6-(4-methoxyphenyl)-2,3,8,8a-tertahydroindolizin-7(1H)-one | 87264-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(4-methoxyphenyl)-2,3,8,8a-tertahydroindolizin-7(1H)-one
• 英文别名: 6-(4-methoxyphenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one；2,3,8,9-tetrahydro-6-(4-methoxyphenyl)indolizin-7(1H)-one；6-(4-methoxyphenyl)-2,3,8,8a-tetrahydro-1H-indolizin-7-one
• CAS: 87264-40-2
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: MTEFHBANSTWWSG-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  402.0±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-methoxyphenyl)-2,3,8,8a-tertahydroindolizin-7(1H)-one 在 氨 、 lithium 作用下， 以54%的产率得到1-aza-3-(4-methoxyphenyl)bicyclo<4,3,0>nonan-4-one
  参考文献：
  名称：

  FORMAL SYNTHESIS OF (±)-IPALBIDINE

  摘要：

  1-Aza-3-(4-甲氧基苯基)双环[4,3,0]壬南-4-酮是(±)-ipalbidine的关键中间体，通过N-甲酰酮的分子内环化方便地合成，该酮通过[ 3+2]环状硝酮的环加成反应。

  DOI：

  10.1246/cl.1983.1195
• 作为产物：
  描述：

  4-烯丙基苯甲醚 在 palladium on activated charcoal 氨 、 氢气 、 aluminum tri-tert-butoxide 作用下， 以 二氯甲烷 、 甲苯 、 xylene 为溶剂， 生成 6-(4-methoxyphenyl)-2,3,8,8a-tertahydroindolizin-7(1H)-one
  参考文献：
  名称：

  FORMAL SYNTHESIS OF (±)-IPALBIDINE

  摘要：

  1-Aza-3-(4-甲氧基苯基)双环[4,3,0]壬南-4-酮是(±)-ipalbidine的关键中间体，通过N-甲酰酮的分子内环化方便地合成，该酮通过[ 3+2]环状硝酮的环加成反应。

  DOI：

  10.1246/cl.1983.1195

文献信息

• Copper-Assisted Palladium(II)-Catalyzed Direct Arylation of Cyclic Enaminones with Arylboronic Acids
  作者：Yong Wook Kim、Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/jo301531k

  日期：2012.11.2

  Described herein is a palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids. The versatility of this method is that both electron-rich and electron-poor boronic acids can be coupled in high yields. A mixture of two Cu(II) additives was crucial for efficient cross-coupling. The role of each Cu(II) reagent appears to be distinct and complementary serving to assist catalyst

  本文描述的是钯(II)-催化的环状烯胺酮与芳基硼酸的直接芳基化。这种方法的多功能性在于富电子和缺电子硼酸都可以高产率耦合。两种 Cu(II) 添加剂的混合物对于有效的交叉耦合至关重要。每个 Cu(II) 试剂的作用似乎是不同的和互补的，有助于通过假定的芳基铜中间体帮助催化剂再氧化和金属转移。
• FORMAL SYNTHESIS OF (±)-IPALBIDINE
  作者：Hideo Iida、Yohya Watanabe、Chihiro Kibayashi

  DOI：10.1246/cl.1983.1195

  日期：1983.8.5

  1-Aza-3-(4-methoxyphenyl)bicyclo[4,3,0]nonan-4-one, key intermediate to (±)-ipalbidine, was conveniently synthesized by intramolecular cyclization of the N-formyIketone which was obtained via [3 + 2] cycloaddition reaction of the cyclic nitrone.

  1-Aza-3-(4-甲氧基苯基)双环[4,3,0]壬南-4-酮是(±)-ipalbidine的关键中间体，通过N-甲酰酮的分子内环化方便地合成，该酮通过[ 3+2]环状硝酮的环加成反应。
• Microwave-assisted Suzuki–Miyaura couplings on α-iodoenaminones
  作者：Xin Wang、Brandon J. Turunen、Matthew W. Leighty、Gunda I. Georg

  DOI：10.1016/j.tetlet.2007.10.078

  日期：2007.12

  A systematic study of alpha-iodination and subsequent Suzuki-Miyaura couplings between non-attenuated enaminones and a wide range of aromatic boronic acids is reported. The microwave-assisted variant of this transformation furnished the alpha-arylenaminones in significantly shorter reaction times and slightly improved yields as compared to conventional heating. (C) 2007 Elsevier Ltd. All rights reserved.
• Palladium(II)-Catalyzed Direct Arylation of Enaminones Using Organotrifluoroborates
  作者：Haibo Ge、Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/ja710221c

  日期：2008.3.1

  A Pd(II)-catalyzed reaction for the direct aryation of cyclic enaminones is reported. The reactivity of electron-rich, electron-poor, and sterically encumbered organotrifluoroborates was investigated. This reaction represents a unique use for organotrifluoroborates as coupling partners and discloses the utility of enaminones for direct-functionalization reactions. It provides immediate access to arylpiperidine, indolizidine, and quinolizidine scaffolds from the corresponding mono- and bicyclic, unattenuated enaminones.
• Iida, Hideo; Watanabe, Yohya; Kibayashi, Chihiro, Journal of the Chemical Society. Perkin transactions I, 1985, p. 261 - 266
  作者：Iida, Hideo、Watanabe, Yohya、Kibayashi, Chihiro

  DOI：——

  日期：——