Ethyl 5,6-dimethoxy-10-oxo-14,16-dioxatetracyclo[9.7.0.03,8.013,17]octadeca-1(18),3,5,7,11,13(17)-hexaene-2-carboxylate | 912573-37-6

• 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: Ethyl 5,6-dimethoxy-10-oxo-14,16-dioxatetracyclo[9.7.0.03,8.013,17]octadeca-1(18),3,5,7,11,13(17)-hexaene-2-carboxylate
• CAS: 912573-37-6
• 化学式: C₂₁H₂₀O₇
• 分子量: 384.386
• InChiKey: TWUJDSQELZLQRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 5,6-dimethoxy-10-oxo-14,16-dioxatetracyclo[9.7.0.03,8.013,17]octadeca-1(18),3,5,7,11,13(17)-hexaene-2-carboxylate 在 咪唑 、 lithium aluminium tetrahydride 、 L-Selectride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.92h， 生成 (2R,10R)-5,6-dimethoxy-2-[tri(propan-2-yl)silyloxymethyl]-14,16-dioxatetracyclo[9.7.0.03,8.013,17]octadeca-1(18),3,5,7,11,13(17)-hexaen-10-ol
  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：

  (3,4-二甲氧基苯基)乙酰氯 在 dirhodium tetraacetate 吡啶 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 、 cesium fluoride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 Ethyl 5,6-dimethoxy-10-oxo-14,16-dioxatetracyclo[9.7.0.03,8.013,17]octadeca-1(18),3,5,7,11,13(17)-hexaene-2-carboxylate
  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

• Pd-Catalyzed Enantioselective Aerobic Oxidation of Secondary Alcohols: Applications to the Total Synthesis of Alkaloids
  作者：Shyam Krishnan、Jeffrey T. Bagdanoff、David C. Ebner、Yeeman K. Ramtohul、Uttam K. Tambar、Brian M. Stoltz

  DOI：10.1021/ja804738b

  日期：2008.10.15

  Enantioselective syntheses of the alkaloids (-)-aurantioclavine, (+)-amurensinine, (-)-lobeline, and (-)- and (+)-sedamine are described. The syntheses demonstrate the effectiveness of the Pd-catalyzed asymmetric oxidation of secondary alcohols in diverse contexts and the ability of this methodology to set the absolute configuration of multiple stereocenters in a single operation. The utility of an

  描述了生物碱 (-)-aurantioclavine、(+)-amurensinine、(-)-lobeline 和 (-)- 和 (+)-sedamine 的对映选择性合成。合成证明了 Pd 催化的仲醇不对称氧化在不同环境中的有效性，以及该方法在单个操作中设置多个立体中心的绝对构型的能力。还描述了芳烃 CC 插入反应在访问复杂多环框架中的效用。
• 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.