(3aR,5R,11bR)-6,7,11-trimethoxy-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one | 1404583-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (3aR,5R,11bR)-6,7,11-trimethoxy-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one
• 英文别名: (3aR,5R,11bR)-3,3a,5,11b-tetrahydro-6,7,11-trimethoxy-5-propyl-1,4-dioxacyclopent[a]anthracen-2-one；(11R,15R,17R)-2,4,9-trimethoxy-17-propyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1,3(8),4,6,9-pentaen-13-one
• CAS: 1404583-71-6
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: DVBSHQWPHCMBAI-JZKQVHKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,5R,11bR)-6,7,11-trimethoxy-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 生成 (3aR,5S,11bR)-3,3a,5,11b-tetrahydro-7-methoxy-5-propyl-1,4-dioxacyclopent[a]anthracen-2,6,11-trione
  参考文献：
  名称：

  A Diastereoselective Oxa-Pictet–Spengler-Based Strategy for (+)-Frenolicin B and epi-(+)-Frenolicin B Synthesis

  摘要：

  An efficient diastereoselective oxa-Pictet - Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.

  DOI：

  10.1021/ol4027649
• 作为产物：
  描述：

  1,5-二羟基萘 在 吡啶 、 sodium dithionite 、 二(三叔丁基膦)钯 、 甲基磺酰胺 、 AD-mix-β 、 N-甲基二环己基胺 、 palladium on activated charcoal 、 三氟化硼乙醚 、 四丁基溴化铵 、 水 、 氢气 、 二氯乙基铝 、 碳酸氢钠 、 对甲苯磺酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 、 叔丁醇 为溶剂， 反应 81.84h， 生成 (3aR,5R,11bR)-6,7,11-trimethoxy-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one
  参考文献：
  名称：

  A Diastereoselective Oxa-Pictet–Spengler-Based Strategy for (+)-Frenolicin B and epi-(+)-Frenolicin B Synthesis

  摘要：

  An efficient diastereoselective oxa-Pictet - Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.

  DOI：

  10.1021/ol4027649

文献信息

• A Chiron Approach to the Total Synthesis of (−)-Juglomycin A, (+)-Kalafungin, (+)-Frenolicin B, and (+)-Deoxyfrenolicin
  作者：Rodney A. Fernandes、Vijay P. Chavan、Sandip V. Mulay、Amarender Manchoju

  DOI：10.1021/jo3019939

  日期：2012.11.16

  A general, efficient, and common strategy for the synthesis of (−)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, d-glucono-δ-lactone, Dötz benzannulation, oxa-Pictet-Spengler reaction, and H2SO4-mediated epimerization.

  此处报道了合成（-）-珠红霉素A，（+）-卡拉芬净，（+）-肾上腺素B和（+）-脱氧肾上腺素的通用，有效且通用的策略。该策略涉及由廉价的手性池材料，d-葡萄糖酸-δ-内酯，Dötz苯环化，oxa-Pictet-Spengler反应和H 2 SO 4介导的差向异构化合成关键的结构单元炔烃。
• A Diastereoselective Oxa-Pictet–Spengler-Based Strategy for (+)-Frenolicin B and <i>epi</i>-(+)-Frenolicin B Synthesis
  作者：Yinan Zhang、Xiachang Wang、Manjula Sunkara、Qing Ye、Larissa V. Ponomereva、Qing-Bai She、Andrew J. Morris、Jon S. Thorson

  DOI：10.1021/ol4027649

  日期：2013.11

  An efficient diastereoselective oxa-Pictet - Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.