(3aR,3a'R,3a''R,8aS,8a'S,8a''S)-2,2',2''-(propane-1,2,2-triyl)tris(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) | 1278594-21-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3aR,3a'R,3a''R,8aS,8a'S,8a''S)-2,2',2''-(propane-1,2,2-triyl)tris(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)
• 英文别名: (3aS,8bR)-2-[1,2-bis[(3aS,8bR)-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-yl]propan-2-yl]-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazole
• CAS: 1278594-21-0
• 化学式: C₃₃H₂₉N₃O₃
• 分子量: 515.612
• InChiKey: YLOSTUMAQZEZMP-DTWWJVOBSA-N

物化性质

• 熔点：
  117-120 °C
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (+)-2,2'-亚甲基双[(3aR,8aS)-3a,8a-二氢-8H-茚苯[1,2-d]并恶唑 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.25h， 生成 (3aR,3a'R,3a''R,8aS,8a'S,8a''S)-2,2',2''-(propane-1,2,2-triyl)tris(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)
  参考文献：
  名称：

  An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion

  摘要：

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.

  DOI：

  10.1021/ol200402m
• 作为试剂：
  描述：

  苯甲醛腙 在 4-二甲氨基吡啶 、 草酰氯 、 (3aR,3a'R,3a''R,8aS,8a'S,8a''S)-2,2',2''-(propane-1,2,2-triyl)tris(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 红铝 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 (S)-((1S,2S)-2-phenylcyclooctyl)-α-acetyl mandelate
  参考文献：
  名称：

  An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion

  摘要：

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.

  DOI：

  10.1021/ol200402m

文献信息

• Lewis Acid Catalysed Asymmetric One-Carbon Ring-Expansion of Prochiral Cyclobutanones
  作者：Johannes M. Wahl、Marius Tenberge

  DOI：10.1055/s-0042-1751386

  日期：2023.3

  Enantioselective methylene insertion into prochiral cyclobutanones is described providing access to chiral β-substituted cyclopentanones as important structural motif in synthesis and natural products. Commercially available trimethylsilyl as well as other silyl diazomethanes act as one-carbon synthon and scandium triflate is found to be a potent Lewis acid catalyst. By using bis(oxazoline) ligands, enantioinduction is achieved for a number of β-substituted cyclopentanones including examples bearing all-carbon quaternary stereocentres.

  摘要：本文描述了手性β-取代环戊酮的亲核亚甲基插入反应，提供了在合成和天然产物中作为重要结构基元的手性β-取代环戊烯酮的访问途径。商业上可获得的三甲基硅基以及其他硅基重氮甲烷作为一碳合成物，而三氟甲基硫酸钪则被发现是一种有效的路易斯酸催化剂。通过使用双噁唑啉配体，实现了对许多β-取代环戊烯酮的对映诱导，包括带有全碳季节立体中心的例子。
• An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion
  作者：Victor L. Rendina、David C. Moebius、Jason S. Kingsbury

  DOI：10.1021/ol200402m

  日期：2011.4.15

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.