Peshawarin | 63950-18-5

• 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: Peshawarin
• 英文别名: (+/-)-Peshawarine；7-[6-[2-(Dimethylamino)ethyl]-1,3-benzodioxol-5-yl]-6,7-dihydro-[1,3]dioxolo[4,5-h]isochromen-9-one
• CAS: 63950-18-5
• 化学式: C₂₁H₂₁NO₆
• 分子量: 383.401
• InChiKey: CVFMLLFLGTVLGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  572.2±50.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Methyl 6-formyl-2,3-(methylenedioxy)benzoate 在 Raney nickel W-2 sodium hydroxide 、 正丁基锂 、 三氟化硼乙醚 、 二异丙胺 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 6.5h， 生成 Peshawarin
  参考文献：
  名称：

  Synthesis of secoisoquinoline alkaloids total synthesis of peshawarine

  摘要：

  DOI：

  10.1016/s0040-4020(01)96087-9

文献信息

• Reaction of Benzocyclobutene Oxides with Aldehydes: Synthesis of Peshawarine and Other 3,4-Dihydroisocoumarins
  作者：John J. Fitzgerald、Alex R. Pagano、Vianne M. Sakoda、R. A. Olofson

  DOI：10.1021/jo00094a022

  日期：1994.7

  Deprotonation of benzocyclobutenols 6 in the presence of aromatic aldehydes affords benzopyranols 7 in high yield. In the key step of this process, an o-tolualdehyde anion generated by the known ring-opening of benzocyclobutenoxides adds to the aldehyde to give 7 which is easily oxidized to 3-substituted 3,4-dihydroisocoumarins 8 including intermediates in some natural product syntheses. For example, reaction of 6-methoxybenzocyclobutenol (1) with LTMP and p-anisaldehyde gave in 96% yield the benzopyranol 16, which subsequently was converted to (+/-)-hydrangenol (17). Similar treatment of 1 with LDA and isovanillin benzyl ether afforded the benzopyranol 19 (87% yield) which already has been converted to (+/-)-phyllodulcin (21). Finally, reaction of 5,6-(methylenedioxy)-benzocyclobutenol (10) with LTMP and the aldehyde 26 (from treatment of hydrastinine with ClCO2-Me) followed by methanolysis produced the acetal 28 in 96% yield. The overall yield was 65% for the five-step synthesis of the alkaloid (+/-)-peshawawine (24) from 10 and 26. Extension of the process to aliphatic aldehydes was illustrated by the preparation of 32 from benzocyclobutenol and isobutyraldehyde in 69% overall yield after oxidation with PCC.
• Synthesis of secoisoquinoline alkaloids total synthesis of peshawarine
  作者：Maria Chrzanowska、Maria D. Rozwadowska

  DOI：10.1016/s0040-4020(01)96087-9

  日期：1986.1