(3E,6R,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl 1-azidocyclopropane-1-carboxylate | 1270942-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3E,6R,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl 1-azidocyclopropane-1-carboxylate
• 英文别名: [(3E,6S,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-[(4-methoxyphenyl)methoxy]-7,9-dimethyldodeca-1,3,9-trien-6-yl] 1-azidocyclopropane-1-carboxylate
• CAS: 1270942-82-9
• 化学式: C₃₄H₄₂N₄O₈
• 分子量: 634.729
• InChiKey: ZBWYPGORHCCAKA-FEOUYTKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3E,6R,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl 1-azidocyclopropane-1-carboxylate 在 1,3-丙二硫醇 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以89%的产率得到(3E,6R,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl 1-aminocyclopropane-1-carboxylate
  参考文献：
  名称：

  Synthesis of the Cytotrienin A CoreviaMetal Catalyzed C−C Coupling

  摘要：

  A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which Is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.

  DOI：

  10.1021/ol200160p
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基-3-硝基苯 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 二甲基氯化铝 、 caesium carbonate 、 高碘酸 、 三乙胺 、 三苯基膦 、 1,2-双(二苯基膦)乙烷 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 93.84h， 生成 (3E,6R,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl 1-azidocyclopropane-1-carboxylate
  参考文献：
  名称：

  Synthesis of the Cytotrienin A CoreviaMetal Catalyzed C−C Coupling

  摘要：

  A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which Is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.

  DOI：

  10.1021/ol200160p

文献信息

• Synthesis of the Cytotrienin A Core<i>via</i>Metal Catalyzed C−C Coupling
  作者：Michael Rössle、David J. Del Valle、Michael J. Krische

  DOI：10.1021/ol200160p

  日期：2011.3.18

  A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which Is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.