8,9-dimethoxy-2,3-(methylenedioxy)isopavinane | 101608-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 8,9-dimethoxy-2,3-(methylenedioxy)isopavinane
• 英文别名: 14,15-dimethoxy-5,7-dioxa-19-azapentacyclo[9.7.2.02,10.04,8.012,17]icosa-2,4(8),9,12,14,16-hexaene
• CAS: 101608-94-0
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: QPVUNAZVNLQLAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  48.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 8,9-dimethoxy-2,3-(methylenedioxy)isopavinane 在 sodium cyanoborohydride 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以1.5 mg的产率得到Amurensinin
  参考文献：
  名称：

  A Convergent and Enantioselective Synthesis of (+)-Amurensinine via Selective C−H and C−C Bond Insertion Reactions

  摘要：

  A convergent and enantioselective synthesis of the natural product amurensinine is described. The synthetic strategy takes advantage of mild and selective C-H and C-C bond insertion reactions, in addition to the palladium-catalyzed aerobic oxidative kinetic resolution recently developed in these laboratories.

  DOI：

  10.1021/ja0651815
• 作为产物：
  描述：

  在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 23.0~60.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 8,9-dimethoxy-2,3-(methylenedioxy)isopavinane
  参考文献：
  名称：

  A Convergent and Enantioselective Synthesis of (+)-Amurensinine via Selective C−H and C−C Bond Insertion Reactions

  摘要：

  A convergent and enantioselective synthesis of the natural product amurensinine is described. The synthetic strategy takes advantage of mild and selective C-H and C-C bond insertion reactions, in addition to the palladium-catalyzed aerobic oxidative kinetic resolution recently developed in these laboratories.

  DOI：

  10.1021/ja0651815

文献信息

• A Simple and Efficient Synthetic Route to Chiral Isopavines. Synthesis of (−)-<i>O</i>-Methylthalisopavine and (−)-Amurensinine
  作者：Luisa Carrillo、Dolores Badía、Esther Domínguez、José L. Vicario、Imanol Tellitu

  DOI：10.1021/jo9708102

  日期：1997.10.1

  The isopavinan alkaloids (-)-O-methylthalisopavine (7a) and (-)-amurensinine (7d) have been synthesized in good yield and high ee from the appropriate 1,2-diarylethylamine derivatives using optically active beta-amino alcohols as chiral support. This synthetic route employs as key steps the alkylation reaction of the azomethine derivatives 2 with Grignard reagents 1 and a novel one-pot double-intramolecular cyclization of the adequately functionalized 1,2-diarylethylamines 5 to afford a series of optically active isopavines 6a-d and 7a-d.
• A Convergent and Enantioselective Synthesis of (+)-Amurensinine via Selective C−H and C−C Bond Insertion Reactions
  作者：Uttam K. Tambar、David C. Ebner、Brian M. Stoltz

  DOI：10.1021/ja0651815

  日期：2006.9.1

  A convergent and enantioselective synthesis of the natural product amurensinine is described. The synthetic strategy takes advantage of mild and selective C-H and C-C bond insertion reactions, in addition to the palladium-catalyzed aerobic oxidative kinetic resolution recently developed in these laboratories.