: 37568-82-4
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: WKNXOKHAEDTQCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  (+/-)-3-(3,4-dimethoxyphenyl)-8-hydroxy-3,4-dihydroisocoumarin 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到Thunberginol G
  参考文献：
  名称：

  Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.09.075
• 作为产物：
  描述：

  (3,4-二甲氧基苄基)-三苯基鏻 氯化物 在 三氯化铝 、 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 (+/-)-3-(3,4-dimethoxyphenyl)-8-hydroxy-3,4-dihydroisocoumarin
  参考文献：
  名称：

  Mali, Raghao S.; Shelke, Dattatray W., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 8, p. 822 - 825

  摘要：

  DOI：

文献信息

• Asahina; Asano, Chemische Berichte, 1929, vol. 62, p. 172,176
  作者：Asahina、Asano

  DOI：——

  日期：——
• JPS54129197A
  申请人：——

  公开号：JPS54129197A

  公开（公告）日：1979-10-06
• Mali, Raghao S.; Shelke, Dattatray W., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 8, p. 822 - 825
  作者：Mali, Raghao S.、Shelke, Dattatray W.

  DOI：——

  日期：——
• 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.