7-methylene-4-((4R)-4-phenyl-4,5-dihydrooxazol-2-yl)-5,6-dihydro-7H-cyclopenta[c]pyridine | 936831-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 7-methylene-4-((4R)-4-phenyl-4,5-dihydrooxazol-2-yl)-5,6-dihydro-7H-cyclopenta[c]pyridine
• 英文别名: (4R)-2-(7-methylidene-5,6-dihydrocyclopenta[c]pyridin-4-yl)-4-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 936831-76-4
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: LDFWBVLNOPMREL-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methylene-4-((4R)-4-phenyl-4,5-dihydrooxazol-2-yl)-5,6-dihydro-7H-cyclopenta[c]pyridine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以45%的产率得到(7R)-7-methyl-4-((4R)-4-phenyl-4,5-dihydrooxazol-2-yl)-5,6-dihydro-7H-cyclopenta[c]pyridine
  参考文献：
  名称：

  Neat total synthesis of six monoterpenic alkaloids of the actinidine series

  摘要：

  A concise enantiopure synthesis of six monoterpenic alkaloids of the actinidine series possessing a cyclopenta[c]lpyridine skeleton, (+)-deoxyrhexifoline (4), (+)-boschniakinic acid (5), (+)-boschniakine (6), (-)-plantagonine (7), (-)-indicaine (8) and (-)-tecostidine (9) is reported starting with the chiral precursor 3 -bromo-5 - ((4R)-phenyloxazolin-2-yl)pyridine (10). It involves a C-4 regioselective connection of a butene appendice and an intramolecular 5-exo-trig Heck annulation sequence followed by hydrogenation of the exocyclic alkene. Mixture of (3R)- and (3S)-7-((4R)-phenyloxazolin-2-yl)cyclopenta[clpyridines was separated by HPLC before being transformed into enantiopure natural products (4-9) by modification of the oxazoline group. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.090
• 作为产物：
  描述：

  5-溴烟腈 在 palladium diacetate 1,1'-双(二苯基膦)二茂铁 、 碘 、 氧气 、 magnesium 、 三乙胺 、 silver carbonate 、 zinc(II) chloride 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 氯苯 为溶剂， 反应 100.0h， 生成 7-methylene-4-((4R)-4-phenyl-4,5-dihydrooxazol-2-yl)-5,6-dihydro-7H-cyclopenta[c]pyridine
  参考文献：
  名称：

  Neat total synthesis of six monoterpenic alkaloids of the actinidine series

  摘要：

  A concise enantiopure synthesis of six monoterpenic alkaloids of the actinidine series possessing a cyclopenta[c]lpyridine skeleton, (+)-deoxyrhexifoline (4), (+)-boschniakinic acid (5), (+)-boschniakine (6), (-)-plantagonine (7), (-)-indicaine (8) and (-)-tecostidine (9) is reported starting with the chiral precursor 3 -bromo-5 - ((4R)-phenyloxazolin-2-yl)pyridine (10). It involves a C-4 regioselective connection of a butene appendice and an intramolecular 5-exo-trig Heck annulation sequence followed by hydrogenation of the exocyclic alkene. Mixture of (3R)- and (3S)-7-((4R)-phenyloxazolin-2-yl)cyclopenta[clpyridines was separated by HPLC before being transformed into enantiopure natural products (4-9) by modification of the oxazoline group. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.090

文献信息

• Neat total synthesis of six monoterpenic alkaloids of the actinidine series
  作者：Nicolas Robert、Christophe Hoarau、Francis Marsais

  DOI：10.1016/j.tet.2007.02.090

  日期：2007.4

  A concise enantiopure synthesis of six monoterpenic alkaloids of the actinidine series possessing a cyclopenta[c]lpyridine skeleton, (+)-deoxyrhexifoline (4), (+)-boschniakinic acid (5), (+)-boschniakine (6), (-)-plantagonine (7), (-)-indicaine (8) and (-)-tecostidine (9) is reported starting with the chiral precursor 3 -bromo-5 - ((4R)-phenyloxazolin-2-yl)pyridine (10). It involves a C-4 regioselective connection of a butene appendice and an intramolecular 5-exo-trig Heck annulation sequence followed by hydrogenation of the exocyclic alkene. Mixture of (3R)- and (3S)-7-((4R)-phenyloxazolin-2-yl)cyclopenta[clpyridines was separated by HPLC before being transformed into enantiopure natural products (4-9) by modification of the oxazoline group. (C) 2007 Elsevier Ltd. All rights reserved.