(3E,6S,7S,8R,9Z)-12-{2,5-dimethoxy-3-[(3R,4E)-3-methoxyhepta-4,6-dienamido]phe-nyl}-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl1-[(cyclohex-1-ene)amido]cyclopropane-1-carboxylate | 1270942-86-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3E,6S,7S,8R,9Z)-12-{2,5-dimethoxy-3-[(3R,4E)-3-methoxyhepta-4,6-dienamido]phe-nyl}-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl1-[(cyclohex-1-ene)amido]cyclopropane-1-carboxylate
• 英文别名: [(3E,6S,7S,8R,9Z)-12-[2,5-dimethoxy-3-[[(3R,4E)-3-methoxyhepta-4,6-dienoyl]amino]phenyl]-8-[(4-methoxyphenyl)methoxy]-7,9-dimethyldodeca-1,3,9-trien-6-yl] 1-(cyclohexene-1-carbonylamino)cyclopropane-1-carboxylate
• CAS: 1270942-86-3
• 化学式: C₄₉H₆₄N₂O₉
• 分子量: 825.055
• InChiKey: XJRSEBFSOBJKSJ-GLWFVFQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  60
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3E,6S,7S,8R,9Z)-12-{2,5-dimethoxy-3-[(3R,4E)-3-methoxyhepta-4,6-dienamido]phe-nyl}-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl1-[(cyclohex-1-ene)amido]cyclopropane-1-carboxylate 在 双(三环己基磷)-3-苯基-1H-茚二氯化钌 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到[(5R,6E,8E,10E,13S,14S,15R,16Z)-5,22,24-trimethoxy-15-[(4-methoxyphenyl)methoxy]-14,16-dimethyl-3-oxo-2-azabicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20(24),21-heptaen-13-yl] 1-(cyclohexene-1-carbonylamino)cyclopropane-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 1,3-丙二硫醇 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 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 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 二甲基氯化铝 、 caesium carbonate 、 高碘酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 1,2-双(二苯基膦)乙烷 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 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 161.84h， 生成 (3E,6S,7S,8R,9Z)-12-{2,5-dimethoxy-3-[(3R,4E)-3-methoxyhepta-4,6-dienamido]phe-nyl}-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl1-[(cyclohex-1-ene)amido]cyclopropane-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.