(+)-astropaquinone B2 | 1254107-15-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 英文名称: (+)-astropaquinone B2
• 英文别名: (+)-astropaquinone B；Astropaquinone B；(1R,3S)-1,7,9-trimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione
• CAS: 1254107-15-7
• 化学式: C₁₇H₁₈O₆
• 分子量: 318.326
• InChiKey: ZUCKMONTTODKPQ-WNWIJWBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-astropaquinone B2 在 对甲苯磺酸 作用下， 以 水 、 苯 为溶剂， 反应 4.0h， 以75%的产率得到(+)-astropaquinone C3
  参考文献：
  名称：

  A highly diastereoselective oxa-Pictet-Spengler approach to (+)-astropaquinone B and (+)-astropaquinone C and the formation of astropaquinone B dimer

  摘要：

  A concise and highly diastereoselective synthesis of (+)-astropaquinone B and (+)-astropaquinone C is reported. The synthetic strategy is based on an efficient combination of Dotz benzannulation using a chiral alkyne to construct the naphthalene unit and a highly diastereoselective oxa-Pictet-Spengler reaction to install the trans-configured pyran ring as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.001
• 作为产物：
  描述：

  4-溴-3-甲氧基苯酚 在 正丁基锂 、 四丁基氟化铵 、 sodium hydride 、 对甲苯磺酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.08h， 生成 (+)-astropaquinone B2
  参考文献：
  名称：

  A highly diastereoselective oxa-Pictet-Spengler approach to (+)-astropaquinone B and (+)-astropaquinone C and the formation of astropaquinone B dimer

  摘要：

  A concise and highly diastereoselective synthesis of (+)-astropaquinone B and (+)-astropaquinone C is reported. The synthetic strategy is based on an efficient combination of Dotz benzannulation using a chiral alkyne to construct the naphthalene unit and a highly diastereoselective oxa-Pictet-Spengler reaction to install the trans-configured pyran ring as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.001

文献信息

• Synthesis of the Pyranonaphthoquinones Dehydroherbarin, (+)-Astropa­quinone B and (+)-Astropaquinone C en Route to Ascomycones A and B
  作者：Margaret Brimble、Andrew Wadsworth、Jonathan Sperry

  DOI：10.1055/s-0029-1218832

  日期：2010.8

  The total syntheses of the pyranonaphthoquinone natural products dehydroherbarin, (+)-astropaquinone B and (+)-astropa­quinone C are described. A late stage oxidation strategy employed for the synthesis of the astropaquinones was not amenable to the conversion of dehydroherbarin into the ascomycones. The syntheses of astropaquinones B and C reported herein constitute the first total syntheses and their absolute stereochemistry was determined to be (1R,3S).

  本文描述了脱氢草霉素（dehydroherbarin）、(+)-星棘醌B（(+)-astropaquinone B）和(+)-星棘醌C（(+)-astropaquinone C）三种吡喃萘醌天然产物分子的全合成。在合成星棘醌时使用的后期氧化策略，不适用于将脱氢草霉素转化为囊霉醌（ascomycones）。本文报道的星棘醌B和C的合成是它们的首次全合成，且它们的绝对构型被确定为(1R,3S)。
• A highly diastereoselective oxa-Pictet-Spengler approach to (+)-astropaquinone B and (+)-astropaquinone C and the formation of astropaquinone B dimer
  作者：Rodney A. Fernandes、Sandip V. Mulay

  DOI：10.1016/j.tetasy.2013.09.001

  日期：2013.10

  A concise and highly diastereoselective synthesis of (+)-astropaquinone B and (+)-astropaquinone C is reported. The synthetic strategy is based on an efficient combination of Dotz benzannulation using a chiral alkyne to construct the naphthalene unit and a highly diastereoselective oxa-Pictet-Spengler reaction to install the trans-configured pyran ring as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.