2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4(1H)-pyridinone | 92579-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4(1H)-pyridinone
• 英文别名: 1-triptophyl-2,3-dihydro-1H-pyridin-4-one；1-(2-indol-3-yl-ethyl)-2,3-dihydro-1H-pyridin-4-one；1-<β-(Indolyl-3)-ethyl>-2,3-dihydro-pyridon-4；1-[2-(1H-indol-3-yl)ethyl]-2,3-dihydropyridin-4-one
• CAS: 92579-46-9
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: GNIWRJHACPPSRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4(1H)-pyridinone 在 palladium on activated charcoal 盐酸 、 1,4-diazabicyclo[5.4.0]-7-undecene 、 硫酸 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 44.5h， 生成 (+)-育亨宾
  参考文献：
  名称：

  Total syntheses of yohimbe alkaloids, with stereoselection for the normal, allo, and 3-epiallo series, based on annelations of 4-methoxy-1,2-dihydropyridones

  摘要：

  N-[2-(1H-3-indolyl)ethyl]-2,3-dihydro-4-pyridone (31) was generated in two steps (77% yield) from tryptamine and N-methyl-4-piperidone methiodide. Its cyclization (90% yield) and oxidation (91% yield) provided the tetracyclic analogue 32. O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its N(a)-carbamate) furnished the dienones 38 (64%) and 43 (90%). Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 or 44. Their reductions then led to yohimbinone (52, 20% overall yield from tryptamine), alloyohimbinone (11, 19% overall yield), and 3-epi-alloyohimbinone (10, 23% overall yield), which led to yohimbine (3), beta-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).

  DOI：

  10.1021/jo00008a025
• 作为产物：
  描述：

  1-[2-(1H-吲哚-3-基)乙基]-4-哌啶酮 在 mercury(II) diacetate 作用下， 以90%的产率得到2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4(1H)-pyridinone
  参考文献：
  名称：

  N-烷基取代的4-哌啶酮的乙酸汞氧化将杂环化合物转化为新途径

  摘要：

  N-烷基取代的4-哌啶酮在与乙酸汞反应后容易以高收率进行氧化。描述了将氧化应用于几种生物碱的骨架构架的合成。

  DOI：

  10.1016/j.tetlet.2008.07.109

文献信息

• Synthetic studies on indole alkaloids. II. Applications of phenylsulfonylindoles on intramolecular cyclizations
  作者：Mario Rubiralta、Anna Diez、Cristina Vila

  DOI：10.1016/s0040-4039(00)89061-9

  日期：1990.1

  The synthesis of indolo[2,3-a]quinolizidin-2-one 15 is reported through the potassium tert-butoxide cyclization of N-hydroxyethyl-2-[1-(phenylsulfonyl)-3-indolyl]-4-piperidone ethylene acetal (5) into 3-spiroindolenine intermediate 6. Anhydrous acid treatment of 6 leads to the rearranged 2,3-indole substituted compound 14. The reactivity of intermediate 6 will be further applied to construct ring C

  通过N-羟乙基-2- [1-（苯基磺酰基）-3-吲哚基] -4-哌啶酮乙烯缩醛的叔丁醇钾环化反应，报道了吲哚[2,3 - a ]喹啉基-2-酮15的合成。（5）成3-螺吲哚中间体6。6的无水酸处理导致2,3-吲哚取代的化合物14重排。的中间反应6将进一步施加到构造的环C马钱子和白坚木属框架。
• Synthetic applications of protected 2-aryl-4-piperidones. 7. Synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one
  作者：Mario Rubiralta、Anna Diez、Cristina Vila、Yves Troin、Miguel Feliz

  DOI：10.1021/jo00022a015

  日期：1991.10

  The synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one (1) by the intramolecular cyclization of protected N-(2-hydroxyethyl)-2-[1-(phenylsulfonyl)-3-indolyl]-4-piperidone 15 by the action of K(t)BuO and further acid treatment is reported. The methodology has been first carried out for its deethyl analogue 2 from (hydroxyethyl)piperidine 14 and has shown to be a good general method to reach indolo[2,3-a]quinolizidin-2-one systems. Compound 1 has also been obtained by an unusual rearrangement in acidic medium of 7-ethylhexahydropyrido[1',2':1,2]pyrazino[4,3-a]indole.
• RUBIRALTA, MARIO;DIEZ, ANNA;VILA, CRISTINA, TETRAHEDRON LETT., 31,(1990) N3, C. 3347-3350
  作者：RUBIRALTA, MARIO、DIEZ, ANNA、VILA, CRISTINA

  DOI：——

  日期：——
• KUEHNE, MARTIN E.;MUTH, RANDY S., J. ORG. CHEM., 56,(1991) N, C. 2701-2412
  作者：KUEHNE, MARTIN E.、MUTH, RANDY S.

  DOI：——

  日期：——